27,207 properties available

Located in Oak Bluffs, Massachusetts, United States. Oak Bluffs Retreat - The perfect getaway! Six minute drive to beach! This two floor beauty with central AC boasts ample yard space and all the amenities you look for in a vacation home.The two bedrooms on the top floor feature private baths to assure the right amount of privacy. One bedroom offers a queen bed, while the other has twins. The den on the top floor is furnished with a daybed that can also sleep two twin size or be converted to one king size bed.The fully equipped kitchen comes complete with stainless steel appliances and faces a wrap-around dining area, which can easily accommodate six.The deck, located right off the kitchen, features seating for your favorite hot beverage in the morning and a tall bar table for your afternoon and evening cocktails. Those with an appetite for grilling can take advantage of the Weber gas grill and dine outdoors on the two nearby picnic benches.As you step down off the deck, to your left is an outdoor shower. Continue walking toward the shed

Located in Vineyard Haven, Massachusetts, United States. Greek Revival-Inspired In-Town Luxury Getaway POINT B EXCLUSIVE - This new home is a modern take on a Classic Greek Revival and it has it all -- three living levels of luxurious living with stylish touches and amenities throughout, plus a great in-town location.The first floor features an open Great Room with Living, Dining, and Kitchen Areas. The Living Area anchors one end of the space. It has sofa and chair seating with large screen TV. The Dining Area sits between the Living Area and Kitchen. The sunny Cook's Kitchen anchors the other end of the Great Room. The large Kitchen features center prep island/breakfast bar, stainless and cabinet-fronted commercial appliances, quartz counters, plus a sunny breakfast nook with three walls of glass windows and seating for six. The Primary Bedroom is also on the first floor with a deluxe en suite bath. The other three Bedrooms are on the second floor and all feature private en suite baths as well. The lower walk-out level has a large Media/Ga

Located in Oak Bluffs, Massachusetts, United States. The Island Collection MV: Enjoy This 1850s Victorian Home With Ocean Views! Enjoy a relaxing ferry ride to Oak Bluffs and its picturesque surroundings. Once your ferry ride ends, you’re steps away from home! This newly renovated, elegant, enchanting, and historical bright yellow Victorian home was built in the 1850s. Speaking of ocean views….enjoy the benefits of having an ocean view right in your front yard! Located on Ocean Avenue you can see the entire ocean from this lovely home, which has 7 bedrooms, 4 full bathrooms and comfortably sleeps 14 people. There is one parking space available on the street, a gas grill on the back patio, and an outdoor shower for your convenience.As you enter the home, you will be amazed at the beauty of the fireplace. On the first floor, enjoy an ocean view room with a fireplace. There is also one large bedroom with one queen bed and one twin bed. On the second floor, enjoy a beautiful and cozy ocean view room with a telescope. There are also five bed

Located in Vineyard Haven, Massachusetts, United States. Luxurious Contemporary Near The Lagoon POINT B EXCLUSIVE - This recently built luxurious Contemporary is quietly tucked away by The Lagoon and Martha's Vineyard Museum in Vineyard Haven.The home features a modern first-floor layout with open Living, Dining, and Kitchen Areas. The Living Area is framed by a wall of windows on one side, and centered around a large screen TV with sofa and chair seating. There is a center stairway that divides the first-floor open space with the Living Area on one side and the Dining and Kitchen Areas on the other side, with walk-around access on both sides of the staircase.The Dining Area is framed by two walls of glass windows and opens to the Gourmet Kitchen for easy entertaining. The Cook's Kitchen is nicely-equipped with commercial stainless appliances, center prep island/breakfast bar, and quartz counters. A sliding door off the Kitchen opens to the back deck for outdoor dining and entertaining.One of the Bedrooms, plus an Office with pull-out sofa s

Located in Oak Bluffs, Massachusetts, United States. The Island Collection MV: Charming Cottage Located In Heart Of Oak Bluffs Enjoy a relaxing ferry ride to Oak Bluffs and its picturesque surroundings. Once your ferry ride ends, you’re steps away from home! Your vacation stay will be unforgettable in this charming cottage located in back of the elegant, enchanting, and historical bright yellow Victorian home, which was built in the 1950s. Speaking of ocean views….enjoy the benefits of having an ocean view steps away from your back yard! Being on vacation in Martha’s Vineyard in the heart of down town on a main street has its privileges! As the cottage is located on the main street, Kennebec Avenue, you can see the entire ocean; only a stone’s throw away from this lovely fully furnished cottage, which has 2 full bedrooms, 2 full private bathrooms (upstairs), and 1 powder room (located on the main level). The cottage comfortably sleeps four people; two couples or a family of four. There is one parking space available to you next to the

Located in Oak Bluffs, Massachusetts, United States. Large home with great yard, firepit, Peloton & home office - walk into town Glenn ManorOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Spend a summer to remember at this spacious and comfortable Martha's Vineyard home, ideally located within walking distance of the lagoon and downtown Oak Bluffs. Enjoy a classic, covered front porch, a large yard with a play structure for the kids, and a beautiful back deck and patio where you can gather around the firepit in the evenings.This two-story home enjoys a particularly convenient location in Oak Bluffs, less than a quarter-mile up the road from Eastville Beach and the lagoon. It's less than a mile stroll to the shops and restaurants of Circuit Avenue, and barely over a mile to the Flying Horses Carousel, Inkwell Beach, and the Oak Bluffs Ferry Terminal. The only hospital on the island is within half a mile, and downtown Vineyard Haven (two miles) is easil

Located in Oak Bluffs, Massachusetts, United States. The Island Collection MV: Experience a Luxury Getaway by the Lagoon This beautiful 3 bedroom home is located in a quiet area on Martha’s Vineyard by Lagoon Pond. When you walk inside, you will be delighted by the beach stone fireplace and the comforting ambience. It presents gorgeous “costa esmeralda” granite counter tops with solid cherry cabinets, stainless steel appliances, and a kitchen which integrates to the dining area that sits 8 people. From there, the french doors invite you to a relaxing patio surrounded by artisan landscaping. The patio, complete with cobblestones, also has a grill and it is a fun place for a family BBQ. An outdoor shower is a great way to rinse off after a swim in the Lagoon. The master bedroom is located on the first floor and features a walk-in closet and a bathroom with calcutta gold marble, his and her sinks, a rain shower, and a cast iron herring bone tub. The den has a comfy couch and a flat screen TV mounted on the wall, which is perfect for movie

Located in Oak Bluffs, Massachusetts, United States. Family-built Oak Bluffs property in a great location with kitchens & hot tub Frazier CircleOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Lovingly built and owned by the same family since 1971, Frazier Circle offers plenty of space for your next family or friend getaway! The property is nestled minutes away from the Oak Bluffs ferry terminal, Town Beach, Inkwell Beach, and numerous shops and restaurants. Fun in the sun continues right at Frazier Circle as the property boasts ample outdoor living space and a screened-in gazebo equipped with a hot tub. Inside, you'll have no issues getting cozy amidst the vaulted ceilings and warm wood finishes in the open living rooms. With gas fireplaces, oversized sofas, and smart TVs, these spaces are perfect for peaceful evenings in. Breezy cooking sessions are inevitable in well-equipped kitchens, framed by gleaming tile backsplashes. With five bedrooms to spra

Located in Vineyard Haven, Massachusetts, United States. Classic home with screened porch - walk to town, beaches & Lake Tashmoo The Fish BowlOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Wonderfully peaceful yet only a short walk from Lake Tashmoo, island beaches, and the heart of the village, this cottage is a Vineyard Haven classic. Here among the trees, you'll have a delightful screened porch for your morning coffee, a deck for sun-splashed afternoons, and easy access to the best of Martha's Vineyard.This single-story home sits less than a mile from the center of Vineyard Haven, a position that allows for easy walks to the ferry terminal, great restaurants, independent shops, and summer theater. When it's time to get out in the sunshine, charter a boat to take out on the lake (less than a mile) or lounge on the shores of Tisbury Town Beach, Owen Park Beach, or Lake Tashmoo Town Beach (all within a mile and a half). Whether you spend your summer days

Located in Oak Bluffs, Massachusetts, United States. Beautiful and Modern 4Bdrm, 3Ba Colonial w/ a large yard in Historic Oak Bluffs! This two-story, well-appointed Colonial boasts plenty of parking and an expansive backyard in a quaint neighborhood at the center of a cul-de-sac. It is located within a 20-minute walk and 5-minute drive from Circuit Avenue, Inkwell Beach, the harbor, ferry, shops, restaurants, ice cream parlors and much more. You and your family will instantly feel welcomed in this beautiful home featuring 4-bedrooms and 3-full baths - including one that is ensuite! The airy first-floor features an open concept living room, kitchen & breakfast bar for 4, a queen bedroom, and 1 full bath with plenty of natural light. Off of the dining area is a glass double-door entrance allowing easy access to the deck, which features tables, chairs and a built-in bench that seat 8-plus, a patio, a grill, and a well-maintained backyard to enjoy a barbeque with family and friends. The second floor leads to two pleasant bedrooms and a Med

Located in Oak Bluffs, Massachusetts, United States. Spacious home in central location with beautiful patio, pool table, W/D, & AC Bird Street BreezeOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Nestled in a quiet neighborhood next door to the public library (with access to EV chargers), this bright and airy house in Oak Bluffs, MA, offers the perfect retreat for your vacation. Conveniently located within walking distance to shops, restaurants, galleries, the harbor, and beaches, this house is a hidden gem. With four spacious bedrooms, including two with private decks, you can enjoy your morning coffee or evening nightcap while taking in the serene surroundings. Enjoy the private pool table in the lower level game room complete with comfortable seating and beautiful TV.The open concept kitchen, dining, and living room area is ideal for entertaining, with seating for eight. The kitchen boasts stainless steel appliances, quartz countertops, and a lar

Located in Vineyard Haven, Massachusetts, United States. In Town Historic Captain's house An elegant historic Captain’s house 2 blocks to downtown, the ferry, town pier and beach, and restaurants. An expansive garden (double lot), patio, and outdoor dining make this property a refuge in the heart of Vineyard Haven. This historic house was built in 1905 by Captain George Eldridge who in 1875 first published the famous tide schedules still used by sailors today. On Main St, a short walk from the downtown, “Fairtide” sits on a double lot with expansive lawn and gardens. The kitchen was recently remodeled and the house is well kept and cared for. Original douglas fir floors, a piano, 65" TV, indoor and outdoor dining, outdoor shed and garage, zipline, bikes. Linens and everything needed for the beach (umbrellas, chairs, toys) are provided.

Located in Oak Bluffs, Massachusetts, United States. Remodeled and historic, beautiful Oak Bluffs home. Walk to Town and Ferry. This is a beautifully remodeled, and meticulously maintained house in Cottage City. The property is a short walk to town, walk to beach, and walk to ferry. Walk to town to see the Gingerbread houses, Flying Horses, the Harbor, and the many bars and restaurants, or walk to the stretch of Town beach.

Located in Vineyard Haven, Massachusetts, United States. In-town Jewel -- Vineyard Haven Classic Cape Cod home, 5 short blocks from the heart of downtown Vineyard Haven and the Island ferry terminal. The house has been thoughtfully-renovated, resulting in guests who come again and again.Located in a quiet neighborhood, this traditional home sleeps 7 guests in 4 bedrooms with 2 baths. Guests can leave the car in the driveway and leisurely stroll into town for a morning cup of coffee, breakfast, lunch, dinner, shopping or to catch a bus at the ferry terminal to visit other parts of the Island. The first floor offers a spacious living room with fireplace, game table and cable TV. The dining room opens into a kitchen gleaming with granite counter tops, stainless steel appliances and a breakfast bar. For outdoor eating, the kitchen conveniently opens onto a private and nicely landscaped, bluestone patio with table/chairs/umbrella and BBQ grill. Around the corner is an enclosed outdoor shower for a quick rinse after a sandy day at the beach. Slee

Located in Oak Bluffs, Massachusetts, United States. Modern Martha's Vineyard Retreat in Oak Bluffs New construction home in Oak Bluffs. Enjoy a modern, clean and peaceful stay in the Vineyard. This home is mins to downtown Oak Bluffs, close to the Sail Camp and MV Beaches. Enjoy being close to everything, while also having a relaxing retreat.

Located in Oak Bluffs, Massachusetts, United States. Dog-Friendly Downtown Home w/Free WiFi, Deck, Water Views, & Partial A/C Marsh WalkOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Outdoor relaxation at its best awaits at this dog-friendly home! This ground-floor retreat offers great outdoor space with a completely furnished deck with a great seating area and an outdoor dining area. Now you can unwind with your family or friends (and the dog), take in the scenery, and simply relax. Inside, the living room is another great place to relax with two sofas and a flatscreen TV with streaming services. There are plenty of board games as well, perfect for trivia night! The kitchen is separate from the living room but close enough to the dining area, which has a dining table that seats four. The kitchen has your back with great appliances and cookware to whip up the most delicious meals during your stay. There are three bedrooms and one full bathroom.Things

Located in Oak Bluffs, Massachusetts, United States. Charming Gingerbread Cottage in Historic Campgrounds in Oak Bluffs Sleeps Nine Extra-large gingerbread cottage in historic Campgrounds in Oak Bluffs, sleeps nine. Located on a double lot in the heart of the Martha's Vineyard Camp Meeting Association in Oak Bluffs, this extra-large cottage has five bedrooms and sleeps nine comfortably. The cottage has two full baths, both of which were completely renovated over the past few years. One with a cast iron tub and one with a tiled shower. A completely private outdoor shower made from cedar and accessible by a raised walkway from the back door of the house is the perfect place to clean off after the beach or simply to enjoy the fresh air with the morning shower. Set back from a wide quiet street, the house is a five minute walk from Oak Bluffs downtown and harbor. The covered wraparound front porch is the perfect place to enjoy the morning coffee or dinner on a summer evening. The porch boasts a classic porch swing, wicker rocking chai

Located in Vineyard Haven, Massachusetts, United States. New Suite with WiFi, Grill & Deck - Walk to Town, the Ferry & Beaches The Mermaid SuiteOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Enjoy the sparkling new construction of this studio-style Vineyard Haven property, a bright and sunny in-law secondary suite. It offers travelers a shared outdoor deck (with your own designated space), a gas grill for summer barbecues, and an ideal location within walking distance of town, the beach, and the ferry.This single-level studio sits in a quiet residential neighborhood, less than a mile from the Vineyard Haven Steamship Authority and the heart of downtown. Spend your days swimming at Owen Park and Tisbury Town Beaches one mile east, watch the sunset at the West Chop Lighthouse two miles north, and catch lively performances at the Martha's Vineyard Playhouse a half-mile walk from home.Built in 2017, the Mermaid Suite is a private suite located within a large

Located in Oak Bluffs, Massachusetts, United States. Charming MV Cottage: Walk to Dtwn Oak Bluffs! There's no better way to experience the laidback lifestyle of the Vineyard than in the heart of it all at this traditional 3-bedroom, 2-bath Oak Bluffs vacation rental. Tucked away just a short walk from Circuit Avenue, this cottage is ideal for travelers seeking easy access to the coast and an abundance of family-friendly attractions. The family-run shops, quaint harbor villages, 'gingerbread houses,' and shockingly beautiful beaches will have you falling in love with the island in no time!-- THE PROPERTY --MassTaxConnectID C0215152210 | Half Mile to Circuit Ave | 1 Mile to Inkwell Beach | Beach Gear ProvidedWarm, welcoming, and filled with old-school New England charm, this Martha’s Vineyard cottage hosts the perfect setting for any occasion, whether it be a family vacation, summertime wedding, or spontaneous weekend getaway.Bedroom 1: King Bed | Bedroom 2: Full Bed | Bedroom 3: Full Bed | Screened Porch: Daybed | Living Room: Queen Sleep

Located in Vineyard Haven, Massachusetts, United States. Walk to town/ferry, beach amenities, flat-screen TV, WiFi This bright, cheerful home is the perfect vacation spot for your family and friends. This Sunday to Sunday rental sleeps nine comfortably and is only an eight minute walk from shopping and fine dining in Vineyard Haven! The house is conveniently located on a bus route.If you prefer to eat at home, the home has a kitchen designed to please the avid chef and even boasts a wine refrigerator so you can enjoy your favorite vintage during your stay. The spacious yard and patio are perfect for relaxing or grilling with friends and family. Amenities for summer fun include beach chairs,beach towels and umbrella, cable, flat-screen TVs and DVD player, wireless internet, board games, and beach reads. Within walking distance of the Vineyard Haven ferry and just 3 miles from Oak Bluffs so just drop on by! The House sleeps seven (7) people during the months of May & June The House sleeps nine (9) people during the months of July & August

Located in Oak Bluffs, Massachusetts, United States. Inca Gardens Apt. New To Market - Lg Patio - Pets Inca Gardens is a 2nd-floor apartment of a cute house located in a quiet area of Martha's Vineyard between Oak Bluffs and Vineyard Haven. This vacation rental is the entire 2nd floor of this home. You will have the exclusive use of two large wrap-around decks and a large backyard patio with a fire pit, lounge area, and dining area. The owner is a master gardener and esthetician. This shows in her wonderful flowers, yard and attention to detail. The owner lives in the first floor of this home. There are two private and separate entrances to the home to insure your peaceful vacation. The home was recently remodeled and the entire inside was repainted. The owners have really gone all out to make a good impression to their guests along with our advice on how to make an appealing and welcoming home. There is a private side area with parking for two cars. High-Speed Internet (1 Gigabyte Plan) and a large eat-in kitchen and dining area complet

Located in Oak Bluffs, Massachusetts, United States. Beach and downtown OB walkable! 5 Bedroom Victorian on the park. You will find this 5 Bedroom Victorian quite charming with its bright & cheery interior. Located right across from wide open Waban park you can enjoy flying a kite or perhaps throwing a frisbee. Then grab your beach towel for a swim in the ocean just a block up the road. This desirable location is close to everything, including the ferry, circuit ave shops & restaurants, the tabernacle, bike path & bus route. Enjoy the 2nd floor balcony from your bedroom that offers a peek of the ocean.

Located in Oak Bluffs, Massachusetts, United States. Cute 4-BR House within walking distance of Circuit Avenue It is all about location! Leave the car at the house, and walk right into town. This 4 bedroom, 2 bath home features a large porch with a sitting area, air conditioner, a mahogany deck, and an outdoor shower.The first floor features a spacious eat-in kitchen, dining, and living room areas. You will find a large queen bedroom on the first floor. The second floor has the master bedroom with a queen bed and two smaller bedrooms each containing (1) twin bed.Located on a quiet street behind Sunset Lake, enjoy a 5-minute walk to nearby Circuit Avenue, the ferry, harbor, beach, and the library.

Located in Oak Bluffs, Massachusetts, United States. Walk to Beach and Town. Large Family House. -Seven air conditioned bedrooms-Four bathrooms-One living room and two small sitting rooms -large bluestone patio with outdoor kitchen, dining and outdoor living space-wraparound porch-walk to beach, two block/five minute walk-walk to town-beach chairs, coolers and beach towels provided-linens provided-outdoor showerKeywords: Oak Bluffs rental, martha's vineyard vacation rental, martha's vineyard house, oak bluffs lodging,