Oak Bluffs Vacation Rentals - HomeToGo base64Hash Oak Bluffs Vacation Rentals - HomeToGo

Oak Bluffs Vacation Rentals

Find 312 available offers from 8 partners
Oak Bluffs
Anytime
Guests

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Accommodation types
House
Bed & Breakfast
Other
Distance to center
Max. 1 mi
Max. 2 mi
Max. 3 mi
Rating
Outstanding: 4.5+
Very Good: 4+
Good: 3.5+
Save up to 66%

Best Vacation Home Deals in Oak Bluffs

House Oak Bluffs
Dec 25 - Jan 1
-66%
$1,406
$477 per night
House ∙ 8 guests ∙ 5 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
Free cancellation
Details
RedAwning
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House Oak Bluffs
Sep 24 - Oct 1
-16%
$329
$276 per night
House ∙ 5 guests ∙ 2 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
Details
WeNeedaVacation
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Condo Oak Bluffs
Jun 17 - Jun 24
-33%
$215
$143 per night
Condo ∙ 3 guests ∙ 1 bedroom
Oak Bluffs, Dukes County, Massachusetts, United States
Details
WeNeedaVacation
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Find a rental that matches your criteria among the 312 welcoming properties from 8 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 66%.

Recommended Vacation Rentals in Oak Bluffs

Find your perfect vacation rental in Oak Bluffs: from $129 per night

House Oak Bluffs
Nov 16 - Nov 23
$248 per night
House ∙ 4 guests ∙ 2 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
Free cancellation
Details
RedAwning
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House Oak Bluffs
Oct 24 - Oct 31
-66%
$1,406
$477 per night
House ∙ 8 guests ∙ 5 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
Free cancellation
Details
RedAwning
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House Oak Bluffs
Sep 11 - Sep 18
$93 per night
House ∙ 3 guests ∙ 1 bedroom
Oak Bluffs, Dukes County, Massachusetts, United States
Details
WeNeedaVacation
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House Oak Bluffs
Sep 24 - Oct 1
-16%
$329
$276 per night
House ∙ 5 guests ∙ 2 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
Details
WeNeedaVacation
View deal
Condo Oak Bluffs
Jun 17 - Jun 24
-33%
$215
$143 per night
Condo ∙ 3 guests ∙ 1 bedroom
Oak Bluffs, Dukes County, Massachusetts, United States
Details
WeNeedaVacation
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House Oak Bluffs
Apr 23 - Apr 30
-59%
$1,645
$676 per night
House ∙ 10 guests ∙ 4 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
Free cancellation
Details
RedAwning
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House Oak Bluffs
May 7 - May 14
-25%
$572
$429 per night
House ∙ 7 guests ∙ 4 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
Details
WeNeedaVacation
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House Oak Bluffs
Jun 18 - Jun 25
$500 per night
House ∙ 6 guests ∙ 5 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
Details
WeNeedaVacation
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House Oak Bluffs
Oct 2 - Oct 9
-25%
$286
$215 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0/5.0 "Excellent"
(3 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Details
WeNeedaVacation
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Vacation rentals and apartments with air conditioning

House Aircondition Oak Bluffs
Oct 30 - Nov 6
$237 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0/5.0 "Excellent"
(1 rating)
Oak Bluffs, Dukes County, Massachusetts, United States
Aircondition
Details
WeNeedaVacation
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House Aircondition Oak Bluffs
Oct 23 - Oct 30
$486 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0/5.0 "Excellent"
(3 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Aircondition
Details
WeNeedaVacation
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House Aircondition Oak Bluffs
Sep 18 - Sep 25
$500 per night
House ∙ 6 guests ∙ 3 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
Aircondition
Details
WeNeedaVacation
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Vacation rentals with Wi-Fi

House Internet Oak Bluffs
May 1 - May 8
-22%
$422
$329 per night
House ∙ 7 guests ∙ 2 bedrooms
4.9/5.0 "Excellent"
(7 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Internet
Details
WeNeedaVacation
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House Internet Oak Bluffs
Sep 4 - Sep 11
$572 per night
House ∙ 6 guests ∙ 2 bedrooms
5.0/5.0 "Excellent"
(3 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Internet
Details
WeNeedaVacation
View deal
House Internet Oak Bluffs
Sep 11 - Sep 18
-40%
$2,143
$1,286 per night
House ∙ 10 guests ∙ 7 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
Internet
Details
WeNeedaVacation
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Vacation homes and cottages with a garden

House Yard Oak Bluffs
Oct 23 - Oct 30
$1,085 per night
House ∙ 10 guests ∙ 4 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
Yard
Details
NextTrip
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House Yard Oak Bluffs
Oct 23 - Oct 30
-45%
$1,135
$624 per night
House ∙ 6 guests ∙ 3 bedrooms
Oak Bluffs, Dukes County, Massachusetts, United States
Yard
Details
NextTrip
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Popular Rental Amenities in Oak Bluffs

  • No smoking (282)
  • Internet (278)
  • TV (261)
  • Air conditioning (239)
  • Microwave (224)
  • Kitchen (223)
  • Washer (201)
  • Grill (189)
  • Dishwasher (159)
  • Wheelchair access (79)
  • Fireplace (60)
  • Pet allowed (54)

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 "internet" and "TVs" are the most frequently offered amenities in Oak Bluffs. Plan your vacation in advance if you want a rental providing a crib or you enjoy soaking in the hot tub. There are just 15 listed properties providing "cribs" and 16 properties providing "Jacuzzis."

The Weather in Oak Bluffs

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41°
27°
16 days 16
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39°
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15 days 15
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28°
15 days 15
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37°
12 days 12
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48°
13 days 13
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73°
55°
11 days 11
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81°
64°
11 days 11
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79°
61°
9 days 9
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75°
54°
9 days 9
max.
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64°
46°
13 days 13
max.
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54°
37°
10 days 10
max.
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48°
34°
16 days 16
Jan.
Feb.
Mar.
Apr.
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 January while the driest month is August.

Accommodations for your vacation in Oak Bluffs

Many of the accommodations (65.22%) 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 1,550 ft² and they cost, on average, $702 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 hotel rooms, which are the second most popular type of accommodation in Oak Bluffs. Our data shows that the median price of hotel rooms is $451 a night for an area of 330 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 312 properties
Where to find the best food in Oak Bluffs?

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.

What are the best activities for families in Oak Bluffs?

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.

Where are the unique attractions in Oak Bluffs?

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.

How much does it cost to rent a vacation rental in Oak Bluffs?

The average nightly price for vacation rentals in Oak Bluffs is $129.

What amenities are most popular for vacation homes in Oak Bluffs?

Most travelers search for internet, TVs, and barbecues when booking a vacation rental in Oak Bluffs.

How many vacation rentals are in Oak Bluffs?

Discover 317 vacation rentals available to book in Oak Bluffs.

Are pets allowed in vacation rentals in Oak Bluffs?

Yes, there are 67 vacation homes in Oak Bluffs that allow pets, with an average price of $481 per night.

What's the best time of year to travel to Oak Bluffs?

If booking a vacation rental in Oak Bluffs, consider that rainy season is usually in January or December, with August often being the driest.

We list offers from thousands of providers, including:

Booking.com Vacation Rentals in Oak Bluffs TripAdvisor Vacation Rentals in Oak Bluffs Vrbo Vacation Rentals in Oak Bluffs Airbnb 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 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

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