Oak Bluffs Vacation Rentals

Compare 1,067 available properties from 20 providers
Oak Bluffs

Find a rental that matches your criteria among the 1,049 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 10%.

Recommended Vacation Rentals in Oak Bluffs

Rent a vacation accommodation in Oak Bluffs: from $96 per night

Apartment ∙ 4 guests ∙ 2 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
from $429
VRBO
4.6
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Apartment ∙ 2 guests
Oak Bluffs, Dukes County, Massachusetts, United States
from $170
VRBO
5.0
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Apartment ∙ 6 guests ∙ 2 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
from $157
VRBO
4.9
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House ∙ 7 guests ∙ 2 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
from $247
VRBO
4.8
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Apartment ∙ 4 guests ∙ 2 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
from $425
VRBO
5.0
View deal
Apartment ∙ 6 guests ∙ 2 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
from $315
VRBO
4.5
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House ∙ 6 guests ∙ 3 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
from $550
VRBO
5.0
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House ∙ 4 guests ∙ 2 bedrooms
Vineyard Haven, Tisbury, Massachusetts, United States
from $137
VRBO
5.0
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House ∙ 2 guests ∙ 1 bedroom
Vineyard Haven, Tisbury, Massachusetts, United States
from $187
Booking.com
4.2
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Vacation Homes With Fishing Spots Nearby

Fishing
House ∙ 4 guests
Vineyard Haven, Tisbury, Massachusetts, United States
from $98
VRBO
4.8
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Fishing
House ∙ 10 guests ∙ 3 bedrooms
Vineyard Haven, Tisbury, Massachusetts, United States
from $100
VRBO
4.9
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Fishing
House ∙ 4 guests ∙ 2 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
from $471
VRBO
5.0
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Vacation Rentals With Fireplaces

Fireplace
House ∙ 5 guests ∙ 2 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
from $285
VRBO
4.5
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Fireplace
House ∙ 8 guests ∙ 5 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
from $453
VRBO
4.9
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Fireplace
House ∙ 10 guests ∙ 5 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
from $763
VRBO
4.8
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Apartments With Balconies or Patios

Balcony/Patio
House ∙ 6 guests ∙ 3 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
from $357
VRBO
5.0
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Balcony/Patio
House ∙ 7 guests ∙ 3 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
from $267
VRBO
4.6
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Balcony/Patio
House ∙ 5 guests ∙ 2 bedrooms
Vineyard Haven, Tisbury, Massachusetts, United States
from $46
VRBO
4.9
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Popular Rental Amenities in Oak Bluffs

  • Kitchen (1,013)
  • Internet (998)
  • TV (997)
  • No smoking (997)
  • Microwave (952)
  • AC (814)
  • No pets (800)
  • Grill (794)
  • Dishwasher (766)
  • Parking (721)
  • Washer (684)
  • Yard (387)
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."

Price and Availability Index in Oak Bluffs

Vacation Rental Price Information in Oak Bluffs

The graph shows average prices of rental prices in Oak Bluffs for the next twelve months. Prices in a week of July (7/27 - 8/3) go up to $550 per night, which is the highest average price in the next 12 months. Prices are more affordable in December (12/8 - 12/15).

Rental Availability Information in Oak Bluffs

Check out the graph above to find out how many accommodations are available in Oak Bluffs(in %). The week with the least available rentals is in August (8/10 - 8/17), with only 36% of the rentals available. The week with the most available rentals is in September (9/7 - 9/14), with 79% of the vacation rentals available.

The Weather in Oak Bluffs

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27°
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25°
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55°
37°
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48°
73°
55°
81°
64°
79°
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54°
64°
46°
54°
37°
48°
34°
Jan.
Feb.
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May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Check out our climate diagram to find the perfect month for your vacation. In the next 6 months, July will have higher average temperatures. Conversely, February is the coolest month in Oak Bluffs, with temperatures going under 24° The rainiest month is July while the driest month is August.

Accommodations in Oak Bluffs

Most of the accommodations (85.19%) 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 2,170 ft² and they cost, on average, $764 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 $310 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.

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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 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