Oak Bluffs Vacation Homes

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Make Oak Bluffs your next getaway—choose from 76 great vacation rentals

Beautiful beaches, quaint shops, and cozy restaurants make a getaway to one of our Oaks Bluffs vacation rentals on Martha's Vineyard a can't-miss Massachusetts experience.

Explore Oak Bluffs house rentals, studios, condo rentals, and more


House rentals

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Condo rentals

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Oak Bluffs vacation rentals for every getaway

Dog-friendly Hot tub Internet
Flamingo House 3D Tour
2 Bed | 1 Bath | Sleeps 4

Flamingo House - Oak Bluffs, MA

From $171
The Historic J.A. Norton House 3D Tour
4 Bed | 3 Bath | Sleeps 8

The Historic J.A. Norton House - Oak Bluffs, MA

From $1,188
Island Inn - 4B 3D Tour
0 Bed | 1 Bath | Sleeps 4

Island Inn - 4B - Oak Bluffs, MA

From $134
Winthrop Cottage 3D Tour
3 Bed | 1 Bath | Sleeps 6

Winthrop Cottage - Oak Bluffs, MA

From $191
Island Inn - 26F 3D Tour
0 Bed | 1 Bath | Sleeps 4

Island Inn - 26F - Oak Bluffs, MA

From $134

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Recent Oak Bluffs vacation rental reviews

Loved the spaciousness of the home for our large family gathering! We did not feel on top of each other during our stay!
Karen K. | Oct 2021
Great room set up and very convenient to many of the Island sites.
Steve S. | Oct 2021
I always love the Island Inn and this unit in particular. If you need to stay in and want to throw food together, there are the appliances you might want. One level living, parking almost at your door, perfect for mobility issues.
Margaret B. | Oct 2021

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning

Once a part of nearby Edgartown, Oak Bluffs became its own community in 1880 (it was formerly dubbed Cottage City). Named for the oak groves that grew along the bluffs overlooking Nantucket Sound, Oak Bluffs has long been a tourism stronghold. In the 19th century, tourists arrived from the mainland via steamer and shopped, danced, and swam to their hearts' content. Today, thousands of visitors head here each summer to swim in the warm waters of the Sound and to enjoy concerts, art festivals, and other activities throughout the season. 

Things to Do in Oak Bluffs, MA

Oak Bluffs boasts a wealth of attractions, the most notable being the Flying Horses Carousel. This Victorian-era merry-go-round, the nation's oldest, is a National Historic Landmark and delights children and adults from spring to fall. 

The Cottage Museum houses period furnishings and photos of the town from the 19th century. Tour the East Chop Lighthouse, a cast-iron lighthouse built in 1878 - the last lighthouse erected on the island. The Featherstone Center for the Arts features galleries and studios amid six beautiful acres. Enjoy a lecture series or admire the rotating exhibits. 

Outdoor Attractions in Oak Bluffs, MA

Oak Bluffs, like Edgartown, boasts a plethora of beautiful beaches and preserves. East Chop Beach is a small beach near the harbor with a great view of Nantucket Sound. Oak Bluffs Town Beach features calm water, perfect for novice swimmers and families. Joseph Sylvia Beach offers miles of soft sand and is a windsurfer's paradise. 

Hikers and bikers look no further than the beautiful parks, farms, and preserves in town. Sailing Camp Park features 15 acres of preserved land with great views of the lagoon. At 18 acres, Featherstone Farm boasts a network of tranquil wooded trails for wandering. Farm Pond Preserve displays a wealth of marshlands and woodland trails connected to Trade Wind Field Preserve; the latter offers nearly 72 lush acres of woodlands and fields. Pecoy Point Preserve affords visitors 17 acres of marsh and woodland, as well as trails along peaceful Sengekontacket Pond.

From scenic marshlands to quaint mom-and-pop shops and romantic eateries, our Oak Bluffs vacation homes offer the perfect home base for enjoying this charming town - and all of Martha's Vineyard.  

Discover Oak Bluffs

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Photo credit: AR Pictures via Shutterstock