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
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
Prime Oak Bluffs location in a serene setting. This home has plenty of room to spread out and enjoy your vacation. The main level has a generous and spacious kitchen that opens to both the dining and living areas. Off of the dining area is a lovely screened porch, perfect for that extra space. There is also a bedroom and full bath, along with laund
Oak Bluffs 802
Prime Oak Bluffs location in a serene setting. This home has plenty of room to spread out and enjoy your vacation. The main level has a generous and s... Read More
Prime Oak Bluffs location in a serene setting. This home has plenty of room to spread out and enjoy your vacation. The main level has a generous and s... 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
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
Nestled on 1.5 private, wooded acres in Hidden Cove, this beautifully appointed multi-level home offers an ideal blend of tranquility and space for gathering. The open living and dining areas create a welcoming atmosphere, while the thoughtful layout provides quiet retreats for guests. The home sleeps seven and features three bedrooms and four and
Oak Bluffs 8013
Nestled on 1.5 private, wooded acres in Hidden Cove, this beautifully appointed multi-level home offers an ideal blend of tranquility and space for ga... Read More
Nestled on 1.5 private, wooded acres in Hidden Cove, this beautifully appointed multi-level home offers an ideal blend of tranquility and space for ga... 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
A well-built three-bedroom custom cape is just minutes from the village of Oak Bluffs. As you enter this home, you are graced with cathedral ceilings equipped with ceiling fans, a flat screen TV, and inviting sofas to enjoy the comforts of this home. The first floor has a well-equipped galley-style kitchen with three stools at the peninsula for tho
Oak Bluffs 821
A well-built three-bedroom custom cape is just minutes from the village of Oak Bluffs. As you enter this home, you are graced with cathedral ceilings ... Read More
A well-built three-bedroom custom cape is just minutes from the village of Oak Bluffs. As you enter this home, you are graced with cathedral ceilings ... Read More
All the charm of Oak Bluffs in an updated, clean and comfortable gingerbread cottage. This house is perfect for families with children. The neighborhood is quiet and relaxing with all of the action just a stroll away. Ocean Park, the beach and Circuit Avenue are no more than two short blocks. Everyone can do their own thing. Depart out the front do
Oak Bluffs 815
All the charm of Oak Bluffs in an updated, clean and comfortable gingerbread cottage. This house is perfect for families with children. The neighborho... Read More
All the charm of Oak Bluffs in an updated, clean and comfortable gingerbread cottage. This house is perfect for families with children. The neighborho... 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
A classic East Chop summer house, featuring multiple bedrooms and situated just minutes away center of town. Step outside to enjoy a generous deck and patio areas, ideal for warm summer evenings. Inside, you'll discover a cozy living area, dining space, and spacious kitchen. The first floor also includes a twin bedroom and a full bathroom. Upstairs
Oak Bluffs 8056
A classic East Chop summer house, featuring multiple bedrooms and situated just minutes away center of town. Step outside to enjoy a generous deck and... Read More
A classic East Chop summer house, featuring multiple bedrooms and situated just minutes away center of town. Step outside to enjoy a generous deck and... Read More
A beautiful downtown cottage which has been exquisitely renovated in a way that reflects the charming history, while simultaneously exemplifying modern taste. Painted wood floors, custom built-ins, brand new everything -- and a stunning outdoor space -- the quality of finish work is meticulous and the end result is just divine. Offering three bedr
Oak Bluffs 8815
A beautiful downtown cottage which has been exquisitely renovated in a way that reflects the charming history, while simultaneously exemplifying moder... Read More
A beautiful downtown cottage which has been exquisitely renovated in a way that reflects the charming history, while simultaneously exemplifying moder... Read More
This newly renovated home located in Hidden Cove in Oak Bluffs sleeps 9 with 4 bedrooms and 2.5 bathrooms. The modern kitchen equipped with stainless steel appliances and a larger island provides ample space for cooking and dining. The large indoor living area and outdoor patio offers space to share with the whole group. The second story has 2 bedr
Oak Bluffs 8024
This newly renovated home located in Hidden Cove in Oak Bluffs sleeps 9 with 4 bedrooms and 2.5 bathrooms. The modern kitchen equipped with stainless ... Read More
This newly renovated home located in Hidden Cove in Oak Bluffs sleeps 9 with 4 bedrooms and 2.5 bathrooms. The modern kitchen equipped with stainless ... Read More
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