94,639 properties available

Located in Oak Bluffs, Massachusetts, United States. Historic Oak Bluffs home, short walk to town, beach, and harbor. Family owned and kept charming 19th century home in Oak Bluffs highlands near Baptist Temple park. This house is about 1/2 mile walk to ferry terminals for Island Queen, Vineyard Fast Ferry, Seastreak, Hy-Line and Steamship Authority (Oak Bluffs terminal). Three bedrooms total with two queen beds and one twin bed. Full bathroom upstairs with indoor shower, half bathroom downstairs, plus an outdoor shower. Window unit A/C's provided throughout (each bedroom has one A/C). For cooler months, the heating is a working wood stove and electric space heaters which are provided. 10-12 minute walk to downtown Oak Bluffs for all needs. Private parking for up to (4) vehicles. Charming wrap around covered porch in front, small deck in back with very private yard. Wifi internet to work remotely or stream shows/movies. Windows 10 PC available to display Netflix, Hulu, sports, etc. No cable TV.

Located in Oak Bluffs, Massachusetts, United States. Perfect one bedroom garage apartment with A/C This charming one bedroom is perfect for a couple or small family looking for a great space and in a great location just a mile from Downtown Oak Bluffs. Built in 2017, this unit has great amenities including A/C and stylish wood floors. The apartment is over the garage on a property at the end of a quiet street and offers COMPLETE privacy from the main house. There are two private entrances (one from inside the garage and the second one from stairs outside) along with two designated off-street parking spaces.The bedroom has a queen bed, plenty of storage and a wall-mounted Smart TV. There is a cozy kitchen with countertop seating and plenty of space to cook any meal. The living room has a brand new queen sleeper sofa and wall-mounted Smart TV.l. There is a washer/dryer in the garage for the sole use of apartment tenants.

Located in Oak Bluffs, Massachusetts, United States. Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town Mid-century rustic cottage charm tucked on 3 acres 1 mi to Oak Bluffs and Vineyard Haven center's. Acquired in 1950 by Lisa's grandparents, the original style of this family heirloom has been lovingly preserved. Comfortable new furniture with vintage accents, lovely linens, memory foam mattresses, lots of outdoor space and privacy, and convenient location defines this property. Walk to beach and bus stop. Direct bike path access. Open living and dining area, with separate kitchen. A covered outdoor breezeway connects bedrooms, shower room and bathroom to the main living area. There's a screen porch, outdoor porch, patio, and huge yard. Property is set back 100 yards from the road. Plenty of parking. Lots of great amenities! Memory foam and coil mattresses, nice pillows, soft cotton sheets and comforters, and soft blankets make sleeping very comfortable. Lovely thick cotton towels. Smart HDTV with Roku live TV, Netflix, HBO

Located in Oak Bluffs, Massachusetts, United States. Heart of Oak Bluffs, No Car Needed! Ocean Views, Walk to Everywhere! ** All August reservations are Saturday-to-Saturday. **Welcome to “Gem of the Ocean”! Martha’s Vineyard vacationers dream! This recently updated condo with private balcony and spectacular ocean views is within walking distance to everywhere in downtown Oak Bluffs and a front row seat to all the activity and attractions around Ocean Park: Inkwell Beach, Circuit Avenue, Linda Jeans, Flying Horses, Carousel, OB ferry and harbor, Campground Cottages, Tabernacle, Illumination, shops, restaurants and more! No car needed. Beautiful second floor 2 BR/1 BA condo sleeps up to 4 guests. The master bedroom has a king bed. The second bedroom has full and twin beds, The recently updated bathroom has a tub and shower combo, new vanity and chair height toilet. Amazing location with spectacular views! Located in an historical building, you’ll enjoy this bright and airy space, with views of the ocean and Ocean Park from the private

Located in Vineyard Haven, Massachusetts, United States. Contemporary Pet-friendly Retreat Contemporary with open living/dining area, cathedral ceilings, and air conditioning throughout. Sliding and French doors lead to wrap-around decks and a screened-in porch adjacent to the dining room. Outdoor shower.Walking distance from Lake Tashmoo and Vineyard Haven. A mile and a half to beautiful Tashmoo Town Beach. Lots of amenities including fully stocked kitchen, linens, gas grill, and digital piano. Located on very quiet, dead-end street surrounded by woods. Wireless, high speed Internet. Smart TV. Washer and dryer.Green features include solar panels for electricity generation, EV charging, and mini-splits for AC and efficient room-based heating.Beds: Queen in master bedroom, twin and trundle (sleeps 3) in second bedroom, full in third bedroom, futon sleep sofa in living room. Master bedroom has private bath with luxurious walk-in shower, .and sliding doors leading out to lower deck.Kitchen and bathrooms all updated.Pet-friendly.High sp

Located in Oak Bluffs, Massachusetts, United States. Charming home with deck, W/D, & amazing location Oak Bluffs DarlingOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located in the charming town of Oak Bluffs, MA, this house offers a cozy retreat for your Martha's Vineyard getaway. Just a short walk to the bike path on County Rd and moorings on the Lagoon Pond, this home is perfectly situated for outdoor enthusiasts. With wood floors and a quarter-acre leafy yard, this home provides a welcoming atmosphere. Relax in the hammock strung from a tree in the front yard or enjoy the spacious deck along the side and back of the house. A patio table and chairs for four with umbrella will be ready for your enjoyment. This dog-friendly property is equipped with all the amenities you need for a comfortable stay, including a high chair, Pack and Play, washer/dryer, internet, gas grill, and more. Whether you're cooking in the fully stocked kitchen or lounging in

Located in Oak Bluffs, Massachusetts, United States. Perfect location! Beach, Harbor & Town. Beautiful 1st Floor Apartment Oasis This lovely, in-town, first-floor apartment is in a renovated 1800's historic Oak Bluffs cottage with a fenced in landscaped patio. The beautiful stone patio out the kitchen door has plenty of seating, an outdoor shower, 2-person hot tub (please let us know if you think you will use it), propane bbq grill, and an outdoor designer Rais fireplace. The large and sunlit gourmet kitchen has skylights and is the heart of the home.This apartment accommodates up to 4 guests, with one very petite queen bedroom and a large living room that can be entirely closed off as a separate room, with a queen Crate and Barrel sofa bed. The room can be closed off from the rest of the apartment for privacy with glass french windows and doors and curtains, and can have a separate entrance as well. The very large country kitchen with every amenity you could hope for.There is one full bath (with tub/shower) in the apartment, and one add

Located in Oak Bluffs, Massachusetts, United States. The Nest, Comfortable, Cozy and Convenient The Nest is a private entranced guesthouse that is ideally located 2/3-1 mile walking distance to Oak Bluffs town, harbor, beaches and ferries (summer ferry service is in Oak Bluffs and Vineyard Haven, winter service is Vineyard Haven ONLY). We offer one bedroom with a queen bed and a queen sized sofa bed in the living space with a private bathroom. This newly remodeled space has a full service kitchen, air conditioning, heat, cable TV and WiFi all for your comfort and convenience. The Nest is waiting for nesters!

Located in Oak Bluffs, Massachusetts, United States. Spacious 1 Bedroom Apt - 3 min Walk to the Beach! A perfect place for 1-4 people to stay! You will have plenty of room, shared use of a grill, backyard, and outdoor dining area. Location is fantastic - it's only a 3 minute walk to the lagoon/beach, 20 minute walk to the Oak Bluffs harbor, 25 minute walk to downtown Oak Bluffs, and 7 minute drive to State Beach.We have central AC and heat to keep you comfortable no matter what the temperature is!The owners live upstairs with their two young kids (4 & 6). As such, this listing is for early-risers ready to enjoy the beauty of island mornings :)

Located in Vineyard Haven, Massachusetts, United States. Central 2nd-floor apartment with propane stove, grill, W/D, & great location Main Street UpperOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Tisbury Town Beach, Owen Park Beach, and Vineyard Haven shops, restaurants, and activities are all within a half-mile of this convenient Main Street retreat. Within walking distance of the ferry terminal and town services, this second-floor apartment also offers windows facing the harbor and Owen Park Beach. Leave the car behind while you explore around town or hop on the ferry to spend the day on Cape Cod. The sunny interior comes well-appointed for contemporary seaside living. The fully updated kitchen boasts a sparkling suite of all-new stainless steel appliances, including a dishwasher, for stress-free meal prep and planning. Plush seating, a propane stove, and a mini-split air-conditioner offer all-season comfort for group gatherings in the living room, w

Located in Vineyard Haven, Massachusetts, United States. Cozy Vineyard Haven Cottage < 1 Mi to Beach! Your next summer trip to Martha’s Vineyard starts at this vacation rental in Vineyard Haven! This 1-bedroom, 1-bathroom cottage is the ideal spot to discover all the top attractions the area has to offer. Bury your toes in the sand at Tisbury Town Beach, Oak Bluffs, or Lake Tashmoo, set out on a hike on the nearby wooded trails, and rent a bicycle to explore the island at your leisure. When the day is done, return home for a movie night before doing it all again tomorrow. The Vineyard awaits!-- THE PROPERTY --MassTaxConnect ID: C0224992960 | Near Ocean | Hiking Trail Access On-Site Bedroom: Full BedINDOOR LIVING: TV, dining table, ceiling fans, distressed wood, exposed beam ceilingsKITCHEN: Stove/oven, microwave, refrigerator, coffee maker, toaster, dishware/flatware, trash bags/paper towelsGENERAL: Free WiFi, washer/dryer, linens/towelsSUITABILITY: 2 steps required to access, single-story homeFAQ: No A/CPARKING: Driveway (1 vehicle)ADDT’L A

Located in Vineyard Haven, Massachusetts, United States. Charming Oak Bluffs Cottage: Prime Location, Stylish Comfort & Serene Privacy Charming Cottage in Oak Bluffs: Your Perfect Island Getaway!Welcome to our cozy and comfortable cottage in the heart of Oak Bluffs, where everything you need for a memorable vacation is just a short walk or bike ride away!Features:Spacious Wrap-Around Deck: Enjoy the expansive deck, complete with outdoor furniture and a refreshing outdoor shower—perfect for rinsing off after a day at the beach.Prime Location: Stroll or bike to nearby attractions like Sunset Lake, East Chop Lighthouse, Bistro Bowling Alley, The Arts District, Oak Bluffs Harbor, Circuit Avenue, Flying Horses Carousel, Inkwell Beach, Town Beach, the historic Campground Meeting Gingerbread Houses and Tabernacle, Union Chapel, great restaurants and the Oak Bluffs Steamship Authority terminal. The island’s bus service is conveniently located just outside the door, making exploring the rest of the island easy.The Cottage:Stylish & Homey: Our cottage

Located in Vineyard Haven, Massachusetts, United States. Well-Appointed 3 bedrm 4 bathrm with AC and 50+ 5-star reviews! *** IF INTERESTED IN BOOKING, PLEASE SEND AN INQUIRY (click on ’contact host’) PRIOR TO SENDING A BOOKING REQUEST. BOOKING REQUESTS SENT WITHOUT PRIOR CONFIRMATION OF AVAILABILITY CANNOT BE ACCEPTED.This spacious, beautiful, and well-decorated home is conveniently located at the end of a quiet residential street abutting 8 acres of conservation land. The house is fully furnished & equipped, exceptionally clean, and well-maintained. The main living area consists of a bright and airy open-concept space with cathedral ceiling, multiple skylights, central AC plus a ceiling fan. There is also radiant heat throughout the house and a fireplace in the living room. The state-of-the-art, fully appointed kitchen has a large island, granite countertops and Jenn-Air stainless appliances. Home is tastefully decorated throughout with a mix of antique and modern furnishings as well as oriental rugs and original artwork. The master bedro

Located in Vineyard Haven, Massachusetts, United States. Steps to the beach - Vineyard Summer home This charming summer cottage offers the quintessential vacation experience close to Vineyard Haven center. Walk to the beach at the end of the lane in this quiet residential neighborhood in West Chop. The art collector owner provides a delightful setting for your family vacation. Large family room with gas-fired fireplace is perfect for evening gatherings. Expansive yard allows ample room for outdoor games and activities. Two bedrooms, one bath, plus sleep sofas accommodates 5-6. SATURDAY TO SATURDAY RENTAL

Located in Oak Bluffs, Massachusetts, United States. Big Beach House - Ocean Views! Original 1900 Victorian home, updated in 2006, located in the historic Copeland District just one block from the beach. Three story home boasts decks and wrap around porch with ocean views from each. Five large bedrooms, spacious living room with French doors that open to the large wrap-around porch. Enjoy relaxing meals in the formal dining room and eat-in kitchen. Rec room in basement includes stone dry bar and 55' wide screen TV. Original wood paneling throughout. Fenced in back yard for privacy, perfect for post-beach barbecues. On Waban Park. 5 minute walk to town and Back Door Donuts; 1 minute hop, skip or jump to Oak Bluffs town beach/Inkwell.

Located in Oak Bluffs, Massachusetts, United States. Coastal home with outdoor shower, grill, fireplace, central AC, & W/D Yellow Brick Road HouseOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Bright and inviting, this home provides an ideal escape for your family's next coastal vacation. Venture to nearby beaches and eclectic shops during the daytime, then return home to spend more time outdoors in your spacious backyard. Rinse off in the outdoor shower before you fire up the propane grill for a barbecue. Listen to favorite playlists on the speakers while you dine at the shaded six-person dining table. A hammock provides a convenient spot to kick back with a good book, while the front yard offers more space for lawn games.Large windows invite natural light into the living area. Cozy up by the gas fireplace while you stream favorite shows on the smart TV. Outfitted with stainless steel appliances, the modern kitchen features everything you need to wh

Located in Oak Bluffs, Massachusetts, United States. Comfortable Island Home, Easy Access to Beaches and Town Salt Box style Log Home with open floor plan built by my family with a country feel, located on a wooded lot in the down island town of Oak Bluffs. Central Air and easy walk to local beach that is used by families of the Lagoon Heights area. Beautiful town and state beaches close by. Charter fishing, golf, great restaurants and ample shopping for the occasional rainy day. Many local attractions to visit, gingerbread homes, tabernacle, oldest functioning carrousel, walking/ bike trails and nature preserves to keep one busy while enjoying the the Vineyard's laid back, casual nature. First floor bedroom has queen bed, upstairs has the full bed. Loft area has three twin beds. Screened porch has wicker furniture, two couches and two comfortable chairs. The home provides a comfortable retreat for those that prefer to be away from crowds, yet only a short trip to town and the beaches.*If not able to bring your own linens, they

Located in Oak Bluffs, Massachusetts, United States. Fully Renovated & Spacious home walking distance to downtown Oak Bluffs/Beaches Newly renovated three-level home with 3 bedrooms 2 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 6 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 2 twin beds. Master bedroom with b

Located in Vineyard Haven, Massachusetts, United States. Your Summer Home - Close to Beach, Shops, Cafes, & Ferry! 50+ ⭐️⭐️⭐️⭐️⭐️ Reviews With more than Fifty, 5-STAR REVIEWS, you can book with confidence. This beautifully appointed home features luxe furnishings throughout the house. Three generous bedrooms including a first floor master bedroom, 2 and a half bathrooms, large livingroom with bright sunroom, kitchen, with dining area, and beautiful large deck for relaxing and dining. AC, Wifi, Satellite TV all included. A short 5-10 minute stroll to local beaches, and a15-20 minute walk to all of the shopping of charming downtown Vineyard Haven.

Located in Vineyard Haven, Massachusetts, United States. Walk-up apartment with deck & grill - walk to beach & town Everyday is SaturdayOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Find yourself within easy reach of the best Martha's Vineyard offers with this cozy walk-up apartment. Just a short walk from the Steamship Authority Terminal and downtown Vineyard Haven, the home is also close to local town beaches. Golfers in the group will appreciate a convenient location close to Mink Meadows Golf Club. Walking trails from the home offer a three-mile loop to and from the scenic West Chop, offering some of the finest sunset views on the island. Beach chairs and various board games and playing cards are also provided for family fun and convenience. At home, you can enjoy outdoor living on the private deck and fire up the gas grill for summertime barbecues in the backyard.The sunny interior comes well-appointed for home comfort. The tidy kitchen area has a

Located in Oak Bluffs, Massachusetts, United States. Spacious 4 BR Home, Steps to Lagoon, Minutes to Downtown Oak Bluffs and Beaches! Spacious two-level four-bedroom house within steps to lagoon located in Oak Bluffs and within minutes to Downtown and beaches! Features both a separate living room and family room, two full bathrooms, a fully-equipped kitchen, and as a bonus has a screened-in porch to enjoy your morning coffee! This lovely home also has a large front and back yard, as well as a separate driveway. As another bonus, it comes with two cars for additional rental! Great for families. Sorry, no pets allowed. We have had many satisfied, repeat visitors!

Located in Oak Bluffs, Massachusetts, United States. Quaint,,,Quiet..up island feel yet a short walk to to , x ,, z wn and harbor Your quintessential summer vacation starts here! The property has a combination of a strong rental history(read rental reviews) and a lot of repeat guests. the house and guesthouse will make this rental a true summer getaway - all the feature comforts both inside and out! Comfortable beds and, luxury bath towels, furnishings, built-ins, central air, lighting, rugs, art work, and more! The spacious yard will encourage plenty of lounging under the shade trees, as well as an large area designated for outdoor games. The exterior deck is large enough to host the gas grill, dining table (with umbrella), seating for 6-8, as well as a private outdoor shower. All you need to clean up after a day at the beach, enjoy a few cocktails and get your BBQ going. A short walk to town and harbor and just around the corner from the campground cottages, yet set on a very quiet street with an up-island feel !! Wifi an

Located in Oak Bluffs, Massachusetts, United States. Discover the magic of Martha’s Vineyard! NEW ! Build in 2020 ! Build in 2020 ! New lovely studio apartment.Clean, bright and comfortable.700 sq feet !Great for couples, work trips, weddings.The spaceOur new studio is located above the garage attached on the side of the main house.Private entrance.There is a small outdoor deck on top of the stairs to the studio.The interior offers high ceilings, A/C, TV, wifi, cute kitchen, and lots of light. There is a queen sized bed and sofa.•Bike to town, the harbor, restaurants, shopping, Flying Horses carousel, and the arcade•Easy drive to State Beach•10 minutes from the ferryNEIGHBORHOOD Oak Bluffs is our favorite town for families visiting the Island - offering some of the best restaurants, ice cream parlors, fun shopping, the historical gingerbread cottages and the famous Flying Horses carousel! The harbor is a great place for a stroll to look at the amazing collection of boats from the Pirate ship to private yachts, and don't miss beautiful O

Located in Oak Bluffs, Massachusetts, United States. Private Waterfront, Beachfront, and 90' Dock. Views. Newly Renovated 3Bd 2.5Bath Spectacular water views from classic Martha's Vineyard waterfront home! Perched atop a bluff overlooking the Nantucket Sound and the wide lagoon between Oak Bluffs and Vineyard Haven.Secluded and private, yet only a short distance from the two main Martha's Vineyard downtowns. Use the house as home base and a central location to explore all of the sights, shopping and seafood that Martha's Vineyard has to offer, or stay home and 'get away from it all'. Spend your time relaxing in the sun on the brick patio or the shade on the outdoor lanai while you take in the views and feel the cool breeze from over the water. Enjoy the flowering beautiful landscaped yard, or take a walk and relax on the private beach or dock.Perfect for a romantic getaway for two, or for a special family vacation.