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!
124 properties available
Located in the heart of Oak Bluffs, your vacation will be as action packed or relaxing as you want it to be! Roomy and comfortable, this home has space for friends and family throughout each floor. The common space is open with comfortable furnishings and a large kitchen. Generous bedrooms will ensure that you get good rest on vacation! All bedroom
Oak Bluffs 806
Located in the heart of Oak Bluffs, your vacation will be as action packed or relaxing as you want it to be! Roomy and comfortable, this home has spac... Read More
Located in the heart of Oak Bluffs, your vacation will be as action packed or relaxing as you want it to be! Roomy and comfortable, this home has spac... Read More
A jaw-dropping restoration of a classic Gingerbread Cottage by the ocean - melding a sophisticated bohemian style with the nostalgia of yesteryear.
The modern decor reflects an aesthetic that is masterfully California: refined and tailored - but not overly fussy. Sleek, sophisticated fixtures adorn clean and simple surfaces - wood vanities and bu
Oak Bluffs 834
A jaw-dropping restoration of a classic Gingerbread Cottage by the ocean - melding a sophisticated bohemian style with the nostalgia of yesteryear. ... Read More
A jaw-dropping restoration of a classic Gingerbread Cottage by the ocean - melding a sophisticated bohemian style with the nostalgia of yesteryear. ... Read More
Perfect location for your family beach getaway , just a short distance to the water, just a few blocks into town to enjoy the picturesque parks, boardwalk, harbor life, retail therapy, restaurants and the eclectic activity of the Oak Bluffs village. No need to bring your car, the ferry comes into Oak Bluffs during the summer season and this home i
Oak Bluffs 8023
Perfect location for your family beach getaway , just a short distance to the water, just a few blocks into town to enjoy the picturesque parks, board... Read More
Perfect location for your family beach getaway , just a short distance to the water, just a few blocks into town to enjoy the picturesque parks, board... Read More
This spacious Cape-style home is located in a quiet residential neighborhood in Oak Bluffs, just a short drive to town and an easy walk to the Lagoon—perfect for kayaking and enjoying beautiful sunset views. The home is clean and fully equipped, featuring a first-floor primary bedroom and a small office that offers a private retreat. Additional bed
Oak Bluffs 8178
This spacious Cape-style home is located in a quiet residential neighborhood in Oak Bluffs, just a short drive to town and an easy walk to the Lagoon—... Read More
This spacious Cape-style home is located in a quiet residential neighborhood in Oak Bluffs, just a short drive to town and an easy walk to the Lagoon—... Read More
This stunning property in Oak Bluffs has been completely renovated and features nine bedrooms. The main house includes six bedrooms, along with two separate guest quarters. One guest section is located on the first floor, offering two bedrooms, two full bathrooms, and air conditioning throughout. The second guest unit is on the second floor, provid
Oak Bluffs 8148
This stunning property in Oak Bluffs has been completely renovated and features nine bedrooms. The main house includes six bedrooms, along with two se... Read More
This stunning property in Oak Bluffs has been completely renovated and features nine bedrooms. The main house includes six bedrooms, along with two se... Read More
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 extra entertainment. Unwind on the welcoming bac
Oak Bluffs 8161
Experience the charm of this inviting single-story rental home, the perfect retreat for your next vacation. Thoughtfully furnished with brand-new déco... Read More
Experience the charm of this inviting single-story rental home, the perfect retreat for your next vacation. Thoughtfully furnished with brand-new déco... Read More
This beautifully appointed three-bedroom home offers comfort and convenience with central air-conditioning throughout. The main level features a spacious king en-suite bedroom, and a second en-suite bedroom with a queen bed. Upstairs, you'll find a private queen bedroom with an en suite powder room that opens to a lovely roof deck—perfect for relax
Oak Bluffs 8026
This beautifully appointed three-bedroom home offers comfort and convenience with central air-conditioning throughout. The main level features a spaci... Read More
This beautifully appointed three-bedroom home offers comfort and convenience with central air-conditioning throughout. The main level features a spaci... 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
This spacious and sunny three-bedroom Cape is perfectly located in Oak Bluffs, just a short distance from Circuit Avenue, the town beach, library, and playground—making it easy to enjoy all the island has to offer.
The open main level features a bright and comfortable floor plan with a large living area, dining space, and well-equipped kitchen, alo
Oak Bluffs 8811
This spacious and sunny three-bedroom Cape is perfectly located in Oak Bluffs, just a short distance from Circuit Avenue, the town beach, library, and... Read More
This spacious and sunny three-bedroom Cape is perfectly located in Oak Bluffs, just a short distance from Circuit Avenue, the town beach, library, and... Read More
This centrally air conditioned four bedroom traditional style home is located within the Bayes Hill neighborhood. A spacious, quiet and well maintained area in Oak Bluffs with beautiful curb appeal. This property has a well equipped kitchen, spacious living area, deck, and an area for those who need to work from home. There is an enclosed outdoor
Oak Bluffs 8101
This centrally air conditioned four bedroom traditional style home is located within the Bayes Hill neighborhood. A spacious, quiet and well maintai... Read More
This centrally air conditioned four bedroom traditional style home is located within the Bayes Hill neighborhood. A spacious, quiet and well maintai... Read More
Welcome to your perfect getaway in this beautifully renovated cottage in Oak Bluffs, Martha's Vineyard. This cottage features three bedrooms, making it an ideal spot for family vacations. There is a first floor bedroom and a full bath on the first floor. On the second floor there are two bedrooms and a half bath. Just steps from Inkwell Beach offer
Oak Bluffs 8139
Welcome to your perfect getaway in this beautifully renovated cottage in Oak Bluffs, Martha's Vineyard. This cottage features three bedrooms, making i... Read More
Welcome to your perfect getaway in this beautifully renovated cottage in Oak Bluffs, Martha's Vineyard. This cottage features three bedrooms, making i... Read More
A classically styled, expanded Cape in the Preserve in Oak Bluffs. Perched on a knoll overlooking the pond, this sprawling home includes a great room with vaulted ceilings, kitchen, living and dining area with French doors that open to an expansive patio and pool. Separate wings on each side of the great room house another living/sitting room and p
Oak Bluffs 8134
A classically styled, expanded Cape in the Preserve in Oak Bluffs. Perched on a knoll overlooking the pond, this sprawling home includes a great room ... Read More
A classically styled, expanded Cape in the Preserve in Oak Bluffs. Perched on a knoll overlooking the pond, this sprawling home includes a great room ... Read More
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