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
This charming, single-story cottage blends island simplicity with comfort. Though modest in size, the home maximizes its layout with warm, thoughtfully arranged spaces. At its heart is a welcoming living and dining area that opens directly onto the front porch, creating an easy indoor-outdoor flow. Two bedrooms share an adjoining bath, and a third
Oak Bluffs 862
This charming, single-story cottage blends island simplicity with comfort. Though modest in size, the home maximizes its layout with warm, thoughtfull... Read More
This charming, single-story cottage blends island simplicity with comfort. Though modest in size, the home maximizes its layout with warm, thoughtfull... 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
This six bedroom Oak Bluffs Gingerbread home is well appointed with a grand open floor plan, chef's kitchen, formal dining, front living space, spilling into a cordial verandah where you will view many beautiful sunrises and sights of the Atlantic Ocean. You are minutes to the beach, village, tennis, basketball, and the bike path. Inside you will f
Oak Bluffs 8014
This six bedroom Oak Bluffs Gingerbread home is well appointed with a grand open floor plan, chef's kitchen, formal dining, front living space, spilli... Read More
This six bedroom Oak Bluffs Gingerbread home is well appointed with a grand open floor plan, chef's kitchen, formal dining, front living space, spilli... Read More
This charming three-bedroom home is thoughtfully equipped with everything you need for the perfect home-away-from-home experience. Featuring hardwood floors, a beautifully updated kitchen with granite countertops, and plenty of inviting spaces for family and friends to relax and unwind, this property offers comfort and style throughout. All three b
Oak Bluffs 828
This charming three-bedroom home is thoughtfully equipped with everything you need for the perfect home-away-from-home experience. Featuring hardwood ... Read More
This charming three-bedroom home is thoughtfully equipped with everything you need for the perfect home-away-from-home experience. Featuring hardwood ... 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
Enjoy this sprawling property packed with activities for all, and fantastic views of the ocean. This home includes a spacious main house, guest house, and oversized deck, perfect for entertaining, grilling and memorable evenings. The nearby guest house includes a king bed, kitchenette, and full bath. This home includes many amenities for all to enj
Oak Bluffs 812
Enjoy this sprawling property packed with activities for all, and fantastic views of the ocean. This home includes a spacious main house, guest house,... Read More
Enjoy this sprawling property packed with activities for all, and fantastic views of the ocean. This home includes a spacious main house, guest house,... Read More
This rental house is a contemporary and inviting home that combines modern amenities with a cozy Cape feel. The spacious and open concept living area features a wall of windows that overlooks the backyard, allowing plenty of natural light to fill the space. The chef's kitchen is a highlight of the home with a massive 13-foot island that is perfect
Oak Bluffs 840
This rental house is a contemporary and inviting home that combines modern amenities with a cozy Cape feel. The spacious and open concept living area ... Read More
This rental house is a contemporary and inviting home that combines modern amenities with a cozy Cape feel. The spacious and open concept living area ... 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
Charming Oak Bluffs Cottage- This delightful three-bedroom cottage offers the perfect blend of comfort and convenience for your Martha's Vineyard stay. The first floor features an open-concept living, kitchen, and dining area—ideal for gathering. Also on the main level is an en-suite bedroom and an additional full bathroom with laundry facilities.
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Oak Bluffs 8103
Charming Oak Bluffs Cottage- This delightful three-bedroom cottage offers the perfect blend of comfort and convenience for your Martha's Vineyard stay... Read More
Charming Oak Bluffs Cottage- This delightful three-bedroom cottage offers the perfect blend of comfort and convenience for your Martha's Vineyard stay... 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
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
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
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