Oak Bluffs Vacation Homes

Compare 48 vacation rentals.
1 Guest
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, apartments, cottages, and more

housing_type_house.jpg

House rentals

View 45 House rentals
housing_type_apartment.jpg

Apartments

View 1 Apartments
housing_type_cottage.jpg

Cottages

View 1 Cottages

Oak Bluffs vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Garage Suite
1 Bed | 1 Bath | Sleeps 2

Garage Suite - Oak Bluffs, MA

$459 avg / night
(excludes fees and taxes)
5.0 (1)
Family Getaway
4 Bed | 4.5 Bath | Sleeps 8

Family Getaway - Oak Bluffs, MA

$975 avg / night
(excludes fees and taxes)
Island Getaway
2 Bed | 2 Bath | Sleeps 4

Island Getaway - Oak Bluffs, MA

$467 avg / night
(excludes fees and taxes)
3.81 (27)
The Rootskeller
4 Bed | 2 Bath | Sleeps 7 (5 Adults Max)

The Rootskeller - Oak Bluffs, MA

$404 avg / night
(excludes fees and taxes)
Winthrop Cottage
3 Bed | 1 Bath | Sleeps 6

Winthrop Cottage - Oak Bluffs, MA

$485 avg / night
(excludes fees and taxes)
4.12 (42)

View 43 more homes

Recent Oak Bluffs vacation rental reviews

We LOVED our stay in your beautiful home. The location was the best and the home was clean and cozy. The kitchen and bathrooms were great and we were able to cook some meals for our large family. The space was perfect for our family and we loved sitting out on the porch and taking multiple walks a day to the park and town. We would love to come back next year. Thank for sharing your home with us!
Katherine G. | Jul 2025
The home was the perfect size for a couple that needed a base while traveling the island. Bed was comfortable. The house is off a main road but traffic noise is very minimal. Shower is great. Patio was a good touch to have a morning coffee. AC is good too
Arnulfo Q. | Jul 2025
We really enjoyed our stay at this home even with two toddlers. The backyard was very comfortable and the house was in a great location to anything we wanted to go see or do.
Lauren A. | Jul 2025
Oak Bluffs Frequently Asked Questions

Yes, 10 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. 153 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.  

Oak Bluffs travel inspiration

The ultimate guide to a dog-friendly East Coast vacation

 

Su
Mo
Tu
We
Th
Fr
Sa
29
30
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
2