94,639 properties available

Located in Oak Bluffs, Massachusetts, United States. Charming Home with High-Speed WiFi, Washer/Dryer, Furnished Deck, & Gas Grill Casa MarianneOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Gorgeous yet family-friendly, this home is ready to host your group getaway. You'll love the natural wood and stone elements of the home, paired perfectly with crisp white walls and shabby chic decor. The furnished screened-in porch may be your favorite spot during your stay. The spacious kitchen features a double oven, dishwasher, toaster oven, and a spacious breakfast bar with room for both adult and child guests to enjoy a snack. Set your fish out out on the private gas grill if you want an extra sear. If you're coming back from the beach, feel free to rinse off in the outdoor shower before coming inside.The bedrooms of this home are each lovingly decorated, so you'll have no problem relaxing. The first bedroom is just to the right when you walk through the fr

Located in Oak Bluffs, Massachusetts, United States. Historic Home in East Chop Renovated home in East Chop, Oak Bluffs, Martha’s Vineyard. Built in 1863 by my great, great grandfather, the house has the charm of a historical home, but has the modern conveniences for you to enjoy a relaxing vacation on Martha’s Vineyard. The house is located in a quiet wooded area in East Chop, an exclusive area of Oak Bluffs. Just walking distance to downtown Oak Bluffs, the house is conveniently located to Oak Bluffs harbor, jetty beach, great family restaurants, and shopping.This 4 bedroom, 2 full bath house has just received a substantial renovation including a new kitchen with stainless steel appliances, master suite w/private bath, laundry room, new heating and air conditioning, instant hot water heater, new hard wood floors, all new furniture, new beds and bedding, and all freshly painted. The house has a wrap-around enclosed porch to enjoy a rest after a busy day at the beach and a new flag stone patio in back that includes a gas grill and n

Located in Oak Bluffs, Massachusetts, United States. CENTRAL AIR! Quiet East Chop Retreat Walk 2 Town and Beach. GAME ROOM!!! We have converted the room in the garage as a place where our guests can go should you have a rainy day or choose a night in. We will be adding a couple arcade games. If there is room we will do a ring toss and a bar height table and chairs. Just a block from the East Chop Bluffs on a sleepy side street in a quiet wooded setting. There are 2 SEPERATE LIVING ROOMS!! Central AC upstairs and down! Large bright kitchen that accesses a separate dining room, inviting screen porch with dining and sitting areas, and sunny rear deck with lots of backyard privacy. Ocean views can be found in the Turret as well as a clear view of the West Chop Lighthouse in Vineyard Haven. Upstairs are 5 bedrooms (3Q, 1F , 2T guest provide linens, towels and bath mats) and 1.5 baths, downstairs has a full bath as well as an outdoor shower. You are just steps from the Lighthouse, Bluff, and one of the most beautiful walks to downtown (~1

Located in Oak Bluffs, Massachusetts, United States. Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2024! Pirate's Reef is a NEW and beautifully decorated residence that offers 5 spacious bedrooms (2 master suites!) with 4.5 bathrooms, full finished basement with wet bar and combo pool table/table tennis, and accommodates up to 12 guests.This is the PERFECT vacation home for you and your guests. This home is nestled behind the historic Shearer Cottage on a quiet lane in East Chop, located just minutes away from all the charm and activities that Oak Bluffs has to offer. The beach, harbor, and town are all just a pleasant 15 minute walk away, or less than a 5 minute drive/bike ride. Guests will enjoy the private, wooded area of the home's setting, allowing one to truly experience the magic of Vineyard "island living."Each floor features 1 master suite and 1 living room, making it quite comfortable for multiple families, large groups, and entertaining. Pirate’s Reef has custom carpentry, a gas fireplace, central air conditi

Located in Oak Bluffs, Massachusetts, United States. Spacious 5-bedroom house with AC and WiFi in brilliant Oak Bluffs Perched on a grassy hill, this majestic home has sweeping views of Oak Bluffs Harbor and is just minutes from East Chop beach. Stylishly decorated and thoughtfully renovated, this charming property offers modern amenities and is the perfect family retreat. The first floor has living, kitchen and dining areas. The living area, just beyond the front entrance and open covered porch, has couch seating and a decorative stone fireplace. The large eat-in dining room has seating for eight. The kitchen has commercial stainless appliances, butcher block counters, a large island for meal preparation and table that seats four. The first floor also has a laundry room, powder room and queen bedroom with private bathroom. The four remaining bedrooms are located on the second floor. The primary Master bedroom has an ensuite bathroom, sitting area, work area, vaulted ceilings, and a stunning waterview from a private balcony. The second M

Located in Oak Bluffs, Massachusetts, United States. Enchanting bungalow with golf nearby, full kitchen, central AC, & washer/dryer East Chop 90Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to coastal living on the East Chop, a perfect place to bring loved ones for a getaway from the hustle and bustle of everyday life. This renovated home is full of contemporary creature comforts but honors the character and charm of old vineyard living. Rent water equipment to spend your days on the ocean kayaking, paddleboarding, sailing, surfing, and every other waterfront activity imaginable. Bring your golf clubs for world-class greens nearby, and enjoy exquisite walkable neighborhoods full of Martha's Vineyard magic.The architectural style draws one immediately to the wrap-around porch. Upon entering the home, the sparkling vintage fir floors, beadboard wainscoting, and a beautiful place to relax and unwind awaits. Many viewing windows and french doors

Located in Oak Bluffs, Massachusetts, United States. Spectacular Classic Waterfront Cottage 33 Beach captures the essence of Martha's Vineyard. Built around the turn of the century as a stop for the New York Yacht Club, "Station 6" has seen more than a century of waterfront activity. Looking across the harbor at Vineyard Haven and West Chop, you can relax and watch the beautiful sunsets or find a perfect spot entertaining friends and family. The private deep water dock and mooring - perfect for swimming, fishing, kayaking, waterboarding or small powerboats. A one minute walk or swim from Eastville Point Beach, you are perfectly positioned on your waterfront cottage. Centrally located, Vineyard Haven just is across the harbor, 3 minutes by boat, or less than a mile by car; Oak Bluffs is a bit over a mile in the opposite direction. A covered patio overlooks the dock and water, and an enclosed living room on the north side provides a cozy spot to read or chat while watching the waterfront activities. Theres a large fireplace in the middle

Located in Oak Bluffs, Massachusetts, United States. Location, Location, Location- Updated East Chop Year Round Home Oak Bluffs: Located in East Chop! Beautiful year round home steps to Oak Bluffs Harbor, East Chop Beach Club, Jetty Beach and Ferries! This 3 bedroom and 2 bath home has washer/dryer, wifi, cable and new hardwood floors and has been recently renovated. Master bedroom has private deck with slight water view. Large yard, outdoor shower on quiet street. Walking distance to public transit. 1 queen bed, 2 double beds and 1 twin bed. Plenty of storage. Multiple outdoor areas for seating. Seating on front porch with comfy couches and swing. Patio off kitchen for your morning coffee or cocktails. Walking distance to town, ferry, beaches and restaurants. This place is perfect for girls weekend, fishing derby, or your family get together. Close to beautiful biking paths along the water. Owner is very responsive and has added a lot of extra touches to help you enjoy your stay including beach chairs, umbrella, beach wagon

Located in Oak Bluffs, Massachusetts, United States. Wonderful three-story home with lovely decks, firepit, fast WiFi & washer/dryer Brewster HouseOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Come and experience Oak Bluff's beautiful beaches, quaint shops, and cozy restaurants at this three-story home!The exterior of the home boasts new renovations, including a privacy fence surrounding the home with lighting, a conversational floating deck (16x16) in addition to the existing deck, and a lounge set with ample seating and a firepit perfect for gathering with s'mores beneath the stars.On the first floor of this retreat, you'll find two separate living areas–the living area to your left features a baseboard heat unit, a comfortable sectional sofa in front of a wall-mounted flat-screen TV with cable, Netflix, and a DVD player, a chess table, an air purifier, two large ottoman seats that fold out to new twin-sized beds, a space heater, and even a well-e

Located in Oak Bluffs, Massachusetts, United States. Historic, dog-friendly beach view house with fast WiFi, ocean view, & grill Captain Shaw Norris HouseOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Don't miss your chance to book this incredible historic beach view home, originally built in 1859, boasting modern amenities and a to-die-for rooftop deck. The three-story home in East Chop features ocean views and abundant private outdoor space. Choose between beachcombing on the sand or admiring the water from home. Enjoy alfresco meals at the outdoor dining table atop the house. The open kitchen is ideal for cooking as it's completely updated with gorgeous white cabinets, recessed lighting, a farmhouse sink, and high-end stainless steel appliances. The formal dining area provides an all-season option for hosting group dinners. Although the home has undergone renovations for your comfort, it retained its charm by keeping fun elements like the blue har

Located in Oak Bluffs, Massachusetts, United States. Delilah & Joseph Pierce House Travel and Enjoy! Built by international artist, curator, educator, advocate, and diplomat Delilah W. Pierce, and her family in 1962, this cottage has 2 bedrooms, one bathroom for your holiday. The Delilah & Joseph Pierce House is an example of a mid-20th-century cottage and living on Martha's Vineyard Island! Oak Bluffs, at the time, was a community of humble and unpretentious socialites who focused their energy on social and economic justice all year, and strategy and relaxation during the summer with national and international peers. Now you can experience it! Situated near East Chop, this cottage is a 2-minute drive to the Oak Bluffs State Beach. You will enjoy evenings in the backyard and walks through the charming neighborhood! This is a family home with 5 generations of history! Book now! This home additionally has an enclosed porch (with a Queen sized futon), a living room convertible couch (Queen-sized bed), a big yard to play, and steps to public

Located in Vineyard Haven, Massachusetts, United States. Charming, Clean And Well Maintained Home Walking Distance To Town And Beach Enjoy a relaxing vacation in a charming vineyard two bedroom two bathroom home. Located a short walk to downtown Vineyard Haven, Owen Little Way beach, and a quick bike ride (1 Mile) to Tashmoo beach, this house is perfect for a small family or two couples. The home is two levels with both bedrooms and a full bathroom located on the second floor. The bedrooms of equal size offer a California king one and a queen and one single in the other. Bedrooms have pillow top mattresses, ample closet space. All windows in the house were replaced in 2017 and the bedroom windows were doubled in size. Central air conditioning installed in 2023. Downstairs is an open living area with new over-sized sectional sofa (new spring 2022) and two over-sized arm chairs that sit in a light flooded room. There is a 40in LED TV mounted to the wall with cable/DVD and wireless internet. A full bathroom is located downstairs. The open kitc

Located in Oak Bluffs, Massachusetts, United States. Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View. The property is conveniently located near the center of Oak Bluffs and with many great restaurant and out door activity, all within Walking distance from the property.You can also walk to different fast ferry terminals to visit Nantucket, Falmouth or Rhode Island. If you like water sport, you can rent jet ski, paddle board, one of the rental that is located one block away from the property. There is a public fishing pier located directly across from the property or you can go fishing with one of the party boats . Many beautiful beaches on the island can be reached within minutes.

Located in Oak Bluffs, Massachusetts, United States. Charming, cozy spacious home within 1 mile walking distance to Oak Bluffs This home has all the amenities to make your stay a comfortable one. Its character stems from being built in the 1920s with the original staircase and wood in place. You will be able to enjoy a meal with the family in the spacious living room and dining room or outside in the yard. Each bedroom has air conditioning along with . In the evenings spend time in the back yard socializing on the comfortable outdoor seating. The proximity to downtown Oak bluff allows you to walk and get a nice cup of coffee from Mocha Motts and be back before the rest of the family awakens. On Bus line #13 and #9. SATURDAY CHECK-In June-September 10.

Located in Oak Bluffs, Massachusetts, United States. WALK TO BEACHES,HARBOR,EVERYTHING!! IN-TOWN OB! A/C,Large Deck,Gazebo,Yard ***IMPORTANT--PLEASE "MESSAGE " MANAGER ANNETTE FIRST----BEFORE SENDING A BOOKING REQUEST!! ( JUST CLICK ON " CONTACT HOST" (you will find 'CONTACT HOST" on the bottom of the listing on the mobile app and on the full website "CONTACT HOST' will be located just under where it says request to book ) THEN SEND MESSAGE ) ********IN-TOWN ! WALK TO EVERYTHING! **Great location!! Convenient IN-TOWN Oak Bluffs location - WALK TO EVERYTHING !!! : BEACHES, Flying Horses, Arcade, Movie Theater, ferry, harbor/marina, shops, art galleries, restaurants, outdoor bars,bike path, playgrounds, public library, ponds, walking trails, gingerbread cottages, parks, tennis, basketball courts , baseball field, golf, groceries.**Fabulous Gazebo screened tent with chairs and table! All sides unzip to screens only or use curtains for privacy! ** HI-SPEED WIRELESS INTERNET, AIR CONDITIONING in all rooms!! 55' 3D Smart TV in living room

Located in Oak Bluffs, Massachusetts, United States. Welcome to "Suzy's Place" Best Location! Walk Everywhere. Newly built in 2024. "Suzy's Place" is arguably the best location on the island. Your cozy getaway awaits in Oak Bluffs at this beautiful newly constructed house in 2024. Sleeps 5 with 1 king bed and 1 full sized futon in the bedroom. Plus, there's an additional living room space with a queen sofa pullout for extra comfort. This location is perfect for a tranquil retreat, with easy walking access to downtown. Nestled in the Heart of Oak Bluffs, directly behind the historic and charming Gingerbread Cottages. We are also directly across from "The Barn and Bistro" Restaurant for great food, entertainment and bowling. Enjoy the convenience of amenities like an iron, hair dryer, heating, WiFi, washing machine, and central AC. The bathroom features a new vanity with touch screen mirror, shower and heated tile floors. We also have a huge outside shower, a grille and small outside dining area. Make your holiday one for the books with a

Located in Oak Bluffs, Massachusetts, United States. Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs Island GetawayOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Find plenty of summer sunshine at this two-bedroom Oak Bluffs escape, a comfortable Martha's Vineyard getaway with a private deck, easy access to nearby beaches, and an ideal location within walking distance of downtown.This single-level home sits on a tranquil, dead-end street, just over a mile west of the Steamship Authority Oak Bluffs Terminal, the Flying Horses Carousel, and the lovely beaches in downtown Oak Bluffs. Take morning walks to lounge on the sand at Eastville Beach half a mile west, ride your bike each afternoon to Joseph Sylvia State Beach four miles south, and catch gorgeous sunsets at the East Chop Lighthouse one mile north.This spacious rambler boasts a bit of mid-century style, from the wood-paneled walls to the mod-inspired furnishings in the de

Located in Vineyard Haven, Massachusetts, United States. Secluded waterfront oasis w/private beach and mooring, dock, patio - 1 dog OK Lily HillOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Step back into a more peaceful time at this special home on the western shore of Lagoon Pond. Poised on a knoll overlooking the water, Lily Hill offers both serenity and sweeping views from impeccably maintained grounds. Enjoy a swim at your private beach morning, noon or night; rinse off in a hot water outdoor shower on the patio. Tie your sailboat or cruiser to the longest dock on the freshwater/saltwater lagoon, which opens to Vineyard Haven harbor; use the private, deep water mooring for your yacht. From the house, you watch the sunrise across the lagoon. From the end of the dock, with water lapping underneath, you can watch both the sunrise and sunset through the trees! Choose a unique spot to propose or hold an intimate wedding: Lily Hill's elegant gazebo overl

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

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

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

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

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

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