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
A classic Oak Bluffs Cottage recently renovated and refreshed, adding air conditioning, a large sunroom and an additional half bath to this already charming two-bedroom cottage overlooking Niantic Park. The new sunroom, complete with a gas log stove, flatscreen television and vinyl turntable with in-ceiling speakers, creates an opportunity to unwin
Oak Bluffs 8077
A classic Oak Bluffs Cottage recently renovated and refreshed, adding air conditioning, a large sunroom and an additional half bath to this already ch... Read More
A classic Oak Bluffs Cottage recently renovated and refreshed, adding air conditioning, a large sunroom and an additional half bath to this already ch... 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
Enjoy a wonderful vacation in this beautifully maintained and sun-filled retreat. Situated on a charming street near the lagoon and just about a mile from downtown Oak Bluffs, this home offers the perfect balance of relaxation and convenience. The home features modern amenities throughout, including an updated kitchen, central air conditioning and
Oak Bluffs 837
Enjoy a wonderful vacation in this beautifully maintained and sun-filled retreat. Situated on a charming street near the lagoon and just about a mile ... Read More
Enjoy a wonderful vacation in this beautifully maintained and sun-filled retreat. Situated on a charming street near the lagoon and just about a mile ... 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
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
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
This classic 3 bedroom Oak Bluffs home is perfect for relaxing, entertaining and spending quality time with family. All 3 of the bedrooms are on the Main Level and there is bonus living space and 2 Twin beds on the Lower Level. The kitchen, living, and dining spaces flow seamlessly from one area of the Main Level to the next and have access to the
Oak Bluffs 838
This classic 3 bedroom Oak Bluffs home is perfect for relaxing, entertaining and spending quality time with family. All 3 of the bedrooms are on the M... Read More
This classic 3 bedroom Oak Bluffs home is perfect for relaxing, entertaining and spending quality time with family. All 3 of the bedrooms are on the M... 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
Three bedroom, two bath home in Sengekontacket Association Community offers two tennis courts, a clubhouse on a spring fed freshwater pond and a saltwater dock with easy access to the Vineyard Sound. A king primary suite occupies the entire second floor with sitting area and its own private bath. The remaining two bedrooms grace the first floor wit
Oak Bluffs 839
Three bedroom, two bath home in Sengekontacket Association Community offers two tennis courts, a clubhouse on a spring fed freshwater pond and a saltw... Read More
Three bedroom, two bath home in Sengekontacket Association Community offers two tennis courts, a clubhouse on a spring fed freshwater pond and a saltw... Read More
Located in the desirable East Chop area of Oak Bluffs, just a short distance from town, this stunning waterfront 4-bedroom, 3-bath home has been beautifully renovated and thoughtfully updated throughout. Fully equipped with all new furnishings and amenities, this exceptional Island retreat offers breathtaking water views from almost every room.
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Oak Bluffs 8093
Located in the desirable East Chop area of Oak Bluffs, just a short distance from town, this stunning waterfront 4-bedroom, 3-bath home has been beaut... Read More
Located in the desirable East Chop area of Oak Bluffs, just a short distance from town, this stunning waterfront 4-bedroom, 3-bath home has been beaut... Read More
A gorgeous home in an incredible location! This six-bedroom home offers water views, central air conditioning and a divine location, directly across from Ocean Park. The best spot for the annual Oak Bluffs Fireworks and Grand Illumination, outfitted with all of the modern amenities you could need.
There are two living areas, both on the first flo
Oak Bluffs 825
A gorgeous home in an incredible location! This six-bedroom home offers water views, central air conditioning and a divine location, directly across f... Read More
A gorgeous home in an incredible location! This six-bedroom home offers water views, central air conditioning and a divine location, directly across f... Read More
This adorable two-bedroom, two-bath guest house is just a short distance from downtown Oak Bluffs and nearby beaches. Stroll along the harbor, enjoy dinner, browse the unique shops, or visit the Flying Horses carousel—the oldest in the country—and try your luck at catching the golden ring.
The home is tastefully decorated and fully equipped, featur
Oak Bluffs 8140
This adorable two-bedroom, two-bath guest house is just a short distance from downtown Oak Bluffs and nearby beaches. Stroll along the harbor, enjoy d... Read More
This adorable two-bedroom, two-bath guest house is just a short distance from downtown Oak Bluffs and nearby beaches. Stroll along the harbor, enjoy d... Read More
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