Oak Bluffs Vacation Homes

Compare 45 vacation rentals.
USA > Massachusetts > Oak Bluffs

Make Oak Bluffs your next getaway

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, cottages, studios, and more

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House rentals

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Cottages

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Studios

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Popular amenities for Oak Bluffs vacation rentals

Popular
Dog-friendly Hot tub Internet
The Rootskeller
4 Bedroom | 2 Bath | Sleeps 7 (5 Adults Max)

The Rootskeller - Oak Bluffs, MA

$303 avg / night
(excludes fees and taxes)
Sankofa Studio
0 Bedroom | 1 Bath | Sleeps 2

Sankofa Studio - Oak Bluffs, MA

$258 avg / night
(excludes fees and taxes)
4.91 (11)
Winthrop Cottage
3 Bedroom | 1 Bath | Sleeps 6

Winthrop Cottage - Oak Bluffs, MA

$323 avg / night
(excludes fees and taxes)
4.08 (39)
Oak Bluffs Cottage
3 Bedroom | 2.5 Bath | Sleeps 6

Oak Bluffs Cottage - Oak Bluffs, MA

$445 avg / night
(excludes fees and taxes)
4.28 (32)
Beach House
5 Bedroom | 2 Bath | Sleeps 12

Beach House - Oak Bluffs, MA

$883 avg / night
(excludes fees and taxes)

View 40 more homes

Recent Oak Bluffs guest reviews

This house was the perfect size, small property but a nice deck out back to relax on. Inside was clean, roomy and just the perfect place to relax after a day of roaming Oak Bluffs. It's a 2 minute drive to town or a 15 minute walk which was easy. All in all, I would stay here every visit if I could. Enjoy!
Jessica S. | Jun 2025
Location, accommodations, and cleanliness were excellent.
Tony W. | Jun 2025
We had 8 adults and a baby and the house was a perfect size for us - could easily accommodate more. Nice features and location. Several of the key amenities were missing/not working. The roofdeck firepit did not work which was disappointing in the cool evenings. The 12 beach chairs advertised were not there, nor beach towels. 3 of the bathroom towel racks/rings could not hold a towel without falling off. Kitchen tools were spare and no wine glasses in a house on Martha's Vineyard! The roofdeck grill was dirty from use but we bought a grill brush and did it ourselves. Only way to communicate issues was through chatbot with limited results - we ended up getting beach towels, but nothing else was addressed while we were there.
Frank C. | Jun 2025
Oak Bluffs vacation rental FAQ

Yes, 42 of our Oak Bluffs homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

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Yes. 146 of our Oak Bluffs vacation rentals have internet access, so you can stay connected throughout your trip.

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Some of the most popular amenities in our Oak Bluffs vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find the check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Oak Bluffs team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No problem, plans can change. For more information, please read our cancellation policy. If you have a Vacasa reservation for Oak Bluffs, log in to Trip Manager to explore the options available for your specific trip.

Book confidently. Stay comfortably.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
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Seamless check-in
Vacasa Guest Value Prop Icons 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.  

Oak Bluffs travel inspiration

The ultimate guide to a dog-friendly East Coast vacation