Oak Bluffs Vacation Homes

Compare 92 vacation rentals. Enter your trip dates to get started.
USA > Massachusetts > Oak Bluffs

Make Oak Bluffs your next getaway—choose from 92 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

View 37 House rentals

Studios

View 21 Studios
housing_type_condo.jpg

Condo rentals

View 18 Condo rentals

Oak Bluffs vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Island Inn - 25F
0 Bed | 1 Bath | Sleeps 4

Island Inn - 25F - Oak Bluffs, MA

$302 avg / night
Island Inn - 14D
0 Bed | 1 Bath | Sleeps 4

Island Inn - 14D - Oak Bluffs, MA

$318 avg / night
Island Inn - 43G
2 Bed | 1.5 Bath | Sleeps 6

Island Inn - 43G - Oak Bluffs, MA

$533 avg / night
Nautical Daze - Studio
0 Bed | 1 Bath | Sleeps 2

Nautical Daze - Studio - Oak Bluffs, MA

$286 avg / night
Island Inn - 37G
1 Bed | 1.5 Bath | Sleeps 4

Island Inn - 37G - Oak Bluffs, MA

$443 avg / night

View 87 more homes

Recent Oak Bluffs vacation rental reviews

Enjoyed our short stay here!
Keith R. | Oct 2022
Myrna B. | Oct 2022
We were 5 senior citizen women visiting MV for fun for the 1st time. This place was just as described and perfect for us. It was spotless, convenient, plenty of kitchen items, magical view. The 2 bedrooms downstairs & 3 bedrooms up stairs were all charming.
Eileen C. | Oct 2022
Oak Bluffs Frequently Asked Questions

Yes, 66 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).

Browse dog-friendly homes >

Yes. 187 of our Oak Bluffs vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


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 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 worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Oak Bluffs, log in to Trip Manager to see options available for your specific trip.

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

Pet-Friendly East Coast Vacations Your Dog Will Love

Photo credit: AR Pictures via Shutterstock