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

Oak Bluffs Vacation Rentals

Find 1,658 available offers from 5 partners
Oak Bluffs
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Oak Bluffs
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Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Accommodation types
House
Apartment
Bed and breakfast
Distance to center
1 km
2 km
5 km
Rating
4.5+
4+

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 1,658 properties

Vacation rentals and apartments with air conditioning

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

House  Oak Bluffs
Feb 8 - Feb 15
-54%
$377
$175 per night
House ∙ 6 guests ∙ 4 bedrooms

House in Vineyard Haven with Patio, Grill & Yard

4.8
Outstanding (40 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Air conditioning
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House  Oak Bluffs
Mar 2 - Mar 9
-39%
$575
$350 per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation Home in Oak Bluffs with Patio & Grill

Oak Bluffs, Dukes County, Massachusetts, United States
Air conditioning
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House  Oak Bluffs
Nov 16 - Nov 23
$200 per night
House ∙ 6 guests ∙ 4 bedrooms

Nice Vacation Home in Vineyard Haven with Patio, Grill & Yard

5.0
Outstanding (37 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Air conditioning
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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  Oak Bluffs
Oct 19 - Oct 26
-27%
$341
$249 per night
House ∙ 4 guests ∙ 2 bedrooms

Vacation Home in Oak Bluffs with Patio, Yard & Grill + Waterfront Views

4.4
Very good (34 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Kitchen
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House  Oak Bluffs
May 3 - May 10
-63%
$663
$244 per night
House ∙ 7 guests ∙ 4 bedrooms

Beautiful Vacation Home in Oak Bluffs with Patio & Yard

3.9
Good (9 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Kitchen
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House  Oak Bluffs
Mar 2 - Mar 9
$405 per night
House ∙ 10 guests ∙ 4 bedrooms

House in Oak Bluffs with Patio & Yard

5.0
Outstanding (14 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Kitchen
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Vacation rentals with Wi-Fi

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

House  Oak Bluffs
Sep 21 - Sep 28
-43%
$1,000
$575 per night
House ∙ 13 guests ∙ 6 bedrooms

Vacation Home in Oak Bluffs with Grill & Patio + Water View

5.0
Outstanding (12 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Internet
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House  Oak Bluffs
Aug 24 - Aug 31
$400 per night
House ∙ 7 guests ∙ 3 bedrooms

Charming House in Vineyard Haven with Patio & Grill

4.9
Outstanding (12 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Internet
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House  Oak Bluffs
Feb 15 - Feb 22
$1,500 per night
House ∙ 15 guests ∙ 5 bedrooms

Entire House in Edgartown with Yard, Grill & Patio

5.0
Outstanding (35 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Internet
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Best Vacation Home Deals in Oak Bluffs

Save up to 57%

House Oak Bluffs
Jun 15 - Jun 22
-35%
$772
$500 per night
House ∙ 9 guests ∙ 5 bedrooms

Vacation Home in Vineyard Haven with Yard, Patio & Grill

4.8
Outstanding (37 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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House Oak Bluffs
Jun 2 - Jun 9
-57%
$482
$205 per night
House ∙ 6 guests ∙ 3 bedrooms

Rental Vacation Home in Vineyard Haven with Yard & Grill

5.0
Outstanding (2 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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Condo Oak Bluffs
Feb 28 - Mar 6
-57%
$883
$380 per night
Condo ∙ 4 guests ∙ 2 bedrooms

Charming Condo in Oak Bluffs + Beach Views + Next to Beach

5.0
Outstanding (29 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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Find a rental that matches your criteria among the 1,658 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 55%.

Recommended Vacation Rentals in Oak Bluffs

Find your perfect vacation rental in Oak Bluffs: from $160 per night

House Oak Bluffs
Mar 2 - Mar 9
$779 per night
House ∙ 12 guests ∙ 3 bedrooms

Vacation Home in Oak Bluffs with Patio & Pool + Peaceful View

Oak Bluffs, Dukes County, Massachusetts, United States
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Cottage Oak Bluffs
Dec 6 - Dec 13
$170 per night
Cottage ∙ 4 guests ∙ 1 bedroom

Cottage in Oak Bluffs with Patio, Yard & Grill

4.9
Outstanding (156 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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House Oak Bluffs
Jun 7 - Jun 14
$900 per night
House ∙ 10 guests ∙ 5 bedrooms

House in Vineyard Haven with Patio, Yard & Grill

5.0
Outstanding (20 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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Cottage Oak Bluffs
Apr 27 - May 4
-46%
$465
$250 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Classic Cottage in Edgartown with Grill, Patio & Yard

4.9
Outstanding (25 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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House Oak Bluffs
Feb 8 - Feb 15
-71%
$858
$250 per night
House ∙ 10 guests ∙ 6 bedrooms

House in Vineyard Haven with Grill, Patio & Yard

4.9
Outstanding (43 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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House Oak Bluffs
Apr 27 - May 4
-18%
$236
$193 per night
House ∙ 5 guests ∙ 2 bedrooms

House in Oak Bluffs with Yard, Grill & Patio

4.8
Outstanding (42 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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House Oak Bluffs
Oct 19 - Oct 26
$350 per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation Home in Vineyard Haven with Yard, Patio & Grill

4.9
Outstanding (25 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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Cottage Oak Bluffs
Apr 27 - May 4
$592 per night
Cottage ∙ 8 guests ∙ 5 bedrooms

Cottage in Oak Bluffs with Private Parking

5.0
Outstanding (32 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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House Oak Bluffs
Dec 6 - Dec 13
$279 per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation Home in Edgartown with Grill & Yard

4.1
Very good (38 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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Budget-friendly Vacation Rentals in Oak Bluffs

Find Fantastic yet Inexpensive Offers

Cottage Oak Bluffs
Sep 21 - Sep 28
-17%
$1,200
$995 per night
Cottage ∙ 8 guests ∙ 4 bedrooms

Cottage in Oak Bluffs with Yard, Patio & Grill + 180-Degree Views

5.0
Outstanding (40 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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House Oak Bluffs
Feb 8 - Feb 15
-49%
$385
$195 per night
House ∙ 4 guests ∙ 2 bedrooms

Vacation Home in Edgartown with Grill, Patio & Yard

4.9
Outstanding (83 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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House Oak Bluffs
Nov 16 - Nov 23
$383 per night
House ∙ 10 guests ∙ 5 bedrooms

Vacation Home in West Tisbury with Patio, Yard & Grill

5.0
Outstanding (92 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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Top-Rated Rentals and Accommodations in Oak Bluffs

Book Vacation Rental Offers with the Highest User Rating

House Oak Bluffs
Apr 6 - Apr 13
$716 per night
House ∙ 12 guests ∙ 5 bedrooms

Vacation Home in Oak Bluffs with Patio, Yard & Grill + Ocean Views

4.8
Outstanding (41 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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House Oak Bluffs
Dec 6 - Dec 13
-75%
$1,000
$250 per night
House ∙ 8 guests ∙ 5 bedrooms

Vacation Home in Vineyard Haven with Yard

5.0
Outstanding (32 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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House Oak Bluffs
Mar 30 - Apr 6
-61%
$835
$325 per night
House ∙ 6 guests ∙ 4 bedrooms

Vacation Home in Oak Bluffs with Yard, Patio & Grill

5.0
Outstanding (103 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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Popular Rental Amenities in Oak Bluffs

  • Air conditioning (1,581)
  • Pet-friendly (270)
  • WiFi (1,718)
  • TV (1,641)
  • Kitchen (1,350)
  • Washing machine (1,164)
  • Pool (364)
  • Grill (1,084)
  • Parking (51)
  • Balcony/patio (803)
  • Dishwasher (919)
  • Microwave (1,270)

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 "Air conditioning" and "Pets allowed" are the most frequently offered amenities in Oak Bluffs. Plan your vacation in advance if you need a fenced-in backyard or you want a rental providing a crib. There are just 58 listed properties providing "Fenced" and 117 properties providing "Crib."

The Weather in Oak Bluffs

max.
Min.
41°
27°
16 days 16
max.
Min.
39°
25°
15 days 15
max.
Min.
46°
28°
15 days 15
max.
Min.
55°
37°
12 days 12
max.
Min.
66°
48°
13 days 13
max.
Min.
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, 24 Feb
35°
32°

0%

6 h

11 mi/h

Sun, 25 Feb
30°
28°

0%

6 h

5 mi/h

Mon, 26 Feb
42°
39°

10%

2 h

11 mi/h

Tue, 27 Feb
46°
46°

15%

0 h

12 mi/h

Wed, 28 Feb
50°
50°

15%

0 h

27 mi/h

Thu, 29 Feb
35°
35°

10%

5 h

18 mi/h

Fri, 1 Mar
37°
35°

10%

6 h

10 mi/h

Accommodations for your vacation in Oak Bluffs

More than two-thirds of the accommodations (79.65%) 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 209 m² and they cost, on average, $947 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 cabin, which are the second most popular type of accommodation in Oak Bluffs. Our data shows that the median price of cabin is $666 a night for an area of 96 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 available 1,658 rentals
💳 Possible discounts up to 55%
🌙 Nightly prices starting at $160
⭐ Popular amenities Air conditioning, Pets allowed and Internet
🐾 Pet friendly homes 237 homes
🏊 Vacation rentals with pools 312 homes

Frequently Asked Questions

What is the price per night for a vacation rental in Oak Bluffs?

The average accommodation in Oak Bluffs is priced at $160 per night. If you’re interested in a house rental, the average price is $947 per night. A cabin Oak Bluffs will cost on average $666 per night.

How many vacation rentals are available to book in Oak Bluffs?

Currently there are 1,658 vacation homes available for booking for your upcoming vacation.

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

Travelers look for Air conditioning, Pets allowed, and Internet when booking a vacation rental in Oak Bluffs.

How many vacation homes with pools are in Oak Bluffs?

There are 312 rentals across 5 providers in Oak Bluffs.

Are dogs allowed in vacation rentals in Oak Bluffs?

Absolutely, currently there are 237 rentals in Oak Bluffs that allow dogs , with an average rate of $831 per night.

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. February and January in Oak Bluffs are the coldest, with 25 °F on average.

Find the perfect Oak Bluffs home to match your style

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