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!
121 properties available
The charming five-bedroom gingerbread beach cottage is strategically located on Ocean Park in the center of Oak Bluffs. Bird's eye view of all that is happening in the village at your fingertips. This home is in a prime location for the annual fireworks and Illumination Night, which are held every August. It features two front decks, providing an i
Oak Bluffs 8124
The charming five-bedroom gingerbread beach cottage is strategically located on Ocean Park in the center of Oak Bluffs. Bird's eye view of all that is... Read More
The charming five-bedroom gingerbread beach cottage is strategically located on Ocean Park in the center of Oak Bluffs. Bird's eye view of all that is... 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
Contemporary Cape in Oak Bluffs- Nestled between the Lagoon Sailing Camp Park and Farm Neck Golf Club, this contemporary Cape offers comfort, space, and classic Vineyard charm. Step onto the welcoming farmer's porch and into a bright, open living, dining, and kitchen area with hardwood floors and air conditioning. A charming sunroom just off the di
Oak Bluffs 8155
Contemporary Cape in Oak Bluffs- Nestled between the Lagoon Sailing Camp Park and Farm Neck Golf Club, this contemporary Cape offers comfort, space, a... Read More
Contemporary Cape in Oak Bluffs- Nestled between the Lagoon Sailing Camp Park and Farm Neck Golf Club, this contemporary Cape offers comfort, space, a... Read More
Waterfront six bedroom main and guest house in a lovely sought after Oak Bluffs association of Hart Haven. The main house is exquisitely and architecturally designed with two primary suites, a chef's Kitchen, open and sprawling dining and living spaces all on the main level with peaceful water views of Farm Pond and a distance view of the Atlantic
Oak Bluffs 807
Waterfront six bedroom main and guest house in a lovely sought after Oak Bluffs association of Hart Haven. The main house is exquisitely and architect... Read More
Waterfront six bedroom main and guest house in a lovely sought after Oak Bluffs association of Hart Haven. The main house is exquisitely and architect... Read More
Don't miss out on this amazing vacation opportunity on Martha's Vineyard! You can relax in the comfortable living room and enjoy the beautiful view through the French doors that open to the patio area. The patio features a large lounge area and outdoor dining, as well as a grilling area poolside. The primary suite is conveniently located near the p
Oak Bluffs 8141
Don't miss out on this amazing vacation opportunity on Martha's Vineyard! You can relax in the comfortable living room and enjoy the beautiful view th... Read More
Don't miss out on this amazing vacation opportunity on Martha's Vineyard! You can relax in the comfortable living room and enjoy the beautiful view th... Read More
Lovely Oak Bluffs home in a private location with association access to Sengekontacket Pond. Two en suite bedrooms, a king on the first floor and a queen on the second. The remaining second-floor bedroom with twin beds has access to the hall bath, making it semi-private. Hot tub and game room with ping pong table and additional sleeping for tena
Oak Bluffs 814
Lovely Oak Bluffs home in a private location with association access to Sengekontacket Pond. Two en suite bedrooms, a king on the first floor and a q... Read More
Lovely Oak Bluffs home in a private location with association access to Sengekontacket Pond. Two en suite bedrooms, a king on the first floor and a q... Read More
A relaxing vacation awaits at this modern home overlooking the Lagoon. Tucked off of Barnes Road, the open concept layout offers stunning waterviews from the living, kitchen and dining areas, opening to a large outdoor deck. There is an ensuite bedroom on the main level and three additional bedrooms on the lower level as well as a media room with 6
Oak Bluffs 8104
A relaxing vacation awaits at this modern home overlooking the Lagoon. Tucked off of Barnes Road, the open concept layout offers stunning waterviews f... Read More
A relaxing vacation awaits at this modern home overlooking the Lagoon. Tucked off of Barnes Road, the open concept layout offers stunning waterviews f... Read More
Luxurious waterfront four bedroom , all private bathrooms, fully air conditioned, by their own individual high efficiency ductless mini-split units, beach house with state of the art kitchen, gorgeous and comfortable furnishings throughout, fabulous decking to outdoor entertaining overlooking the Lagoon Pond. Most every room in the house has a wate
Oak Bluffs 8151
Luxurious waterfront four bedroom , all private bathrooms, fully air conditioned, by their own individual high efficiency ductless mini-split units, b... Read More
Luxurious waterfront four bedroom , all private bathrooms, fully air conditioned, by their own individual high efficiency ductless mini-split units, b... Read More
Classic East Chop Victorian with all of the amenities that they didn't have back then! While away a summer afternoon sitting on the porch watching the boats go by and taking in the sea breeze! The porch is a showstopper, but step inside and let the vacation begin! Tastefully decorated to create a casual vibe: the kitchen is dressed with granite cou
Oak Bluffs 818
Classic East Chop Victorian with all of the amenities that they didn't have back then! While away a summer afternoon sitting on the porch watching the... Read More
Classic East Chop Victorian with all of the amenities that they didn't have back then! While away a summer afternoon sitting on the porch watching the... Read More
Charming Oak Bluffs Bungalow - Nestled just off Upper Circuit Avenue, this delightful two-bedroom, two-bathroom bungalow captures the heart of Oak Bluffs living. Ideally located for Illumination Night, fireworks, and all the village's vibrant attractions, the home offers both comfort and convenience.
Enjoy warm summer evenings on the cozy front por
Oak Bluffs 836
Charming Oak Bluffs Bungalow - Nestled just off Upper Circuit Avenue, this delightful two-bedroom, two-bathroom bungalow captures the heart of Oak Blu... Read More
Charming Oak Bluffs Bungalow - Nestled just off Upper Circuit Avenue, this delightful two-bedroom, two-bathroom bungalow captures the heart of Oak Blu... Read More
Comfortable and conveniently located just one mile from downtown and Inkwell Beach, this three-bedroom home is the perfect island getaway. The primary bedroom features a private half bath, while the two additional bedrooms share a full hall bath. Enjoy a bright living area, fully equipped kitchen, and spacious deck for outdoor dining and relaxation
Oak Bluffs 8128
Comfortable and conveniently located just one mile from downtown and Inkwell Beach, this three-bedroom home is the perfect island getaway. The primary... Read More
Comfortable and conveniently located just one mile from downtown and Inkwell Beach, this three-bedroom home is the perfect island getaway. The primary... 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
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