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Inviting, two-story home with a large yard, sunroom, balcony, & washer/dryer Oak Bluffs, Massachusetts

Inviting, two-story home with a large yard, sunroom, balcony, & washer/dryer

Located in Oak Bluffs, Massachusetts, United States. Inviting, two-story home with a large yard, sunroom, balcony, & washer/dryer Gingerbread DreamOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Experience the laidback lifestyle of the Vineyard from this classic, two-story Oak Bluffs vacation rental! Located just a short walk from downtown and the ferry, this home is ideal for those seeking easy access to the coast, local beaches, and an abundance of other family-friendly attractions. Enjoy a leisurely bike ride, check out the Flying Horses Carousel (the oldest platform carousel in the country!), then spend your afternoon swimming in the warm waters of Nantucket Sound. Or, venture to Joseph Sylvia State Beach, ideal for beachcombing, windsurfing, and fishing for striped bass. Timeless attractions like Martha's Vineyard Performing Arts Center, Flying Horses Carousel, Reliable Market, and Inkwell Beach are all within a three-mile radius. Or check out Ob

🛏 3 beds · 👥 8 guests
$279 /night
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#CozyBluffs #OakBluffs #EastChop 1 BD, 1.5 bath home-Walk to Town-Ferries-Beach! Oak Bluffs, Massachusetts

#CozyBluffs #OakBluffs #EastChop 1 BD, 1.5 bath home-Walk to Town-Ferries-Beach!

Located in Oak Bluffs, Massachusetts, United States. #CozyBluffs #OakBluffs #EastChop 1 BD, 1.5 bath home-Walk to Town-Ferries-Beach! Introducing our #CozyBluffs home in Oak Bluffs on Martha's Vineyard! Designed by local Architect Chuck Sullivan and built in 2013 #CozyBluffs is nestled in a quaint, historic Oak Bluffs residential neighborhood and #CozyBluffs is walking distance to Circuit Ave, Hi-Speed and Auto Ferry and town beach!This 755 Sq Ft split level standalone house has one large bedroom with a custom Saatva Cal King bed, ensuite bath and balcony. There is a flex space loft with reading niche, desk/work area so you can work and play! The first floor features an open concept living, kitchen and dining areas & a 1/2 bath. There is a full basement accessed from the living room with washer/dryer/drying rack/iron and ironing board. Private and enclosed outdoor area includes an expansive private backyard with BBQ, dining and seating areas, and outdoor shower. There is a parking area in front of the house. #CozyBluffs is located only

🛏 1 bed · 👥 2 guests
$343 /night
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Oak Bluffs Family Retreat - Private Roundabout, Walk to the Beach & Downtown OB. Oak Bluffs, Massachusetts

Oak Bluffs Family Retreat - Private Roundabout, Walk to the Beach & Downtown OB.

Located in Oak Bluffs, Massachusetts, United States. Oak Bluffs Family Retreat - Private Roundabout, Walk to the Beach & Downtown OB. Renovated in 2022, The Panola House is tucked away on a private lot with its own roundabout driveway. Walk to the center of Oak Bluffs and the OB Ferry. (Scenic 15 minute walk brings you to the Historic Campground, right behind the center of Downtown OB, Circuit Avenue .) Inkwell Beach is a short 5-10 minute walk from there, if you don’t stop for ice cream :) Each location above is accessible by bike in 7 minutes and car in less than 10 minutes. The 1st floor has 1,500 sq. ft of living space with an additional 1,500 in the finished lower level, perfect for family time, children, teenagers and adults. There is a 65 inch TV that connects to Sling TV for cable and Netflix. (Media & entertainment, board games, and movies.).The lower level also has a pullout full-sized bed and a 1/2 bathroom in addition to the three bedrooms on the 1st floor. Central A/C throughout the house (installed in 2022). The outdoor

🛏 3 beds · 👥 6 guests
$739 /night
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Serene home with backyard barbecue area - bike to Arts District, 1 mile to beach Oak Bluffs, Massachusetts

Serene home with backyard barbecue area - bike to Arts District, 1 mile to beach

Located in Oak Bluffs, Massachusetts, United States. Serene home with backyard barbecue area - bike to Arts District, 1 mile to beach Vineyard HavenOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This charming home on Martha's Vineyard is the perfect destination for your next family getaway. You'll enjoy a huge backyard with a private hedge, a picnic table, and a grill for summer cookouts, along with a private porch and terrace. Inside, you'll find two living rooms with plenty of seating for bonding time and a TV with cable and a DVD player for movie nights.What's Nearby:This home lies on the northeastern shore of Martha's Vineyard, about one mile from Inkwell Beach. You'll be within a short walk or bike ride from the Oak Bluff's Arts District, Circuit Avenue, and numerous restaurants, including Smoke n' Bones BBQ and the fabled Tony's Market.Things to Know:Full kitchen (with dishwasher)If you are bringing a dog on your trip, the pet fee is already in

🛏 4 beds · 👥 8 guests
$255 /night
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Great location, happy house 0.5 mile Nancy’s & Jetty Beach. Oak Bluffs, Massachusetts

Great location, happy house 0.5 mile Nancy’s & Jetty Beach.

Located in Oak Bluffs, Massachusetts, United States. Great location, happy house 0.5 mile Nancy’s & Jetty Beach. 1900's Victorian, renovated and newly furnished. House is located on New York Ave, which is the main road between Oak Bluffs and Vineyard Haven. The bus goes past the house every twenty minutes during the summer and can be flagged. House is approximately 1,600 square feet. House purchased in 2018 and all furnishings and furniture is new. Kitchen and down stairs bathroom are newly renovated! First floor includes living room with 50" HDTV, and two large coaches. It is connected to den with sleeper sofa, coffee table, table to play games/puzzles and sitting chair to enjoy a book. Kitchen is eat-in and includes various appliances, including blender, toaster, coffee maker, microwave. Off the kitchen is a bathroom with shower, toilet and sink.Three upstairs bedrooms: 1) master bedroom with small futon, pack and play or air mattress, queen size bed, dresser and side table and closet 2) queen size bed with side table, dresser and

🛏 3 beds · 👥 8 guests
$211 /night
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COZY 3 BR/2 BA CAPE COD IN QUIET NEIGHBORHOOD. CLOSE TO OB CENTER AND LAGOON. Oak Bluffs, Massachusetts

COZY 3 BR/2 BA CAPE COD IN QUIET NEIGHBORHOOD. CLOSE TO OB CENTER AND LAGOON.

Located in Oak Bluffs, Massachusetts, United States. COZY 3 BR/2 BA CAPE COD IN QUIET NEIGHBORHOOD. CLOSE TO OB CENTER AND LAGOON. Located in the beautiful Lagoon Heights neighborhood, you'll enjoy this lovely 3 Bedroom, 2 Bath cozy Cape Cod home with a finished basement within walking distance of Oak Bluffs Center and the Lagoon at the end of the road. The house has been renovated with a new kitchen and new bathrooms and beautifully decorated with all new furniture, etc.This desirable location includes a first-floor primary bedroom with a Queen size bed and two bedrooms with two twins each (which can be converted to King beds) on the second floor. The partially finished basement provides additional living space for the family to enjoy and a dedicated remote work space. The kitchen is the perfect space for gathering after a fun filled day at any of the beautiful beaches on Martha's Vineyard. There is a newly renovated deck off the kitchen that is just right for grilling and enjoying a cocktail.The home is centrally located within a few m

🛏 3 beds · 👥 6 guests
$464 /night
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Private Beach Waterfront Oak-Bluffs Family Cottage Oak Bluffs, Massachusetts

Private Beach Waterfront Oak-Bluffs Family Cottage

Located in Oak Bluffs, Massachusetts, United States. Private Beach Waterfront Oak-Bluffs Family Cottage Experience the magic of Martha's Vineyard from our beachfront retreat. Nestled in a quiet neighborhood, yet conveniently close to Oak Bluffs, you'll find the perfect balance of seclusion and accessibility. Wake up to stunning views of the Lagoon and end your day with unparalleled sunsets reflecting off of the still water. *2024 Season Update - Air conditioning has been installed in both the main house as well as the guest cottage!The SpaceMain house: An open floor plan featuring the kitchen, living room, dining area, and outdoor deck, all with spectacular views of the lagoon. Both bedrooms feature floor-to-ceiling windows that face the water. The primary bedroom has a king bed and the secondary bedroom has two twin beds as well as a crib. The full bathroom includes a bathtub.Guest cottage: A two-bedroom cottage with a Jack & Jill bathroom. One room features a desk, a peloton bike, and a twin bed. The other room has a queen bed. Just s

🛏 4 beds · 👥 7 guests
$314 /night
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Renovated Historic House "The Legacy House" Oak Bluffs, Massachusetts

Renovated Historic House "The Legacy House"

Located in Oak Bluffs, Massachusetts, United States. Renovated Historic House "The Legacy House" 2 Blocks - walking distance to Inkwell Beach! Walking distance to Circuit Avenue, Ocean Park, and Oak Bluffs ferry. Peaceful, tranquil, historic neighborhood within walking distance of all the attractions of Oak Bluffs. Lovely home and available for Summer and Autumn 2022. New state-of-the-art kitchen and modern bathroom upgrades. Unique space with so much personality. Large front sitting/family room, dining room, and 5 bedrooms. Wrap-around porch and ample off-street private parking. Great layout for 2 families. 2 full bathrooms - one on each level. Large rear deck with outdoor shower. 2 blocks from the tennis, pickleball, and basketball courts. Perfect location to enjoy sunrise and walk to the polar bears in the early AM. Bedrooms:Bedroom 1: King Bed (upstairs)- Large room, ceiling fan, lots of windows and space, flat screen with cableBedroom 2: Queen Bed (upstairs)- Large room, ceiling fan, private 2nd-floor balcony Bedroom 3: Doub

🛏 5 beds · 👥 10 guests
$527 /night
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Location & Charm -- Central AC, 100% Renewable Energy Oak Bluffs, Massachusetts

Location & Charm -- Central AC, 100% Renewable Energy

Located in Oak Bluffs, Massachusetts, United States. Location & Charm -- Central AC, 100% Renewable Energy This home is perfectly located - a short walk to Inkwell Beach, downtown Oak Bluffs, and the OB Ferry. One side of the home is bordered by the Nashawena Park Greenway, which offers a pleasant stroll to the beach and waterfront, while just around the corner you will find tennis and basketball courts, as well as a playground. Inside the home you will find a freshly renovated kitchen, two full bathrooms with modern renovations, central AC, antique hardwood floors, and high efficiency washer/dryer. Outside, there is a large wrap-around farmers porch with gas grill and large outdoor dining table, as well as an adjacent outdoor shower with changing area. You may also want to check out my other listings: 43151 and 43322.Keywords: House

🛏 4 beds · 👥 8 guests
$359 /night
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Oak Bluff's Victorian Walk to Town & Beaches Oak Bluffs, Massachusetts

Oak Bluff's Victorian Walk to Town & Beaches

Located in Oak Bluffs, Massachusetts, United States. Oak Bluff's Victorian Walk to Town & Beaches About this spaceFirst floor has AC and hosts windowed living, dining, work space, kitchen and garden apartment that sleeps 2 and has AC, a private bath and patio.Three 2nd floor bedrooms sleep 7 - each with AC, private bath & balcony.3rd floor sleeps 4 - with AC, living, kitchen, bath & balcony connected to exterior staircase & breezewayThe large veranda has a gas barbecue, dining & seating area overlooking manicured groundsLandscaped yard, picnic area, fire pit, hammock, swings & outdoor showerThe spaceThe home is located a true walking distance to Oak Bluffs Harbor, Beaches, Circuit Avenue Shopping & Dinning, the popular Gingerbread Cottages Community, Historic Ocean Park and steps away from many of the highlight properties on the African-American Heritage Trail of Martha’s Vineyard.This property is a former bed & breakfast and as such is capable of host multiple small groups of guests and families with independent rooms for sleeping and b

🛏 5 beds · 👥 13 guests
$730 /night
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Fully Renovated & Spacious home within walking distance of Oak Bluffs / Beaches Oak Bluffs, Massachusetts

Fully Renovated & Spacious home within walking distance of Oak Bluffs / Beaches

Located in Oak Bluffs, Massachusetts, United States. Fully Renovated & Spacious home within walking distance of Oak Bluffs / Beaches Newly renovated three-level home with three bedrooms and two bathrooms within walking distance to the heart of Downtown Oak Bluffs and beaches. This location allows you to be at the center of activity, from Fourth of July fireworks to Illumination but a quick escape into the quiet neighborhood of The Highlands. Walking distance from Oak Bluffs Town Beach (Inkwell) and ferry station. A bright, spacious, fully renovated, and well-appointed must-see home that you won’t want to leave. Comfortable living spaces for six people to relax and socialize. Open kitchen with new appliances and all the cooking tools necessary to whip up a pot of chowda or to have guests over to enjoy a lobster bake. Beautiful rooftop deck with a view of the Harbor and lake or a great place to listen to the morning chirping of birds. Two Bedrooms on the second floor- one with a comfortable Queen bed and the other with two twin beds. Maste

🛏 3 beds · 👥 6 guests
$318 /night
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Coastal Retreat | Walk to Inkwell Beach, Dining & Flying Horses Carousel Oak Bluffs, Massachusetts

Coastal Retreat | Walk to Inkwell Beach, Dining & Flying Horses Carousel

Located in Oak Bluffs, Massachusetts, United States. Coastal Retreat | Walk to Inkwell Beach, Dining & Flying Horses Carousel Oak Leaf Cape CottageOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located walking distance to the center of Oak Bluffs, this 4BR/2BA home offers a relaxing retreat close to all the action. Stroll to Inkwell Beach or an array of local eateries. Walk to the ferry dock and set off on a scenic day trip to Nantucket.Dine alfresco at a shaded patio table in the yard. You’ll love the charming feel of this warmly decorated home.LIVING AREAThe inviting living area features a variety of seating and a TV.KITCHEN & DININGPrepare tasty meals in the kitchen, outfitted with a full suite of appliances.The dining table seats eight.BED & BATHThis home sleeps eight guests between four bedrooms.The primary bedroom is furnished with a queen bed. The en-suite bathroom has a tub/shower combination. The second bedroom is equipped with a queen bed.

🛏 4 beds · 👥 8 guests
$157 /night
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Sunny 2bedroom condo w pool! Vineyard Haven, Massachusetts

Sunny 2bedroom condo w pool!

Located in Vineyard Haven, Massachusetts, United States. Sunny 2bedroom condo w pool! Two bedroom condo lots of light overlooking Vineyard Haven harbor. Ten minute WALK to the ferry, town, local restaurants and town beach. Outdoor pool on the property for guests. Bright living room with plenty of seating for up to 4 people. Outdoor deck with dining table and view of the water. Water views from deck, living room, and primary bedroom. AC in both bedrooms July 1 - Sept 5. Second floor on exterior stairs. Quiet condo association. One parking spot provided. for non commercial vehicles only. Easy walk to local buses and taxis come to house. No need for a car if u can’t get a ferry reservation.

🛏 2 beds · 👥 4 guests
$178 /night
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Bright old-world cottage with two porches & large yard - walk to town & beaches Oak Bluffs, Massachusetts

Bright old-world cottage with two porches & large yard - walk to town & beaches

Located in Oak Bluffs, Massachusetts, United States. Bright old-world cottage with two porches & large yard - walk to town & beaches Oak Bluffs CottageOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Savor the old-world charms of Oak Bluffs Cottage, an ideally situated Martha's Vineyard getaway with a two-level porch to enjoy quiet island mornings and evenings! Take advantage of the provided beach chairs as you spend fun summer days in the sun and come home from the beach to prepare meals for the whole family in the full kitchen, or opt for an outdoor barbecue with the provided grill, the spacious yard, and the shaded deck. Don't worry about the heat, as there are new ductless mini-split air-conditioning units in the common areas and all three bedrooms.What's nearby: This home is conveniently located on the edge of downtown Oak Bluffs, just over half a mile west of the ferry terminal. You'll be within easy walking distance of great restaurants, a marke

🛏 3 beds · 👥 6 guests
$269 /night
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Coastal Farmhouse With Connected Carriage House Oak Bluffs, Massachusetts

Coastal Farmhouse With Connected Carriage House

Located in Oak Bluffs, Massachusetts, United States. Coastal Farmhouse With Connected Carriage House POINT B EXCLUSIVE - This newly built Farmhouse with Connected Carriage House features a modern coastal-style with nice indoor and outdoor living space, is conveniently located near downtown Oak Bluffs, but tucked away in a quieter neighborhood.The property features a four-bedroom Main House with a connected one-bedroom Carriage House suite with its own entrance. The first floor of the Main House features an open layout with Living, Dining and Kitchen Areas. The hip coastal-vibe has combinations of white and natural wood, with subtle use of blues, greys and some other subdued colors. The Living Area has fireplace, large screen TV, built-ins, plus sofa and chair seating.The Dining Area sits between the Living Area and Kitchen. It is framed by a sliding glass door that opens to the large back patio for outdoor dining. The Chef Kitchen has a center prep island/breakfast bar, stainless appliances, farmer's sink, and white quartz counters.The P

🛏 5 beds · 👥 10 guests
$718 /night
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Charming, Dog-Friendly House with Lots of Entertainment & Gourmet Kitchen Oak Bluffs, Massachusetts

Charming, Dog-Friendly House with Lots of Entertainment & Gourmet Kitchen

Located in Oak Bluffs, Massachusetts, United States. Charming, Dog-Friendly House with Lots of Entertainment & Gourmet Kitchen Bright GroveOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This charming Oak Bluffs vacation rental is the perfect choice for a group that wants something a bit upscale. With tons of entertainment options and a gorgeous gourmet kitchen, this home away from home has something for everyone. With light walls, hardwood floors, and high ceilings, the living room feels refined and welcoming. A selection of books and board games is available, so whether you feel sociable or not, you've got options. Settle into the couch and watch something on cable or a DVD, or pick something off Netflix. If you're feeling mellow, put some music over the stereo and have a chat with your friends, or log onto the WiFi to find an ambitious recipe to make for dinner. Boasting granite counters and stainless steel appliances, the gourmet kitchen is as bea

🛏 3 beds · 👥 6 guests
$246 /night
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Large, Charming Vintage Cape Cod Cottage, 2 Blocks to Town and Beaches! Oak Bluffs, Massachusetts

Large, Charming Vintage Cape Cod Cottage, 2 Blocks to Town and Beaches!

Located in Oak Bluffs, Massachusetts, United States. Large, Charming Vintage Cape Cod Cottage, 2 Blocks to Town and Beaches! Victorian Cape Cod Cottage located in the highly desired Oak Bluffs Copeland District in Martha's Vineyard. Large family home, with a great porch and eat-in-kitchen! Sleeps 10. Two blocks walking distance to downtown Oak Bluffs and beaches. Walking distance to Oak Bluffs center, gingerbread cottages, OB harbor, Steamship Authority ferry, restaurants and more.... Off-street parking, Wireless Internet and Cable TV.

🛏 5 beds · 👥 10 guests
$513 /night
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Dog-friendly home with fenced yard- walking distance to beach, ferry & town Oak Bluffs, Massachusetts

Dog-friendly home with fenced yard- walking distance to beach, ferry & town

Located in Oak Bluffs, Massachusetts, United States. Dog-friendly home with fenced yard- walking distance to beach, ferry & town Wayland VictorianOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Enjoy one of the most enviable locations on Martha's Vineyard when you stay at this four-bedroom Oak Bluffs home, a beautifully renovated Victorian with a fenced yard, a porch and deck with accommodations for up to 10 guests.Perfectly situated within half a mile of downtown Oak Bluffs and the ferry terminal, this two-level home is just a short walk from fantastic restaurants, shops, beaches, bicycle and moped rental stores, and nightlife. You'll be two blocks from the edge of the Oak Bluffs Harbor and only half a mile from East Chop and Oak Bluffs Town Beaches.An ideal destination for family vacations, this home seamlessly blends its Victorian character with modern amenities to make guests feel right at home.The first floor was recently renovated to create a br

🛏 4 beds · 👥 10 guests
$426 /night
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Vacation In This Historic And Luxurious Martha's Vineyard Home Oak Bluffs, Massachusetts

Vacation In This Historic And Luxurious Martha's Vineyard Home

Located in Oak Bluffs, Massachusetts, United States. Vacation In This Historic And Luxurious Martha's Vineyard Home Perched on the corner of Ocean Park overlooking Nantucket Sound and across the street from the beach, this elegant home in Oak Bluffs historic Copeland District is one of the premiere houses on Martha's Vineyard. Wide porches surround three sides of the house. A glass enclosed porch with antique wicker swings is the perfect spot to enjoy band concerts in the gazebo, view the annual August fireworks display, or simply enjoy the ocean across the street. A side porch with a large teak table invites grilling and al fresco dining, while another porch offers a table for breakfast or lunch and plush arm chairs for watching the sun rise, reading, napping, or enjoying an unobstructed view of the Atlantic Ocean and the horizon. Across the street from the beach and a five minute walk to the town of Oak Bluffs, the Flying Horses Carousel, and the ferry terminal, this home is perfectly situated. In addition to six light-filled, airy

🛏 7 beds · 👥 14 guests
$1,632 /night
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Amazing Gem with Guest House and Private Sandy Beach on Lagoon Pond Oak Bluffs, Massachusetts

Amazing Gem with Guest House and Private Sandy Beach on Lagoon Pond

Located in Oak Bluffs, Massachusetts, United States. Amazing Gem with Guest House and Private Sandy Beach on Lagoon Pond Nestled on a quiet road within walking distance to Oak Bluffs, this 3-bedroom house with a separate 1-bedroom guest house offers a light-filled, peaceful retreat with amazing Lagoon access for up to ten guests. Featured on HBO Max’s “Beach Cottage Chronicles” Season 3, Episode 10 -- The Lagoon House. See more at marthasvineyard-retreat.comBeautifully renovated and superbly decorated, this home balances tasteful elegance and modern comfort. Exquisite stone patio opens to terraced steps leading to 130 feet of private, sandy beach on the Lagoon.Beach Access! Extraordinary 137 feet of private, sandy beach on the Lagoon Pond just steps (48 steps to be precise) from your door. The Lagoon is warmer and calmer than the ocean, making it perfect for swimming (especially for little ones). Spending a day at South Beach, the Inkwell or Jaws Bridge is certainly not to be missed or minimized. But with a sandy beach and beautiful wat

🛏 5 beds · 👥 10 guests
$874 /night
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Dog-Friendly Home w/Amazing Fenced-In Yards, Private Washer/Dryer, Free WiFi Oak Bluffs, Massachusetts

Dog-Friendly Home w/Amazing Fenced-In Yards, Private Washer/Dryer, Free WiFi

Located in Oak Bluffs, Massachusetts, United States. Dog-Friendly Home w/Amazing Fenced-In Yards, Private Washer/Dryer, Free WiFi Farmhouse FantasyOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This lovely three-bedroom home has plenty of 19th-century farmhouse charm, ideal for your next vacation to Oak Bluffs. Downstairs, the main-level living area boasts an open floor plan, lustrous wood floors, and a bright and welcoming atmosphere, with cascades of natural light entering through large windows on all sides. The full kitchen includes all the small and major appliances and counter space the family chef will need to prepare delightful meals, which you can enjoy on the dining table with seating for four or outside as an al-fresco meal. The living area features handsome furniture, a decorative fireplace, and a large flatscreen TV for those fun family movie nights. Through picturesque French doors, you'll find an enclosed, furnished yard with an attract

🛏 3 beds · 👥 6 guests
$734 /night
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Sweet Apartment in the Heart of Oak Bluffs Oak Bluffs, Massachusetts

Sweet Apartment in the Heart of Oak Bluffs

Located in Oak Bluffs, Massachusetts, United States. Sweet Apartment in the Heart of Oak Bluffs This charming apartment is centrally located on Circuit Ave in the heart of Oak Bluffs above a popular restaurant. It is steps away from the harbor, the historic Inkwell Beach and Flying Horses Carousel as well as the Oak Bluffs Steamship Authority. . There is one bedroom with a queen bed and a common room that has a pull out sofa. It has a full kitchen as well as a washer and dryer. There are wood floors throughout .*Due to COVID 19 the entrance is shared with a busy restaurant that has seating on the deck right outside the windows of the apartment. There are privacy curtains but it can be busy and loud*

🛏 2 beds · 👥 4 guests
$533 /night
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Discount! September Weeks Available! -6 Bedroom Oak Bluffs Victorian. Oak Bluffs, Massachusetts

Discount! September Weeks Available! -6 Bedroom Oak Bluffs Victorian.

Located in Oak Bluffs, Massachusetts, United States. Discount! September Weeks Available! -6 Bedroom Oak Bluffs Victorian. SEPTEMBER WEEKS STILL AVAILABLE. Become a Friend of 20 Samoset! First year on VRBO. 6 Bedrooms will comfortably allow your family to vacation in Oak Bluffs. A classic Victorian jewel, the house at 30 Samoset was built in 1874 and is typical of the Queen Anne style. It is large and asymmetric with a wrap-around porch. The east side also has a small deck off the kitchen (this is very nice for breakfast). On the west side there is a stoop off the kitchen and a stoop from the shower room, both opening to a fenced yard with a nice brick terrace with table and chairs. This side also has a hedged yard with a gate closing it from the street. The east side has off street parking space for two cars. The location of the home allows an easy walk to the beach and walking distance to the Oak Bluffs Reliable grocery store, restaurants and shops. Families will enjoy walking along Ocean Park to the historic Flying Horses Car

🛏 6 beds · 👥 12 guests
$334 /night
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Your "Vineyard Dream" Vacation - OAK BLUFFS -Sunny Open Floor Plan Close to Town Oak Bluffs, Massachusetts

Your "Vineyard Dream" Vacation - OAK BLUFFS -Sunny Open Floor Plan Close to Town

Located in Oak Bluffs, Massachusetts, United States. Your "Vineyard Dream" Vacation - OAK BLUFFS -Sunny Open Floor Plan Close to Town A BEAUTIFUL PROPERTY CLOSE TO TOWN-GREAT PRICE! LOTS OF PRIVACY BUT CLOSE TO EVERYTHING IN OB.ONE WEEK MINIMUM FOR ALL PEAK SEASON RENTALS (JULY - LABOR DAY)**PLEASE NOTE BEFORE BOOKING: WE DO NOT SUPPLY SHEETS OR TOWELS. All beds have comforters, blankets and pillows**Life is a dream on Dreamer's Way - This very clean, comfortable, updated home with an open concept layout and plenty of windows for sunlight is located on a quiet, private street close to the fun of Circuit Ave. (10-15 minute walk). Please read our reviews to find out why guests say our house is the perfect gathering place for family and friends. Tastefully decorated rooms, a spacious deck with wrap around bench and dining table, chairs are adjacent to a wonderfully spacious, custom outdoor shower w/changing area are a few of our guests' top favorite things about the house. The kitchen is convenient to the back deck via sliding doors that

🛏 4 beds · 👥 8 guests
$305 /night
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Inviting, two-story home with a large yard, sunroom, balcony, & washer/dryer

Oak Bluffs, Massachusetts

Inviting, two-story home with a large yard, sunroom, balcony, & washer/dryer

🛏 3 bed · 👥 8 guests

Located in Oak Bluffs, Massachusetts, United States. Inviting, two-story home with a large yard, sunroom, balcony, & washer/dryer Gingerbread DreamOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Experience the laidback lifestyle of the Vineyard from this classic, two-story Oak Bluffs vacation rental! Located just a short walk from downtown and the ferry, this home is ideal for those seeking easy access to the coast, local beaches, and an abundance of other family-friendly attractions. Enjoy a leisurely bike ride, check out the Flying Horses Carousel (the oldest platform carousel in the country!), then spend your afternoon swimming in the warm waters of Nantucket Sound. Or, venture to Joseph Sylvia State Beach, ideal for beachcombing, windsurfing, and fishing for striped bass. Timeless attractions like Martha's Vineyard Performing Arts Center, Flying Horses Carousel, Reliable Market, and Inkwell Beach are all within a three-mile radius. Or check out Ob

$279

/ night

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#CozyBluffs #OakBluffs #EastChop 1 BD, 1.5 bath home-Walk to Town-Ferries-Beach!

Oak Bluffs, Massachusetts

#CozyBluffs #OakBluffs #EastChop 1 BD, 1.5 bath home-Walk to Town-Ferries-Beach!

🛏 1 bed · 👥 2 guests

Located in Oak Bluffs, Massachusetts, United States. #CozyBluffs #OakBluffs #EastChop 1 BD, 1.5 bath home-Walk to Town-Ferries-Beach! Introducing our #CozyBluffs home in Oak Bluffs on Martha's Vineyard! Designed by local Architect Chuck Sullivan and built in 2013 #CozyBluffs is nestled in a quaint, historic Oak Bluffs residential neighborhood and #CozyBluffs is walking distance to Circuit Ave, Hi-Speed and Auto Ferry and town beach!This 755 Sq Ft split level standalone house has one large bedroom with a custom Saatva Cal King bed, ensuite bath and balcony. There is a flex space loft with reading niche, desk/work area so you can work and play! The first floor features an open concept living, kitchen and dining areas & a 1/2 bath. There is a full basement accessed from the living room with washer/dryer/drying rack/iron and ironing board. Private and enclosed outdoor area includes an expansive private backyard with BBQ, dining and seating areas, and outdoor shower. There is a parking area in front of the house. #CozyBluffs is located only

$343

/ night

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Oak Bluffs Family Retreat - Private Roundabout, Walk to the Beach & Downtown OB.

Oak Bluffs, Massachusetts

Oak Bluffs Family Retreat - Private Roundabout, Walk to the Beach & Downtown OB.

🛏 3 bed · 👥 6 guests

Located in Oak Bluffs, Massachusetts, United States. Oak Bluffs Family Retreat - Private Roundabout, Walk to the Beach & Downtown OB. Renovated in 2022, The Panola House is tucked away on a private lot with its own roundabout driveway. Walk to the center of Oak Bluffs and the OB Ferry. (Scenic 15 minute walk brings you to the Historic Campground, right behind the center of Downtown OB, Circuit Avenue .) Inkwell Beach is a short 5-10 minute walk from there, if you don’t stop for ice cream :) Each location above is accessible by bike in 7 minutes and car in less than 10 minutes. The 1st floor has 1,500 sq. ft of living space with an additional 1,500 in the finished lower level, perfect for family time, children, teenagers and adults. There is a 65 inch TV that connects to Sling TV for cable and Netflix. (Media & entertainment, board games, and movies.).The lower level also has a pullout full-sized bed and a 1/2 bathroom in addition to the three bedrooms on the 1st floor. Central A/C throughout the house (installed in 2022). The outdoor

$739

/ night

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Serene home with backyard barbecue area - bike to Arts District, 1 mile to beach

Oak Bluffs, Massachusetts

Serene home with backyard barbecue area - bike to Arts District, 1 mile to beach

🛏 4 bed · 👥 8 guests

Located in Oak Bluffs, Massachusetts, United States. Serene home with backyard barbecue area - bike to Arts District, 1 mile to beach Vineyard HavenOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This charming home on Martha's Vineyard is the perfect destination for your next family getaway. You'll enjoy a huge backyard with a private hedge, a picnic table, and a grill for summer cookouts, along with a private porch and terrace. Inside, you'll find two living rooms with plenty of seating for bonding time and a TV with cable and a DVD player for movie nights.What's Nearby:This home lies on the northeastern shore of Martha's Vineyard, about one mile from Inkwell Beach. You'll be within a short walk or bike ride from the Oak Bluff's Arts District, Circuit Avenue, and numerous restaurants, including Smoke n' Bones BBQ and the fabled Tony's Market.Things to Know:Full kitchen (with dishwasher)If you are bringing a dog on your trip, the pet fee is already in

$255

/ night

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Great location, happy house 0.5 mile Nancy’s & Jetty Beach.

Oak Bluffs, Massachusetts

Great location, happy house 0.5 mile Nancy’s & Jetty Beach.

🛏 3 bed · 👥 8 guests

Located in Oak Bluffs, Massachusetts, United States. Great location, happy house 0.5 mile Nancy’s & Jetty Beach. 1900's Victorian, renovated and newly furnished. House is located on New York Ave, which is the main road between Oak Bluffs and Vineyard Haven. The bus goes past the house every twenty minutes during the summer and can be flagged. House is approximately 1,600 square feet. House purchased in 2018 and all furnishings and furniture is new. Kitchen and down stairs bathroom are newly renovated! First floor includes living room with 50" HDTV, and two large coaches. It is connected to den with sleeper sofa, coffee table, table to play games/puzzles and sitting chair to enjoy a book. Kitchen is eat-in and includes various appliances, including blender, toaster, coffee maker, microwave. Off the kitchen is a bathroom with shower, toilet and sink.Three upstairs bedrooms: 1) master bedroom with small futon, pack and play or air mattress, queen size bed, dresser and side table and closet 2) queen size bed with side table, dresser and

$211

/ night

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COZY 3 BR/2 BA CAPE COD IN QUIET NEIGHBORHOOD. CLOSE TO OB CENTER AND LAGOON.

Oak Bluffs, Massachusetts

COZY 3 BR/2 BA CAPE COD IN QUIET NEIGHBORHOOD. CLOSE TO OB CENTER AND LAGOON.

🛏 3 bed · 👥 6 guests

Located in Oak Bluffs, Massachusetts, United States. COZY 3 BR/2 BA CAPE COD IN QUIET NEIGHBORHOOD. CLOSE TO OB CENTER AND LAGOON. Located in the beautiful Lagoon Heights neighborhood, you'll enjoy this lovely 3 Bedroom, 2 Bath cozy Cape Cod home with a finished basement within walking distance of Oak Bluffs Center and the Lagoon at the end of the road. The house has been renovated with a new kitchen and new bathrooms and beautifully decorated with all new furniture, etc.This desirable location includes a first-floor primary bedroom with a Queen size bed and two bedrooms with two twins each (which can be converted to King beds) on the second floor. The partially finished basement provides additional living space for the family to enjoy and a dedicated remote work space. The kitchen is the perfect space for gathering after a fun filled day at any of the beautiful beaches on Martha's Vineyard. There is a newly renovated deck off the kitchen that is just right for grilling and enjoying a cocktail.The home is centrally located within a few m

$464

/ night

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Private Beach Waterfront Oak-Bluffs Family Cottage

Oak Bluffs, Massachusetts

Private Beach Waterfront Oak-Bluffs Family Cottage

🛏 4 bed · 👥 7 guests

Located in Oak Bluffs, Massachusetts, United States. Private Beach Waterfront Oak-Bluffs Family Cottage Experience the magic of Martha's Vineyard from our beachfront retreat. Nestled in a quiet neighborhood, yet conveniently close to Oak Bluffs, you'll find the perfect balance of seclusion and accessibility. Wake up to stunning views of the Lagoon and end your day with unparalleled sunsets reflecting off of the still water. *2024 Season Update - Air conditioning has been installed in both the main house as well as the guest cottage!The SpaceMain house: An open floor plan featuring the kitchen, living room, dining area, and outdoor deck, all with spectacular views of the lagoon. Both bedrooms feature floor-to-ceiling windows that face the water. The primary bedroom has a king bed and the secondary bedroom has two twin beds as well as a crib. The full bathroom includes a bathtub.Guest cottage: A two-bedroom cottage with a Jack & Jill bathroom. One room features a desk, a peloton bike, and a twin bed. The other room has a queen bed. Just s

$314

/ night

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Renovated Historic House "The Legacy House"

Oak Bluffs, Massachusetts

Renovated Historic House "The Legacy House"

🛏 5 bed · 👥 10 guests

Located in Oak Bluffs, Massachusetts, United States. Renovated Historic House "The Legacy House" 2 Blocks - walking distance to Inkwell Beach! Walking distance to Circuit Avenue, Ocean Park, and Oak Bluffs ferry. Peaceful, tranquil, historic neighborhood within walking distance of all the attractions of Oak Bluffs. Lovely home and available for Summer and Autumn 2022. New state-of-the-art kitchen and modern bathroom upgrades. Unique space with so much personality. Large front sitting/family room, dining room, and 5 bedrooms. Wrap-around porch and ample off-street private parking. Great layout for 2 families. 2 full bathrooms - one on each level. Large rear deck with outdoor shower. 2 blocks from the tennis, pickleball, and basketball courts. Perfect location to enjoy sunrise and walk to the polar bears in the early AM. Bedrooms:Bedroom 1: King Bed (upstairs)- Large room, ceiling fan, lots of windows and space, flat screen with cableBedroom 2: Queen Bed (upstairs)- Large room, ceiling fan, private 2nd-floor balcony Bedroom 3: Doub

$527

/ night

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Location & Charm -- Central AC, 100% Renewable Energy

Oak Bluffs, Massachusetts

Location & Charm -- Central AC, 100% Renewable Energy

🛏 4 bed · 👥 8 guests

Located in Oak Bluffs, Massachusetts, United States. Location & Charm -- Central AC, 100% Renewable Energy This home is perfectly located - a short walk to Inkwell Beach, downtown Oak Bluffs, and the OB Ferry. One side of the home is bordered by the Nashawena Park Greenway, which offers a pleasant stroll to the beach and waterfront, while just around the corner you will find tennis and basketball courts, as well as a playground. Inside the home you will find a freshly renovated kitchen, two full bathrooms with modern renovations, central AC, antique hardwood floors, and high efficiency washer/dryer. Outside, there is a large wrap-around farmers porch with gas grill and large outdoor dining table, as well as an adjacent outdoor shower with changing area. You may also want to check out my other listings: 43151 and 43322.Keywords: House

$359

/ night

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Oak Bluff's Victorian Walk to Town & Beaches

Oak Bluffs, Massachusetts

Oak Bluff's Victorian Walk to Town & Beaches

🛏 5 bed · 👥 13 guests

Located in Oak Bluffs, Massachusetts, United States. Oak Bluff's Victorian Walk to Town & Beaches About this spaceFirst floor has AC and hosts windowed living, dining, work space, kitchen and garden apartment that sleeps 2 and has AC, a private bath and patio.Three 2nd floor bedrooms sleep 7 - each with AC, private bath & balcony.3rd floor sleeps 4 - with AC, living, kitchen, bath & balcony connected to exterior staircase & breezewayThe large veranda has a gas barbecue, dining & seating area overlooking manicured groundsLandscaped yard, picnic area, fire pit, hammock, swings & outdoor showerThe spaceThe home is located a true walking distance to Oak Bluffs Harbor, Beaches, Circuit Avenue Shopping & Dinning, the popular Gingerbread Cottages Community, Historic Ocean Park and steps away from many of the highlight properties on the African-American Heritage Trail of Martha’s Vineyard.This property is a former bed & breakfast and as such is capable of host multiple small groups of guests and families with independent rooms for sleeping and b

$730

/ night

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Fully Renovated & Spacious home within walking distance of Oak Bluffs / Beaches

Oak Bluffs, Massachusetts

Fully Renovated & Spacious home within walking distance of Oak Bluffs / Beaches

🛏 3 bed · 👥 6 guests

Located in Oak Bluffs, Massachusetts, United States. Fully Renovated & Spacious home within walking distance of Oak Bluffs / Beaches Newly renovated three-level home with three bedrooms and two bathrooms within walking distance to the heart of Downtown Oak Bluffs and beaches. This location allows you to be at the center of activity, from Fourth of July fireworks to Illumination but a quick escape into the quiet neighborhood of The Highlands. Walking distance from Oak Bluffs Town Beach (Inkwell) and ferry station. A bright, spacious, fully renovated, and well-appointed must-see home that you won’t want to leave. Comfortable living spaces for six people to relax and socialize. Open kitchen with new appliances and all the cooking tools necessary to whip up a pot of chowda or to have guests over to enjoy a lobster bake. Beautiful rooftop deck with a view of the Harbor and lake or a great place to listen to the morning chirping of birds. Two Bedrooms on the second floor- one with a comfortable Queen bed and the other with two twin beds. Maste

$318

/ night

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Coastal Retreat | Walk to Inkwell Beach, Dining & Flying Horses Carousel

Oak Bluffs, Massachusetts

Coastal Retreat | Walk to Inkwell Beach, Dining & Flying Horses Carousel

🛏 4 bed · 👥 8 guests

Located in Oak Bluffs, Massachusetts, United States. Coastal Retreat | Walk to Inkwell Beach, Dining & Flying Horses Carousel Oak Leaf Cape CottageOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located walking distance to the center of Oak Bluffs, this 4BR/2BA home offers a relaxing retreat close to all the action. Stroll to Inkwell Beach or an array of local eateries. Walk to the ferry dock and set off on a scenic day trip to Nantucket.Dine alfresco at a shaded patio table in the yard. You’ll love the charming feel of this warmly decorated home.LIVING AREAThe inviting living area features a variety of seating and a TV.KITCHEN & DININGPrepare tasty meals in the kitchen, outfitted with a full suite of appliances.The dining table seats eight.BED & BATHThis home sleeps eight guests between four bedrooms.The primary bedroom is furnished with a queen bed. The en-suite bathroom has a tub/shower combination. The second bedroom is equipped with a queen bed.

$157

/ night

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Sunny 2bedroom condo w pool!

Vineyard Haven, Massachusetts

Sunny 2bedroom condo w pool!

🛏 2 bed · 👥 4 guests

Located in Vineyard Haven, Massachusetts, United States. Sunny 2bedroom condo w pool! Two bedroom condo lots of light overlooking Vineyard Haven harbor. Ten minute WALK to the ferry, town, local restaurants and town beach. Outdoor pool on the property for guests. Bright living room with plenty of seating for up to 4 people. Outdoor deck with dining table and view of the water. Water views from deck, living room, and primary bedroom. AC in both bedrooms July 1 - Sept 5. Second floor on exterior stairs. Quiet condo association. One parking spot provided. for non commercial vehicles only. Easy walk to local buses and taxis come to house. No need for a car if u can’t get a ferry reservation.

$178

/ night

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Bright old-world cottage with two porches & large yard - walk to town & beaches

Oak Bluffs, Massachusetts

Bright old-world cottage with two porches & large yard - walk to town & beaches

🛏 3 bed · 👥 6 guests

Located in Oak Bluffs, Massachusetts, United States. Bright old-world cottage with two porches & large yard - walk to town & beaches Oak Bluffs CottageOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Savor the old-world charms of Oak Bluffs Cottage, an ideally situated Martha's Vineyard getaway with a two-level porch to enjoy quiet island mornings and evenings! Take advantage of the provided beach chairs as you spend fun summer days in the sun and come home from the beach to prepare meals for the whole family in the full kitchen, or opt for an outdoor barbecue with the provided grill, the spacious yard, and the shaded deck. Don't worry about the heat, as there are new ductless mini-split air-conditioning units in the common areas and all three bedrooms.What's nearby: This home is conveniently located on the edge of downtown Oak Bluffs, just over half a mile west of the ferry terminal. You'll be within easy walking distance of great restaurants, a marke

$269

/ night

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Coastal Farmhouse With Connected Carriage House

Oak Bluffs, Massachusetts

Coastal Farmhouse With Connected Carriage House

🛏 5 bed · 👥 10 guests

Located in Oak Bluffs, Massachusetts, United States. Coastal Farmhouse With Connected Carriage House POINT B EXCLUSIVE - This newly built Farmhouse with Connected Carriage House features a modern coastal-style with nice indoor and outdoor living space, is conveniently located near downtown Oak Bluffs, but tucked away in a quieter neighborhood.The property features a four-bedroom Main House with a connected one-bedroom Carriage House suite with its own entrance. The first floor of the Main House features an open layout with Living, Dining and Kitchen Areas. The hip coastal-vibe has combinations of white and natural wood, with subtle use of blues, greys and some other subdued colors. The Living Area has fireplace, large screen TV, built-ins, plus sofa and chair seating.The Dining Area sits between the Living Area and Kitchen. It is framed by a sliding glass door that opens to the large back patio for outdoor dining. The Chef Kitchen has a center prep island/breakfast bar, stainless appliances, farmer's sink, and white quartz counters.The P

$718

/ night

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Charming, Dog-Friendly House with Lots of Entertainment & Gourmet Kitchen

Oak Bluffs, Massachusetts

Charming, Dog-Friendly House with Lots of Entertainment & Gourmet Kitchen

🛏 3 bed · 👥 6 guests

Located in Oak Bluffs, Massachusetts, United States. Charming, Dog-Friendly House with Lots of Entertainment & Gourmet Kitchen Bright GroveOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This charming Oak Bluffs vacation rental is the perfect choice for a group that wants something a bit upscale. With tons of entertainment options and a gorgeous gourmet kitchen, this home away from home has something for everyone. With light walls, hardwood floors, and high ceilings, the living room feels refined and welcoming. A selection of books and board games is available, so whether you feel sociable or not, you've got options. Settle into the couch and watch something on cable or a DVD, or pick something off Netflix. If you're feeling mellow, put some music over the stereo and have a chat with your friends, or log onto the WiFi to find an ambitious recipe to make for dinner. Boasting granite counters and stainless steel appliances, the gourmet kitchen is as bea

$246

/ night

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Large, Charming Vintage Cape Cod Cottage, 2 Blocks to Town and Beaches!

Oak Bluffs, Massachusetts

Large, Charming Vintage Cape Cod Cottage, 2 Blocks to Town and Beaches!

🛏 5 bed · 👥 10 guests

Located in Oak Bluffs, Massachusetts, United States. Large, Charming Vintage Cape Cod Cottage, 2 Blocks to Town and Beaches! Victorian Cape Cod Cottage located in the highly desired Oak Bluffs Copeland District in Martha's Vineyard. Large family home, with a great porch and eat-in-kitchen! Sleeps 10. Two blocks walking distance to downtown Oak Bluffs and beaches. Walking distance to Oak Bluffs center, gingerbread cottages, OB harbor, Steamship Authority ferry, restaurants and more.... Off-street parking, Wireless Internet and Cable TV.

$513

/ night

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Dog-friendly home with fenced yard- walking distance to beach, ferry & town

Oak Bluffs, Massachusetts

Dog-friendly home with fenced yard- walking distance to beach, ferry & town

🛏 4 bed · 👥 10 guests

Located in Oak Bluffs, Massachusetts, United States. Dog-friendly home with fenced yard- walking distance to beach, ferry & town Wayland VictorianOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Enjoy one of the most enviable locations on Martha's Vineyard when you stay at this four-bedroom Oak Bluffs home, a beautifully renovated Victorian with a fenced yard, a porch and deck with accommodations for up to 10 guests.Perfectly situated within half a mile of downtown Oak Bluffs and the ferry terminal, this two-level home is just a short walk from fantastic restaurants, shops, beaches, bicycle and moped rental stores, and nightlife. You'll be two blocks from the edge of the Oak Bluffs Harbor and only half a mile from East Chop and Oak Bluffs Town Beaches.An ideal destination for family vacations, this home seamlessly blends its Victorian character with modern amenities to make guests feel right at home.The first floor was recently renovated to create a br

$426

/ night

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Vacation In This Historic And Luxurious Martha's Vineyard Home

Oak Bluffs, Massachusetts

Vacation In This Historic And Luxurious Martha's Vineyard Home

🛏 7 bed · 👥 14 guests

Located in Oak Bluffs, Massachusetts, United States. Vacation In This Historic And Luxurious Martha's Vineyard Home Perched on the corner of Ocean Park overlooking Nantucket Sound and across the street from the beach, this elegant home in Oak Bluffs historic Copeland District is one of the premiere houses on Martha's Vineyard. Wide porches surround three sides of the house. A glass enclosed porch with antique wicker swings is the perfect spot to enjoy band concerts in the gazebo, view the annual August fireworks display, or simply enjoy the ocean across the street. A side porch with a large teak table invites grilling and al fresco dining, while another porch offers a table for breakfast or lunch and plush arm chairs for watching the sun rise, reading, napping, or enjoying an unobstructed view of the Atlantic Ocean and the horizon. Across the street from the beach and a five minute walk to the town of Oak Bluffs, the Flying Horses Carousel, and the ferry terminal, this home is perfectly situated. In addition to six light-filled, airy

$1,632

/ night

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Amazing Gem with Guest House and Private Sandy Beach on Lagoon Pond

Oak Bluffs, Massachusetts

Amazing Gem with Guest House and Private Sandy Beach on Lagoon Pond

🛏 5 bed · 👥 10 guests

Located in Oak Bluffs, Massachusetts, United States. Amazing Gem with Guest House and Private Sandy Beach on Lagoon Pond Nestled on a quiet road within walking distance to Oak Bluffs, this 3-bedroom house with a separate 1-bedroom guest house offers a light-filled, peaceful retreat with amazing Lagoon access for up to ten guests. Featured on HBO Max’s “Beach Cottage Chronicles” Season 3, Episode 10 -- The Lagoon House. See more at marthasvineyard-retreat.comBeautifully renovated and superbly decorated, this home balances tasteful elegance and modern comfort. Exquisite stone patio opens to terraced steps leading to 130 feet of private, sandy beach on the Lagoon.Beach Access! Extraordinary 137 feet of private, sandy beach on the Lagoon Pond just steps (48 steps to be precise) from your door. The Lagoon is warmer and calmer than the ocean, making it perfect for swimming (especially for little ones). Spending a day at South Beach, the Inkwell or Jaws Bridge is certainly not to be missed or minimized. But with a sandy beach and beautiful wat

$874

/ night

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Dog-Friendly Home w/Amazing Fenced-In Yards, Private Washer/Dryer, Free WiFi

Oak Bluffs, Massachusetts

Dog-Friendly Home w/Amazing Fenced-In Yards, Private Washer/Dryer, Free WiFi

🛏 3 bed · 👥 6 guests

Located in Oak Bluffs, Massachusetts, United States. Dog-Friendly Home w/Amazing Fenced-In Yards, Private Washer/Dryer, Free WiFi Farmhouse FantasyOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This lovely three-bedroom home has plenty of 19th-century farmhouse charm, ideal for your next vacation to Oak Bluffs. Downstairs, the main-level living area boasts an open floor plan, lustrous wood floors, and a bright and welcoming atmosphere, with cascades of natural light entering through large windows on all sides. The full kitchen includes all the small and major appliances and counter space the family chef will need to prepare delightful meals, which you can enjoy on the dining table with seating for four or outside as an al-fresco meal. The living area features handsome furniture, a decorative fireplace, and a large flatscreen TV for those fun family movie nights. Through picturesque French doors, you'll find an enclosed, furnished yard with an attract

$734

/ night

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Sweet Apartment in the Heart of Oak Bluffs

Oak Bluffs, Massachusetts

Sweet Apartment in the Heart of Oak Bluffs

🛏 2 bed · 👥 4 guests

Located in Oak Bluffs, Massachusetts, United States. Sweet Apartment in the Heart of Oak Bluffs This charming apartment is centrally located on Circuit Ave in the heart of Oak Bluffs above a popular restaurant. It is steps away from the harbor, the historic Inkwell Beach and Flying Horses Carousel as well as the Oak Bluffs Steamship Authority. . There is one bedroom with a queen bed and a common room that has a pull out sofa. It has a full kitchen as well as a washer and dryer. There are wood floors throughout .*Due to COVID 19 the entrance is shared with a busy restaurant that has seating on the deck right outside the windows of the apartment. There are privacy curtains but it can be busy and loud*

$533

/ night

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Discount! September Weeks Available! -6 Bedroom Oak Bluffs Victorian.

Oak Bluffs, Massachusetts

Discount! September Weeks Available! -6 Bedroom Oak Bluffs Victorian.

🛏 6 bed · 👥 12 guests

Located in Oak Bluffs, Massachusetts, United States. Discount! September Weeks Available! -6 Bedroom Oak Bluffs Victorian. SEPTEMBER WEEKS STILL AVAILABLE. Become a Friend of 20 Samoset! First year on VRBO. 6 Bedrooms will comfortably allow your family to vacation in Oak Bluffs. A classic Victorian jewel, the house at 30 Samoset was built in 1874 and is typical of the Queen Anne style. It is large and asymmetric with a wrap-around porch. The east side also has a small deck off the kitchen (this is very nice for breakfast). On the west side there is a stoop off the kitchen and a stoop from the shower room, both opening to a fenced yard with a nice brick terrace with table and chairs. This side also has a hedged yard with a gate closing it from the street. The east side has off street parking space for two cars. The location of the home allows an easy walk to the beach and walking distance to the Oak Bluffs Reliable grocery store, restaurants and shops. Families will enjoy walking along Ocean Park to the historic Flying Horses Car

$334

/ night

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Your "Vineyard Dream" Vacation - OAK BLUFFS -Sunny Open Floor Plan Close to Town

Oak Bluffs, Massachusetts

Your "Vineyard Dream" Vacation - OAK BLUFFS -Sunny Open Floor Plan Close to Town

🛏 4 bed · 👥 8 guests

Located in Oak Bluffs, Massachusetts, United States. Your "Vineyard Dream" Vacation - OAK BLUFFS -Sunny Open Floor Plan Close to Town A BEAUTIFUL PROPERTY CLOSE TO TOWN-GREAT PRICE! LOTS OF PRIVACY BUT CLOSE TO EVERYTHING IN OB.ONE WEEK MINIMUM FOR ALL PEAK SEASON RENTALS (JULY - LABOR DAY)**PLEASE NOTE BEFORE BOOKING: WE DO NOT SUPPLY SHEETS OR TOWELS. All beds have comforters, blankets and pillows**Life is a dream on Dreamer's Way - This very clean, comfortable, updated home with an open concept layout and plenty of windows for sunlight is located on a quiet, private street close to the fun of Circuit Ave. (10-15 minute walk). Please read our reviews to find out why guests say our house is the perfect gathering place for family and friends. Tastefully decorated rooms, a spacious deck with wrap around bench and dining table, chairs are adjacent to a wonderfully spacious, custom outdoor shower w/changing area are a few of our guests' top favorite things about the house. The kitchen is convenient to the back deck via sliding doors that

$305

/ night

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Inviting, two-story home with a large yard, sunroom, balcony, & washer/dryer

Oak Bluffs, Massachusetts

$279/night

#CozyBluffs #OakBluffs #EastChop 1 BD, 1.5 bath home-Walk to Town-Ferries-Beach!

Oak Bluffs, Massachusetts

$343/night

Oak Bluffs Family Retreat - Private Roundabout, Walk to the Beach & Downtown OB.

Oak Bluffs, Massachusetts

$739/night

Serene home with backyard barbecue area - bike to Arts District, 1 mile to beach

Oak Bluffs, Massachusetts

$255/night

Great location, happy house 0.5 mile Nancy’s & Jetty Beach.

Oak Bluffs, Massachusetts

$211/night

COZY 3 BR/2 BA CAPE COD IN QUIET NEIGHBORHOOD. CLOSE TO OB CENTER AND LAGOON.

Oak Bluffs, Massachusetts

$464/night

Private Beach Waterfront Oak-Bluffs Family Cottage

Oak Bluffs, Massachusetts

$314/night

Renovated Historic House "The Legacy House"

Oak Bluffs, Massachusetts

$527/night

Location & Charm -- Central AC, 100% Renewable Energy

Oak Bluffs, Massachusetts

$359/night

Oak Bluff's Victorian Walk to Town & Beaches

Oak Bluffs, Massachusetts

$730/night

Fully Renovated & Spacious home within walking distance of Oak Bluffs / Beaches

Oak Bluffs, Massachusetts

$318/night

Coastal Retreat | Walk to Inkwell Beach, Dining & Flying Horses Carousel

Oak Bluffs, Massachusetts

$157/night

Sunny 2bedroom condo w pool!

Vineyard Haven, Massachusetts

$178/night

Bright old-world cottage with two porches & large yard - walk to town & beaches

Oak Bluffs, Massachusetts

$269/night

Coastal Farmhouse With Connected Carriage House

Oak Bluffs, Massachusetts

$718/night

Charming, Dog-Friendly House with Lots of Entertainment & Gourmet Kitchen

Oak Bluffs, Massachusetts

$246/night

Large, Charming Vintage Cape Cod Cottage, 2 Blocks to Town and Beaches!

Oak Bluffs, Massachusetts

$513/night

Dog-friendly home with fenced yard- walking distance to beach, ferry & town

Oak Bluffs, Massachusetts

$426/night

Vacation In This Historic And Luxurious Martha's Vineyard Home

Oak Bluffs, Massachusetts

$1,632/night

Amazing Gem with Guest House and Private Sandy Beach on Lagoon Pond

Oak Bluffs, Massachusetts

$874/night

Dog-Friendly Home w/Amazing Fenced-In Yards, Private Washer/Dryer, Free WiFi

Oak Bluffs, Massachusetts

$734/night

Sweet Apartment in the Heart of Oak Bluffs

Oak Bluffs, Massachusetts

$533/night

Discount! September Weeks Available! -6 Bedroom Oak Bluffs Victorian.

Oak Bluffs, Massachusetts

$334/night

Your "Vineyard Dream" Vacation - OAK BLUFFS -Sunny Open Floor Plan Close to Town

Oak Bluffs, Massachusetts

$305/night