Oak Bluffs Vacation Homes

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Make Oak Bluffs your next getaway—choose from 75 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
Island Inn - 33G 3D Tour
1 Bedroom | 1.5 Bath | Sleeps 6

Island Inn - 33G - Oak Bluffs, MA

From $228
Island Inn - 11D 3D Tour
0 Bedroom | 1 Bath | Sleeps 4

Island Inn - 11D - Oak Bluffs, MA

From $117
Island Inn - 19D 3D Tour
0 Bedroom | 1 Bath | Sleeps 4

Island Inn - 19D - Oak Bluffs, MA

From $117
Island Inn - 1A 3D Tour
2 Bedroom | 1 Bath | Sleeps 6

Island Inn - 1A - Oak Bluffs, MA

From $152
Island Inn - 24F 3D Tour
0 Bedroom | 1 Bath | Sleeps 4

Island Inn - 24F - Oak Bluffs, MA

From $117

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Recent Oak Bluffs vacation rental reviews

Great place, very clean. A little far out from the center— (~1.5 miles) so we walked a bunch of times cuz it was hard getting an Uber. Otherwise had everything we needed.
Rachel P. | Sep 2021
We enjoyed our stay in Oak Bluffs, and the Sunny Side Up house was a large part of that. It was spacious, clean, and everyone enjoyed their time in MV.
Karen O. | Sep 2021
The outdoor deck was lovely especially since we had great weather. However, we were eight adults and would have liked eight chairs for the dining room and the outside deck table. When we arrived there were only 6 dinner plates and 2 side plates. Again , not enough. We did have Ruth bring us replacements and on the whole we all enjoyed our stay.
Virginia C. | Sep 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