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!
130 properties available
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
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
Come experience Oak Bluffs in this quintessential five bedroom gingerbread cottage reminiscent of times gone by. Just a stroll down the street to Inkwell Beach or into town. The five bedrooms are located on the second floor and share two bathrooms. There is an additional half bath and an outdoor shower. Your favorite part of your vacation will be
Oak Bluffs 833
Come experience Oak Bluffs in this quintessential five bedroom gingerbread cottage reminiscent of times gone by. Just a stroll down the street to Inkw... Read More
Come experience Oak Bluffs in this quintessential five bedroom gingerbread cottage reminiscent of times gone by. Just a stroll down the street to Inkw... Read More
Pirate's Reef is a beautifully decorated residence that offers five spacious bedrooms (two primary suites!) with four and a half bathrooms and accommodates up to twelve guests. This is the PERFECT vacation home! It's nestled behind the historic Shearer Cottage on a quiet lane in East Chop, just minutes away from all the charm and activities that Oa
Oak Bluffs 8129
Pirate's Reef is a beautifully decorated residence that offers five spacious bedrooms (two primary suites!) with four and a half bathrooms and accommo... Read More
Pirate's Reef is a beautifully decorated residence that offers five spacious bedrooms (two primary suites!) with four and a half bathrooms and accommo... Read More
FERRY TICKETS AVAILABLE: 7/11 - 7/18, 7/25 - 8/1
Experience the charm of this inviting single-story rental home, the perfect retreat for your next vacation. Thoughtfully furnished with brand-new décor and modernized bathrooms, this cozy getaway ensures a comfortable and relaxing stay. The finished basement offers an additional TV room and games for
Oak Bluffs 8161
FERRY TICKETS AVAILABLE: 7/11 - 7/18, 7/25 - 8/1 Experience the charm of this inviting single-story rental home, the perfect retreat for your next vac... Read More
FERRY TICKETS AVAILABLE: 7/11 - 7/18, 7/25 - 8/1 Experience the charm of this inviting single-story rental home, the perfect retreat for your next vac... Read More
This comfortable three-bedroom vacation home is centrally located along the bike path and is approximately four miles from the charming towns and beautiful beaches of Edgartown, Oak Bluffs, and Vineyard Haven. The house features cozy furnishings and lovely wood floors on both the first and second levels.
Amenities include high-speed wireless intern
Oak Bluffs 860
This comfortable three-bedroom vacation home is centrally located along the bike path and is approximately four miles from the charming towns and beau... Read More
This comfortable three-bedroom vacation home is centrally located along the bike path and is approximately four miles from the charming towns and beau... Read More
Designed by renowned architect Patrick Ahearn, this house offers a contemporary interpretation of a Martha's Vineyard Cape. Evoking the grandeur of an equestrian estate, this six-bedroom, nine-bath home is perched on a hill, overlooking a pond and situated on nearly four acres in the Preserve. The impeccably designed interiors create a sense of pla
Oak Bluffs 8168
Designed by renowned architect Patrick Ahearn, this house offers a contemporary interpretation of a Martha's Vineyard Cape. Evoking the grandeur of an... Read More
Designed by renowned architect Patrick Ahearn, this house offers a contemporary interpretation of a Martha's Vineyard Cape. Evoking the grandeur of an... 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 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
This charming waterfront two story Cape sits atop the Lagoon bluffs. Boasts spectacular sunsets and panoramic waterfront views of Lagoon, outer Vineyard Haven Harbor and Cape Cod from the patios, living room, dining room and two upstairs bedrooms. Stairs down to private beach. You are just minutes to the center of Oak Bluffs village. It truly is a
Oak Bluffs 805
This charming waterfront two story Cape sits atop the Lagoon bluffs. Boasts spectacular sunsets and panoramic waterfront views of Lagoon, outer Vineya... Read More
This charming waterfront two story Cape sits atop the Lagoon bluffs. Boasts spectacular sunsets and panoramic waterfront views of Lagoon, outer Vineya... 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
Prepare to be mesmerized by the awe-inspiring sunsets visible from the large wraparound deck and several rooms of this immaculate Oak Bluffs home. Boasting tasteful and charming decor, this spacious property provides ample space for the entire family, including a bonus TV room on the lower level.
The high-end kitchen is customized with top-of-the-l
Oak Bluffs 811
Prepare to be mesmerized by the awe-inspiring sunsets visible from the large wraparound deck and several rooms of this immaculate Oak Bluffs home. Boa... Read More
Prepare to be mesmerized by the awe-inspiring sunsets visible from the large wraparound deck and several rooms of this immaculate Oak Bluffs home. Boa... 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
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