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Oak Bluffs Vacation Rentals

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Price per night
Up to $100
$100 - $199
From $200
Accommodation types
House
Apartment
Bed & Breakfast
Distance to center
Max. 1 km
Max. 2 km
Max. 5 km
Rating
Outstanding: 4.5+
Very Good: 4+
Good: 3.5+

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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Save up to 62%

Best Vacation Home Deals in Oak Bluffs

Cottage Oak Bluffs
Dec 2 - Dec 9
-62%
$465
$179 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
Classic Cottage in Edgartown with Grill & Yard
4.9
"Excellent" (24 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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House Oak Bluffs
May 5 - May 12
-16%
$650
$548 per night
House ∙ 8 guests ∙ 4 bedrooms
Vacation Home in Vineyard Haven with Yard & Grill + Ocean Views
4.9
"Excellent" (18 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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House Oak Bluffs
Jun 4 - Jun 11
-44%
$900
$500 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Oak Bluffs with Grill & Yard
4.9
"Excellent" (22 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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Find a rental that matches your criteria among the 574 welcoming properties from 5 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 44%.

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Top-Rated Rentals and Accommodations in Oak Bluffs

House Oak Bluffs
Dec 9 - Dec 16
-47%
$375
$199 per night
House ∙ 4 guests ∙ 2 bedrooms
House in Edgartown with Grill
5.0
"Excellent" (83 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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House Oak Bluffs
Mar 26 - Apr 2
-21%
$300
$236 per night
House ∙ 2 guests ∙ 1 bedroom
Vacation Home in Vineyard Haven
5.0
"Excellent" (31 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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House Oak Bluffs
Dec 23 - Dec 30
-71%
$1,715
$498 per night
House ∙ 8 guests ∙ 3 bedrooms
House in Edgartown with Pool, Yard & Grill
5.0
"Excellent" (2 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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Recommended Vacation Rentals in Oak Bluffs

Find your perfect vacation rental in Oak Bluffs: from $101 per night

Cottage Oak Bluffs
Dec 2 - Dec 9
-62%
$362
$178 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
Classic Cottage in Edgartown with Grill & Yard
4.9
"Excellent" (24 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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House Oak Bluffs
Nov 17 - Nov 24
$257 per night
House ∙ 8 guests ∙ 4 bedrooms
Vacation Home in Vineyard Haven with Grill & Yard
5.0
"Excellent" (31 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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House Oak Bluffs
May 5 - May 12
-16%
$650
$550 per night
House ∙ 8 guests ∙ 4 bedrooms
Vacation Home in Vineyard Haven with Yard & Grill + Ocean Views
4.9
"Excellent" (18 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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House Oak Bluffs
Apr 15 - Apr 22
$483 per night
House ∙ 10 guests ∙ 4 bedrooms
House in Edgartown with Grill & Yard
5.0
"Excellent" (59 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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House Oak Bluffs
Jan 19 - Jan 26
-25%
$691
$522 per night
House ∙ 8 guests ∙ 3 bedrooms
House in West Tisbury with Yard & Grill
5.0
"Excellent" (62 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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House Oak Bluffs
Oct 21 - Oct 28
-30%
$297
$208 per night
House ∙ 8 guests ∙ 3 bedrooms
Lovely House in Edgartown with Grill & Yard
4.7
"Outstanding" (61 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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Cottage Oak Bluffs
Apr 7 - Apr 14
-17%
$360
$304 per night
Cottage ∙ 6 guests ∙ 3 bedrooms
Beachfront Cottage in Vineyard Haven with Grill
4.8
"Excellent" (71 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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House Oak Bluffs
Jun 23 - Jun 30
-22%
$680
$528 per night
House ∙ 7 guests ∙ 3 bedrooms
Vacation Home in Oak Bluffs
Oak Bluffs, Dukes County, Massachusetts, United States
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House Oak Bluffs
Jun 3 - Jun 10
-64%
$1,000
$356 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Vineyard Haven with Yard & Grill + Frame Views
5.0
"Excellent" (37 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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Find Fantastic yet Inexpensive Offers

Budget-friendly Vacation Rentals in Oak Bluffs

House Oak Bluffs
Oct 21 - Oct 28
$275 per night
House ∙ 8 guests ∙ 3 bedrooms
Comfortable Vacation Home in Oak Bluffs with Yard & Grill + Exceptional View
4.9
"Excellent" (86 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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Condo Oak Bluffs
Oct 20 - Oct 27
-42%
$600
$350 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Condo in Oak Bluffs with Grill + Next to Beach
5.0
"Excellent" (69 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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Condo Oak Bluffs
Mar 26 - Apr 2
-45%
$600
$332 per night
Condo ∙ 5 guests ∙ 2 bedrooms
Condo in Oak Bluffs with Grill + Water Views + Next to Beach
5.0
"Excellent" (51 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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Vacation rentals and apartments with air conditioning

Keep cool during your trip to Oak Bluffs and book a vacation rental with air conditioning.

House Air conditioning Oak Bluffs
Oct 21 - Oct 28
$275 per night
House ∙ 8 guests ∙ 3 bedrooms
Comfortable Vacation Home in Oak Bluffs with Yard & Grill + Exceptional View
4.9
"Excellent" (85 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Air conditioning
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House Air conditioning Oak Bluffs
Mar 25 - Apr 1
-25%
$299
$225 per night
House ∙ 2 guests ∙ 1 bedroom
Vacation Home in Vineyard Haven
5.0
"Excellent" (31 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Air conditioning
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Condo Air conditioning Oak Bluffs
Mar 25 - Apr 1
-49%
$600
$308 per night
Condo ∙ 5 guests ∙ 2 bedrooms
Condo in Oak Bluffs with Grill + Water Views + Next to Beach
5.0
"Excellent" (51 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Air conditioning
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Vacation rentals with Wi-Fi

Stay connected while traveling and book a Oak Bluffs accommodation with high-speed internet.

Condo Internet Oak Bluffs
Oct 20 - Oct 27
-42%
$600
$350 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Condo in Oak Bluffs with Grill + Next to Beach
5.0
"Excellent" (69 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Internet
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House Internet Oak Bluffs
Dec 9 - Dec 16
-47%
$375
$199 per night
House ∙ 4 guests ∙ 2 bedrooms
House in Edgartown with Grill
5.0
"Excellent" (83 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Internet
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House Internet Oak Bluffs
Apr 8 - Apr 15
-23%
$847
$650 per night
House ∙ 10 guests ∙ 4 bedrooms
House in Vineyard Haven with Original Fireplace
5.0
"Excellent" (53 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Internet
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Apartments and vacation rentals with a kitchen

Cook up a feast on your next vacation and book a Oak Bluffs rental with full kitchen.

House Kitchen Oak Bluffs
Mar 16 - Mar 23
-70%
$714
$215 per night
House ∙ 8 guests ∙ 4 bedrooms
Pleasant House in Oak Bluffs with Yard, Grill & Pool
5.0
"Excellent" (34 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Kitchen
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House Kitchen Oak Bluffs
Dec 23 - Dec 30
-39%
$599
$368 per night
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Tisbury with Large Parking + Spectacular Views
5.0
"Excellent" (84 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Kitchen
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House Kitchen Oak Bluffs
Jun 4 - Jun 11
-44%
$900
$500 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Oak Bluffs with Grill & Yard
4.9
"Excellent" (22 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Kitchen
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Popular Rental Amenities in Oak Bluffs

  • Internet (1,747)
  • TV (1,716)
  • Air conditioning (1,557)
  • No smoking (1,510)
  • Kitchen (1,478)
  • Microwave (1,418)
  • Grill (1,248)
  • No pets (1,241)
  • Washer (1,233)
  • Dishwasher (1,011)
  • Yard (822)
  • Fireplace (564)

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 "TV" are the most frequently offered amenities in Oak Bluffs. Plan your vacation in advance if you want a rental with a jacuzzi or you want a rental with a jacuzzi. There are just 40 listed properties providing "Detached" and 39 properties providing "Hot tub."

Price and Availability Index in Oak Bluffs

Vacation Rental Price Information in Oak Bluffs

The graph shows average prices of rentals in Oak Bluffs for the next twelve months. Prices in a week of July (7/8 - 7/15) go up to $947 per night, which is the highest average price in the next 12 months. Prices are more affordable in January (1/14 - 1/21).

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 December (12/30 - 1/6), with only 17% of the rentals available. The week with the most available rentals is in September (9/2 - 9/9), with 62% of the vacation rentals available.

The Weather in Oak Bluffs

max.
Min.
41°
27°
16 days 16
max.
Min.
39°
25°
15 days 15
max.
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46°
28°
15 days 15
max.
Min.
55°
37°
12 days 12
max.
Min.
66°
48°
13 days 13
max.
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73°
55°
11 days 11
max.
Min.
81°
64°
11 days 11
max.
Min.
79°
61°
9 days 9
max.
Min.
75°
54°
9 days 9
max.
Min.
64°
46°
13 days 13
max.
Min.
54°
37°
10 days 10
max.
Min.
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 25° The rainiest month is January while the driest month is August.

7-Day Weather Forecast in Oak Bluffs

Sat, 25 Mar
42°
37°

15%

0 h

15 mi/h

Sun, 26 Mar
50°
44°

15%

5 h

11 mi/h

Mon, 27 Mar
44°
41°

15%

1 h

2 mi/h

Tue, 28 Mar
46°
39°

10%

3 h

6 mi/h

Wed, 29 Mar
44°
37°

5%

10 h

8 mi/h

Thu, 30 Mar
46°
42°

15%

2 h

13 mi/h

Fri, 31 Mar
51°
48°

15%

0 h

21 mi/h

Accommodations for your vacation in Oak Bluffs

Two-thirds of the accommodations (74.68%) in Oak Bluffs are house rental. They are the most typical properties in this destination. In addition, the median size of house rental in Oak Bluffs is 190 m² and they cost, on average, $1,000 a night. Furthermore, if you are going in a group of 8, house rental 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 rental, which are the second most popular type of accommodation in Oak Bluffs. Our data shows that the median price of apartment rental is $476 a night for an area of 92 m².
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.

Information about vacation rentals in Oak Bluffs

🏡 Vacation rentals 574 properties
💳 Possible discounts up to 75%
🌙 Nightly prices starting at $101
⭐ Popular amenities Internet, TV and Air conditioning
🐾 Pet friendly accommodations 345 properties
🏊 Vacation rentals with pools 489 properties

Frequently Asked Questions

What is the average nightly price for a vacation home in Oak Bluffs?

The nightly price of accommodations in Oak Bluffs starts at $101. If you’re interested in a house rental, the average price is $1,000 per night. A apartment rental Oak Bluffs will cost on average $476 per night.

How many vacation rentals are available for booking in Oak Bluffs?

There are 574 vacation homes available for booking for your vacation.

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

Most travelers look for TV, Internet, and Air conditioning when booking a vacation rental in Oak Bluffs.

How many vacation rentals with pools are there in Oak Bluffs?

Discover 489 vacation rentals available in Oak Bluffs for renting.

Are dogs allowed in vacation homes in Oak Bluffs?

Finding a vacation rental in Oak Bluffs that allows pets is easy, with 345 pet-friendly available.

What's the best month to travel to Oak Bluffs?

July and August are typically the warmest months in Oak Bluffs with temperatures around 81 °F. The coldest months in Oak Bluffs are February and January, with 25 °F on average.

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 VacationRentals.com Vacation Rentals in Oak Bluffs HouseTrip Vacation Rentals in Oak Bluffs FlipKey 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 Novasol Vacation Rentals in Oak Bluffs HomeEscape Vacation Rentals in Oak Bluffs

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