Oak Bluffs
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Oak Bluffs - or 'OB' - is a classic beach town, filled with tons of fun! Enjoy the sandy beaches along the calm waters of Nantucket Sound, events held in Ocean Park and the Tabernacle, and the casual atmosphere of the harbor and Circuit Avenue. Popular attractions include the Flying Horses Carousel, the nation’s oldest operating platform carousel, and the Martha’s Vineyard Camp Meeting Association, a National Historic Landmark and community of over 300 charming Victorian gingerbread cottages surrounding a beautiful iron Tabernacle. Circuit Avenue is always bustling and has something for everyone – ice cream, coffee shops, eateries, bars and boutiques. The Harbor is entirely walkable and is a great place to relax and watch the boats coming and going. Outside of the downtown area, there are many areas in OB that offer a quieter atmosphere. Contact us and we'll help you find the perfect getaway!
126 properties available
Welcome to your dream vacation home in Oak Bluffs, Martha's Vineyard! This exquisite property offers a luxurious and unforgettable experience in a prime location.
With four spacious bedrooms and three well-appointed bathrooms, this three-level house provides ample space for relaxation and privacy. As you step inside, you'll be greeted by a bright a
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Oak Bluffs 844
Welcome to your dream vacation home in Oak Bluffs, Martha's Vineyard! This exquisite property offers a luxurious and unforgettable experience in a pri... Read More
Welcome to your dream vacation home in Oak Bluffs, Martha's Vineyard! This exquisite property offers a luxurious and unforgettable experience in a pri... Read More
A classic Vineyard home close to Lagoon pond! This stylish and modern home includes space to roam throughout. This home includes an open floor plan with a well appointed kitchen, lovely dining area and a spacious living room. The first floor bedroom is en suite and offers a private deck. The remaining bedrooms are on the second floor with a sitting
Oak Bluffs 893
A classic Vineyard home close to Lagoon pond! This stylish and modern home includes space to roam throughout. This home includes an open floor plan wi... Read More
A classic Vineyard home close to Lagoon pond! This stylish and modern home includes space to roam throughout. This home includes an open floor plan wi... Read More
The J. A. Norton House has all the vintage charm of the 1870s but offers every summer vacationer's dream for convenience and enjoyment. Located three houses from the Inkwell, this three-bedroom, two-bath house is your summer destination. Its three-sided porchand fenced yard are perfect for relaxation with great views of the ocean and quick access t
Oak Bluffs 829
The J. A. Norton House has all the vintage charm of the 1870s but offers every summer vacationer's dream for convenience and enjoyment. Located three ... Read More
The J. A. Norton House has all the vintage charm of the 1870s but offers every summer vacationer's dream for convenience and enjoyment. Located three ... Read More
Indulge in the ultimate vacation experience at this well-appointed cape-style home, designed to provide peace and comfort to its guests. Step outside and bask in the enchanting outdoor sitting area with high-quality furniture, surrounded by a fenced-in yard and welcoming farmer's porch, perfect for savoring your morning cup of coffee.
Inside, you'l
Oak Bluffs 8119
Indulge in the ultimate vacation experience at this well-appointed cape-style home, designed to provide peace and comfort to its guests. Step outside ... Read More
Indulge in the ultimate vacation experience at this well-appointed cape-style home, designed to provide peace and comfort to its guests. Step outside ... Read More
Enjoy a relaxing afternoon on the spacious front porch of this charming Victorian home, located just moments from downtown Oak Bluffs. Stroll to the historic Flying Horses Carousel, browse unique shops, or spend the day at nearby beaches—all within easy reach.
Inside, the home offers four comfortably appointed second-floor bedrooms, a fully equippe
Oak Bluffs 8160
Enjoy a relaxing afternoon on the spacious front porch of this charming Victorian home, located just moments from downtown Oak Bluffs. Stroll to the h... Read More
Enjoy a relaxing afternoon on the spacious front porch of this charming Victorian home, located just moments from downtown Oak Bluffs. Stroll to the h... Read More
Just under a mile from downtown Oak Bluffs, this inviting 4-bedroom Cape combines comfort with a great location. Spend your days at Inkwell, Pay, or State Beaches, or head into town for ice cream, shopping, and dining—all just minutes away.
Back at the house, relax on the sunny deck, enjoy a quiet moment in the porch rocking chairs, or take advanta
Oak Bluffs 8814
Just under a mile from downtown Oak Bluffs, this inviting 4-bedroom Cape combines comfort with a great location. Spend your days at Inkwell, Pay, or S... Read More
Just under a mile from downtown Oak Bluffs, this inviting 4-bedroom Cape combines comfort with a great location. Spend your days at Inkwell, Pay, or S... Read More
Newly furnished, four-bedroom property in the Meadow View Farms. Enter into a large foyer with a sitting room to the left and a dining area on the right. A den is set off to the side of the dining area. The large well-equipped kitchen looks out to the vaulted ceiling main living area with two French doors leading to the outside deck (new gas grill
Oak Bluffs 8092
Newly furnished, four-bedroom property in the Meadow View Farms. Enter into a large foyer with a sitting room to the left and a dining area on the rig... Read More
Newly furnished, four-bedroom property in the Meadow View Farms. Enter into a large foyer with a sitting room to the left and a dining area on the rig... Read More
Bellavista at the Seaview. Step inside this second-floor contemporary condo, completely renovated with a natural colors and lots of textures. The kitchen, living space, and primary en suite bedroom are all about the view. The second bedroom and hall bath create a semi-private suite for guests. Sit on the deck and watch the sunrise over Inkwell bea
Oak Bluffs 842
Bellavista at the Seaview. Step inside this second-floor contemporary condo, completely renovated with a natural colors and lots of textures. The kitc... Read More
Bellavista at the Seaview. Step inside this second-floor contemporary condo, completely renovated with a natural colors and lots of textures. The kitc... Read More
Located at the end of a quiet, dead-end road just one mile from Oak Bluffs center, this renovated four-bedroom, three-bath home offers comfort, convenience, and plenty of charm. Enjoy new furnishings, updated appliances, and modernized bathrooms throughout. The open living and dining area features a cathedral ceiling that enhances the spacious feel
Oak Bluffs 8020
Located at the end of a quiet, dead-end road just one mile from Oak Bluffs center, this renovated four-bedroom, three-bath home offers comfort, conven... Read More
Located at the end of a quiet, dead-end road just one mile from Oak Bluffs center, this renovated four-bedroom, three-bath home offers comfort, conven... Read More
Sparkling Vineyard reverse level cottage has the fresh airy updates with painted white shiplap for wall decor, hardwoods and stainless steel to complete this modern beach house. From the open floor plan of dining, living and kitchen with walk out to the deck enjoy entertaining and keeping everyone together all on the second floor as well as a half
Oak Bluffs 8011
Sparkling Vineyard reverse level cottage has the fresh airy updates with painted white shiplap for wall decor, hardwoods and stainless steel to comple... Read More
Sparkling Vineyard reverse level cottage has the fresh airy updates with painted white shiplap for wall decor, hardwoods and stainless steel to comple... Read More
This lovely pond front property is situated in the private and peaceful association called Sengekontacket. This association offers tennis, a boat launch, dock and small club house and is overall a great neighborhood. On the first floor is the primary suite with a shower and separate tub. All remaining bedrooms are on the second floor and are connec
Oak Bluffs 8067
This lovely pond front property is situated in the private and peaceful association called Sengekontacket. This association offers tennis, a boat laun... Read More
This lovely pond front property is situated in the private and peaceful association called Sengekontacket. This association offers tennis, a boat laun... Read More
Envision your vacation at this Four-bedroom contemporary home in a luxury private community of The Preserve in Oak Bluffs. There's two primary en-suite bedrooms, one located on the first floor and the other on the second floor. Both of these en-suite spa-like bathrooms offer deep soaking tubs, a separate large shower stall, double sinks, and marble
Oak Bluffs 8176
Envision your vacation at this Four-bedroom contemporary home in a luxury private community of The Preserve in Oak Bluffs. There's two primary en-suit... Read More
Envision your vacation at this Four-bedroom contemporary home in a luxury private community of The Preserve in Oak Bluffs. There's two primary en-suit... Read More
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