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Oak Bluffs Rentals

Our Oak Bluffs rentals are the prime summer vacation destination in Martha's Vineyard. Its fun and active ambiance really opens up with the arrival of Memorial weekend and stays in full swing until Columbus weekend. It has historically been a summer destination dating back to the mid 1800’s when the camp ground cottages were developed as a Methodist summer retreat which actually started with camp sites and developed into the quaint, colorful gingerbread cottages that we see today.

For attractions near your Oak Bluff vacation rentals, visit the town center,  located on the harbor and has a high energy level with hundreds of boats coming and going. Circuit Avenue is the commercial heart of Oak Bluffs. It has ice cream and sunscreen, coffee stands and souvenir shops. It has Reliable Self-Serve Market, family owned and operated, and Giordano's Restaurant and Clam Bar, offering up family style meals since 1930. It has Back Door Doughnuts (on a summer's night, between 9 p.m. and 12:30 a.m., buy them fresh from the oven in the parking lot behind Reliable Market.). Circuit Avenue starts with the Flying Horses Carousel, the nation's oldest operating platform carousel and a National Historical Landmark owned by the Martha's Vineyard Preservation Trust and ends with the start of the Art District on the other end. Oak Bluffs also hosts the "summer” steamship authority terminal adding to its high summer foot traffic.

There are many residential areas outside of the downtown that offer quiet privacy for your summer vacation yet have easy access to downtown Oak Bluffs, Edgartown and Vineyard Haven. Contact us for more information about any of the Oak Bluffs rentals on our site.


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109 properties found

7253 Bed / 2.5 Bath / Sleeps 6

Oak Bluffs

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A unique 3 bedroom 2.5 bathroom home built in the round on East Chop Drive overlooking the East Chop Lighthouse. Yes, th...read more

80004 Bed / 1.5 Bath / Sleeps 8

Oak Bluffs

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This Victorian style gingerbread cottage is located in a great area in Oak Bluffs, easy walk to Ocean Park, Flying Horse...read more

80105 Bed / 3.0 Bath / Sleeps 10

Oak Bluffs

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Beautiful large traditional cottage in Oak Bluffs with full view of Nantucket Sound and Oak Bluffs Harbor. Close to town...read more

80113 Bed / 1.5 Bath / Sleeps 6

Oak Bluffs

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Sparkling Vineyard cottage has the fresh airy updates with painted white ship lap for wall decor, hardwoods and stainles...read more

80122 Bed / 1.5 Bath / Sleeps 6

Oak Bluffs

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The tranquil and much sought after neighborhood of Sengekontacket Pond is yours in this two bedroom, two bath condo with...read more

80146 Bed / 2.5 Bath / Sleeps 14

Oak Bluffs

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This 6 bedroom Oak Bluffs Gingerbread home is well appointed with a grand open floor plan, chefs kitchen, formal dining,...read more

80164 Bed / 5.5 Bath / Sleeps 8

Oak Bluffs

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A stoic restoration reveals a truly stunning home in Ocean Park - with a gourmet kitchen adorned with antique accents, a...read more

80176 Bed / 6.5 Bath / Sleeps 14

Oak Bluffs

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ONLY A FIVE MINUTE WALK TO OAK BLUFFS CENTER! On the outskirts of the infamous Oak Bluffs ginger bread cottages, this ho...read more

80182 Bed / 2.0 Bath / Sleeps 4

Oak Bluffs

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Modern two bedroom home just steps from everything you want to do in Oak Bluffs. Classic post and beam design packs a lo...read more

80194 Bed / 4.5 Bath / Sleeps 10

Oak Bluffs

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ONLY A FIVE MINUTE WALK TO OAK BLUFFS CENTER! On the outskirts of the infamous Oak Bluffs ginger bread cottages, this ho...read more