Oak Bluffs Vacation Rentals

Compare 1,290 available properties from 18 providers
Oak Bluffs
Save up to 45%

Best vacation home deals in Oak Bluffs

$301
from $236
-22%
Apartment
5 2
Oak Bluffs, Dukes County, Massachusetts, United States
Found on
VRBO
$358
from $277
-23%
House
4 2
Oak Bluffs, Dukes County, Massachusetts, United States
Found on
VRBO
$455
from $251
-45%
1500 ft² House
6 4
Vineyard Haven, Tisbury, Massachusetts, United States
Found on
VRBO

Find a rental that matches your criteria among the 1,290 welcoming properties from 18 vacation rental websites in Oak Bluffs. Every one of the accommodations from the different providers are immediately compared by the search engine, allowing you to save up to 45%.

Recommended vacation rentals in Oak Bluffs

Rent a vacation accommodation in Oak Bluffs: from $90 per night

$247
from $125
-49%
House
2 1
Vineyard Haven, Tisbury, Massachusetts, United States
4.4
"Outstanding" 10 reviews
Found on VRBO
$400
from $175
-56%
830 ft² House
4 2
Vineyard Haven, Tisbury, Massachusetts, United States
4.1
"Very good" 11 reviews
Found on VRBO
from $372
1000 ft² House
6 2
Oak Bluffs, Dukes County, Massachusetts, United States
4.4
"Outstanding" 10 reviews
Found on VRBO
from $212
House
6 1
Oak Bluffs, Dukes County, Massachusetts, United States
4.3
"Outstanding" 180 reviews
Found on Booking.com
from $235
Apartment
2
Oak Bluffs, Dukes County, Massachusetts, United States
5.0
"Excellent" 6 reviews
Found on VRBO
$212
from $156
-27%
800 ft² House
6 2
Vineyard Haven, Tisbury, Massachusetts, United States
4.5
"Excellent" 21 reviews
Found on VRBO
$552
from $447
-19%
Apartment
5 2
Oak Bluffs, Dukes County, Massachusetts, United States
5.0
"Excellent" 12 reviews
Found on VRBO
from $205
1190 ft² Apartment
6 2
Oak Bluffs, Dukes County, Massachusetts, United States
5.0
"Excellent" 2 reviews
Found on VRBO
See all offers

  Vacation homes with fishing spots nearby

from $564
1100 ft² Apartment
5 3
Oak Bluffs, Dukes County, Massachusetts, United States
5.0
"Excellent" 2 reviews
Found on VRBO
$614
from $436
-29%
1670 ft² House
6 3
Oak Bluffs, Dukes County, Massachusetts, United States
5.0
"Excellent" 11 reviews
Found on VRBO
from $248
800 ft² Apartment
5 2
Oak Bluffs, Dukes County, Massachusetts, United States
5.0
"Excellent" 141 reviews
Found on VRBO
from $472
House
4 2
Oak Bluffs, Dukes County, Massachusetts, United States
5.0
"Excellent" 2 reviews
Found on VRBO
See all offers

  Vacation rentals with a fireplace

$441
from $193
-56%
1850 ft² House
6 3
Vineyard Haven, Tisbury, Massachusetts, United States
4.0
"Very good" 11 reviews
Found on VRBO
$455
from $251
-45%
1500 ft² House
6 4
Vineyard Haven, Tisbury, Massachusetts, United States
4.6
"Excellent" 15 reviews
Found on VRBO
from $286
1400 ft² House
5 2
Oak Bluffs, Dukes County, Massachusetts, United States
4.6
"Excellent" 5 reviews
Found on VRBO
from $316
1350 ft² House
6 4
Vineyard Haven, Tisbury, Massachusetts, United States
4.8
"Excellent" 9 reviews
Found on VRBO
See all offers

  Apartments with a balcony or patio

from $353
1700 ft² House
5 2
Vineyard Haven, Tisbury, Massachusetts, United States
5.0
"Excellent" 1 review
Found on VRBO
$454
from $258
-43%
590 ft² Apartment
4 1
Oak Bluffs, Dukes County, Massachusetts, United States
4.9
"Excellent" 30 reviews
Found on VRBO
$633
from $159
-75%
1560 ft² House
6 3
Vineyard Haven, Tisbury, Massachusetts, United States
4.4
"Outstanding" 18 reviews
Found on VRBO
from $350
1500 ft² House
6 3
Oak Bluffs, Dukes County, Massachusetts, United States
4.5
"Excellent" 2 reviews
Found on VRBO
See all offers

Popular rental amenities in Oak Bluffs

  • Kitchen (1,205)
  • TV (1,197)
  • Internet (1,194)
  • No smoking (1,174)
  • Microwave (1,122)
  • Grill (1,093)
  • AC (957)
  • Dishwasher (933)
  • No pets (895)
  • Parking (842)
  • Washer (829)
  • Fishing (524)
Properties can be selected based on the amenities they offer. Above, you can see the number of rentals that offer a specific feature in Oak Bluffs. HomeToGo's data reveals that "TVs" and "internet" are the most frequently offered amenities in Oak Bluffs. Plan your vacation in advance if you need a crib for your baby or you want to sweat it out in a sauna. There are just 0 listed properties providing "cribs" and 8 properties providing "saunas."

The weather in Oak Bluffs

41°
27°
39°
25°
46°
28°
55°
37°
66°
48°
73°
55°
81°
64°
79°
61°
75°
54°
64°
46°
54°
37°
48°
34°
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

The above is a climate diagram for Oak Bluffs. The highest average temperatures are in the month of July. February is the coolest month, with average minimal temperature reaching 24°. It may rain 16 days in January while it typically rains only 9 days in August.

Most of the accommodations (86.59%) in Oak Bluffs are house rentals. They are the most typical properties in this destination. In addition, the median size of house rentals in Oak Bluffs is 2,220 ft² and they cost, on average, $652 a night. Furthermore, if you are going in a group of 8, house rentals are an excellent type of accommodation in Oak Bluffs, as they usually welcome this exact group size. If you would like to rent something else, you can compare many other available options, such as apartment rentals, which are the second most popular type of accommodation in Oak Bluffs. Our data shows that the median price of apartment rentals is $326 a night for an area of 880 ft².

Enjoy whimsical island charm with a vacation home in Oak Bluffs

Oak Bluffs is located on the island of Martha's Vineyard, a seven-mile ferry ride from Cape Cod. Rent one of Oak Bluffs' famous "gingerbread" cottages, adorned with intricate scrollwork and painted with bright, whimsical colors. Traditional Cape Cod-style homes are also available, as well as luxury condos.

Show all 1,290 properties
Food & Drinks

From clambakes to fine dining

Dine at the Black Dog Tavern, a favorite of American presidents Bill Clinton and Barak Obama. The Vineyard's most famous eating establishment also sells clothing and souvenirs with the black labrador logo.

While the Vineyard has many fine dining options, it is best known for homemade ice cream, fudge and clambakes on the beach. The clambake tradition goes back to the Wampanoag people, who steamed seafood over heated stones and seaweed.

Family Activities

Fun for kids of all ages

Go for a whirl on the Flying Horses Carousel, the oldest carousel in the country, or pet an alpaca at the Island Alpaca Company. Nip N' Tuck Farm also has farm animals, as well as buggy and hay rides.

Sign up for an interactive Pirate Adventure, where kids dress up as pirates, board a custom-built pirate ship and search for sunken treasure in Oak Bluffs Harbor. Or embark on a Nature Quest at Felix Neck Wildlife Sanctuary, and discover all about local animals, plants and their habitats.

Local Attractions

Explore the spectacular island setting

One of the best ways to explore the island is by bike. The entire island is criss-crossed with well-maintained paths, which are also open to pedestrians. Rent kayaks, paddle boards, or book a sunset sailboat cruise or fishing charter.

Take a dip in the calm waters of Oak Bluffs Town Beach or walk along the thundering surf on the island's south shore. Visit the multi-colored Gay Head Cliffs in nearby Aquinnah, and the historic Gay Head Lighthouse.

We compare more than 250 providers, including:

Booking.com Vacation Rentals in Oak Bluffs VRBO Vacation Rentals in Oak Bluffs HomeAway Vacation Rentals in Oak Bluffs TripAdvisor Vacation Rentals in Oak Bluffs VacationRentals.com Vacation Rentals in Oak Bluffs HouseTrip Vacation Rentals in Oak Bluffs FlipKey Vacation Rentals in Oak Bluffs Wimdu Vacation Rentals in Oak Bluffs 9flats.com Vacation Rentals in Oak Bluffs VaycayHero Vacation Rentals in Oak Bluffs PerfectPlaces.com Vacation Rentals in Oak Bluffs Homestay.com Vacation Rentals in Oak Bluffs only-apartments Vacation Rentals in Oak Bluffs Interhome Vacation Rentals in Oak Bluffs Bedycasa Vacation Rentals in Oak Bluffs Novasol Vacation Rentals in Oak Bluffs HomeEscape Vacation Rentals in Oak Bluffs

Vacation destinations near Oak Bluffs