Oak Bluffs Vacation Rentals

Compare 1,363 available properties from 20 providers
Oak Bluffs
Save up to 47%

Best Vacation Home Deals in Oak Bluffs

-47%
e.g. 3/23 - 3/30
House ∙ 6 guests ∙ 3 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
from $177 $334
HomeAway
3.4
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-36%
e.g. 10/6 - 10/13
House ∙ 6 guests ∙ 3 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
from $346 $539
HomeAway
5.0
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-22%
e.g. 9/29 - 10/6
House ∙ 5 guests ∙ 3 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
from $347 $447
VRBO
View deal

Find a rental that matches your criteria among the 1,363 welcoming properties from 20 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 47%.

Recommended Vacation Rentals in Oak Bluffs

Rent a vacation accommodation in Oak Bluffs: from $99 per night

Apartment ∙ 4 guests ∙ 2 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
from $342
VRBO
5.0
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House ∙ 8 guests ∙ 2 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
from $236
VRBO
4.0
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Apartment ∙ 4 guests ∙ 1 bedroom
Oak Bluffs, Dukes County, Massachusetts, United States
from $228
VRBO
4.9
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House ∙ 4 guests ∙ 2 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
from $467
VRBO
5.0
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House ∙ 6 guests ∙ 4 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
from $228
VRBO
5.0
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House ∙ 5 guests ∙ 2 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
from $402
VRBO
4.7
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House ∙ 4 guests ∙ 1 bedroom
Oak Bluffs, Dukes County, Massachusetts, United States
from $318
VRBO
4.9
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Apartment ∙ 2 guests
Oak Bluffs, Dukes County, Massachusetts, United States
from $180
Booking.com
4.3
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Vacation Homes With Fishing Spots Nearby

Fishing
House ∙ 4 guests
Oak Bluffs, Dukes County, Massachusetts, United States
from $98
VRBO
4.7
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Fishing
House ∙ 6 guests ∙ 3 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
from $333
HomeAway
5.0
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Fishing
Apartment ∙ 5 guests ∙ 3 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
from $401
HomeAway
5.0
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Fishing
Apartment ∙ 4 guests ∙ 2 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
from $349
HomeAway
5.0
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Vacation Rentals With a Fireplace

Fireplace
House ∙ 7 guests ∙ 3 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
from $451
VRBO
5.0
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Fireplace
House ∙ 6 guests ∙ 3 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
from $436
HomeAway
5.0
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Fireplace
House ∙ 4 guests ∙ 2 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
from $249
VRBO
5.0
View deal
Fireplace
House ∙ 9 guests ∙ 4 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
from $250
HomeAway
4.9
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Apartments With a Balcony or Patio

Balcony/Patio
House ∙ 3 guests ∙ 1 bedroom
Oak Bluffs, Dukes County, Massachusetts, United States
from $283
VRBO
5.0
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Balcony/Patio
House ∙ 5 guests ∙ 2 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
from $163
VRBO
4.9
View deal
Balcony/Patio
Apartment ∙ 5 guests ∙ 2 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
from $132
VRBO
5.0
View deal
Balcony/Patio
House ∙ 4 guests ∙ 2 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
from $258
VRBO
5.0
View deal
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Popular Rental Amenities in Oak Bluffs

  • No smoking (1,250)
  • Internet (1,246)
  • TV (1,241)
  • Kitchen (1,219)
  • Microwave (1,128)
  • Grill (1,091)
  • AC (996)
  • Parking (947)
  • Dishwasher (945)
  • No pets (927)
  • Washer (855)
  • Yard (531)
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 want a rental with a sauna or you enjoy soaking in the hot tub. There are just 3 listed properties providing "saunas" and 18 properties providing "Jacuzzis."

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 (83.98%) 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 2,210 ft² and they cost, on average, $691 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 $338 a night for an area of 900 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.

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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 300 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