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

Oak Bluffs Vacation Rentals

Find 1,526 available offers from 6 partners
Oak Bluffs
Anytime
Guests

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+
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.

Show all 1,526 properties

Best Vacation Home Deals in Oak Bluffs

Save up to 76%

Cottage Oak Bluffs
Dec 9 - Dec 16
-41%
$299
$176 per night
Cottage ∙ 4 guests ∙ 1 bedroom
Cottage in Oak Bluffs with Yard & Grill
4.9
Outstanding (148 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Details
Vrbo
View deal
View deal
Cottage Oak Bluffs
Jan 19 - Jan 26
-76%
$786
$192 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
Classic Cottage in Edgartown with Grill & Yard
4.9
Outstanding (26 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Details
Vrbo
View deal
View deal
House Oak Bluffs
May 24 - May 31
-53%
$425
$200 per night
House ∙ 6 guests ∙ 4 bedrooms
Nice Vacation Home in Vineyard Haven with Grill & Yard
5.0
Outstanding (37 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Details
Vrbo
View deal
View deal

Find a rental that matches your criteria among the 1,526 welcoming properties from 6 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 54%.

Top-Rated Rentals and Accommodations in Oak Bluffs

Book Vacation Rental Offers with the Highest User Rating

Cottage Oak Bluffs
Jan 19 - Jan 26
$360 per night
Cottage ∙ 6 guests ∙ 3 bedrooms
Beachfront Cottage in Vineyard Haven with Grill
4.8
Outstanding (73 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Details
Vrbo
View deal
View deal
Cottage Oak Bluffs
Apr 6 - Apr 13
$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
Details
Vrbo
View deal
View deal
House Oak Bluffs
Oct 7 - Oct 14
$179 per night
House ∙ 2 guests ∙ 1 bedroom
Vacation Home in Vineyard Haven with Yard
4.6
Excellent (31 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Details
Vrbo
View deal
View deal

Recommended Vacation Rentals in Oak Bluffs

Find your perfect vacation rental in Oak Bluffs: from $145 per night

Apartment Oak Bluffs
Mar 9 - Mar 16
-79%
$695
$145 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Rental Apartment in Oak Bluffs with Grill & Yard
4.9
Outstanding (41 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Details
Vrbo
View deal
View deal
House Oak Bluffs
Sep 21 - Sep 28
-19%
$1,044
$850 per night
House ∙ 12 guests ∙ 5 bedrooms
Wonderful House in Oak Bluffs with Grill + Clear View
4.8
Outstanding (51 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Details
Vrbo
View deal
View deal
House Oak Bluffs
Jan 19 - Jan 26
-43%
$601
$343 per night
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Oak Bluffs with Yard & Grill
4.6
Excellent (44 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Details
Vrbo
View deal
View deal
House Oak Bluffs
Dec 23 - Dec 30
-50%
$551
$275 per night
House ∙ 8 guests ∙ 3 bedrooms
Comfortable Vacation Home in Oak Bluffs with Yard & Grill + Exceptional View
4.9
Outstanding (97 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Details
Vrbo
View deal
View deal
House Oak Bluffs
May 24 - May 31
-51%
$1,021
$500 per night
House ∙ 8 guests ∙ 4 bedrooms
Vacation Home in Vineyard Haven with Yard & Grill + Ocean Views
5.0
Outstanding (42 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Details
Vrbo
View deal
View deal
House Oak Bluffs
May 24 - May 31
-51%
$929
$458 per night
House ∙ 10 guests ∙ 6 bedrooms
House in Vineyard Haven with Grill & Yard
4.9
Outstanding (39 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Details
Vrbo
View deal
View deal
House Oak Bluffs
Oct 21 - Oct 28
-28%
$301
$215 per night
House ∙ 6 guests ∙ 4 bedrooms
House in Vineyard Haven with Extra Parking
4.7
Excellent (55 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Details
Vrbo
View deal
View deal
House Oak Bluffs
Jun 15 - Jun 22
-44%
$901
$500 per night
House ∙ 9 guests ∙ 5 bedrooms
Vacation Home in Vineyard Haven with Yard & Grill
4.8
Outstanding (37 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Details
Vrbo
View deal
View deal
House Oak Bluffs
Oct 14 - Oct 21
-44%
$1,572
$880 per night
House ∙ 10 guests ∙ 5 bedrooms
House in Oak Bluffs with Grill + Water View
5.0
Outstanding (27 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Details
Vrbo
View deal
View deal
See all offers

Budget-friendly Vacation Rentals in Oak Bluffs

Find Fantastic yet Inexpensive Offers

House Oak Bluffs
Jun 1 - Jun 8
-35%
$495
$324 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
Details
Vrbo
View deal
View deal
House Oak Bluffs
Jun 15 - Jun 22
$929 per night
House ∙ 13 guests ∙ 6 bedrooms
Vacation Home in Vineyard Haven with Yard & Grill
4.8
Outstanding (52 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Details
Vrbo
View deal
View deal
House Oak Bluffs
May 24 - May 31
$300 per night
House ∙ 4 guests ∙ 2 bedrooms
Vacation Home in Vineyard Haven with Grill & Yard
4.6
Excellent (31 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Details
Vrbo
View deal
View deal

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
Apr 6 - Apr 13
-45%
$1,108
$608 per night
House ∙ 14 guests ∙ 5 bedrooms
Vacation Home in Edgartown with Grill, Pool & Yard
5.0
Outstanding (41 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Air conditioning
Details
Vrbo
View deal
View deal
House  Oak Bluffs
Jun 1 - Jun 8
-43%
$1,000
$575 per night
House ∙ 10 guests ∙ 5 bedrooms
Private Vacation Home in Falmouth with Grill + Ocean Views + Beach Nearby
5.0
Outstanding (51 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Air conditioning
Details
Vrbo
View deal
View deal
House  Oak Bluffs
Nov 11 - Nov 18
-65%
$1,030
$356 per night
House ∙ 10 guests ∙ 4 bedrooms
Vacation Home in Edgartown with Grill & Yard + Picturesque Views
5.0
Outstanding (5 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Air conditioning
Details
Vrbo
View deal
View deal
See all offers

Apartments and vacation rentals with a kitchen

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

Cottage  Oak Bluffs
May 24 - May 31
-46%
$601
$325 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
Cottage in Vineyard Haven with Warm Fireplace
4.9
Outstanding (27 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Kitchen
Details
Vrbo
View deal
View deal
House  Oak Bluffs
Jun 29 - Jul 6
$325 per night
House ∙ 7 guests ∙ 3 bedrooms
House in Vineyard Haven with Grill & Yard
4.7
Excellent (27 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Kitchen
Details
Vrbo
View deal
View deal
Cottage  Oak Bluffs
Oct 21 - Oct 28
$420 per night
Cottage ∙ 6 guests ∙ 2 bedrooms
Cottage in Vineyard Haven with Grill & Yard
4.3
Very good (28 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Kitchen
Details
Vrbo
View deal
View deal
See all offers

Best vacation rentals with a balcony

Looking for a home with a balcony? Check out these vacation homes in Oak Bluffs with their own private patios and balconies.

House  Oak Bluffs
May 3 - May 10
-53%
$893
$422 per night
House ∙ 6 guests ∙ 2 bedrooms
House in Edgartown with Loft Balcony
4.9
Outstanding (41 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Balcony
Details
Vrbo
View deal
View deal
House  Oak Bluffs
Oct 14 - Oct 21
-55%
$886
$400 per night
House ∙ 8 guests ∙ 4 bedrooms
Pleasant House in Oak Bluffs with Yard & Grill
4.9
Outstanding (49 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Balcony
Details
Vrbo
View deal
View deal
House  Oak Bluffs
May 11 - May 18
$900 per night
House ∙ 12 guests ∙ 5 bedrooms
Vacation Home in Oak Bluffs with Yard & Grill + Ocean Views
4.7
Excellent (39 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Balcony
Details
Vrbo
View deal
View deal
See all offers

Popular Rental Amenities in Oak Bluffs

  • Air conditioning (1,449)
  • Pet-friendly (262)
  • WiFi (1,590)
  • TV (1,518)
  • Kitchen (1,247)
  • Washing machine (1,057)
  • Pool (353)
  • Grill (1,040)
  • Parking (51)
  • Balcony/patio (272)
  • Dishwasher (857)
  • Microwave (1,207)

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'd like to have a fenced-in yard or you want a rental providing a crib. There are just 62 listed properties providing "Fenced" and 58 properties providing "Crib."

Price and Availability Index in Oak Bluffs

Click on any bar to see price and availability information

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 August (8/24 - 8/31) go up to $1,003 per night, which is the highest average price in the next 12 months. Prices are more affordable in February (2/17 - 2/24).

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 February (2/3 - 2/10), with only 23% of the rentals available. The week with the most available rentals is in October (10/21 - 10/28), with 61% 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.
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

Wed, 27 Sep
62°
57°

0%

8 h

6 mi/h

Thu, 28 Sep
62°
57°

10%

9 h

6 mi/h

Fri, 29 Sep
64°
59°

15%

4 h

6 mi/h

Sat, 30 Sep
64°
60°

10%

2 h

11 mi/h

Sun, 1 Oct
69°
60°

0%

11 h

9 mi/h

Mon, 2 Oct
64°
57°

0%

11 h

8 mi/h

Tue, 3 Oct
62°
55°

10%

8 h

6 mi/h

Accommodations for your vacation in Oak Bluffs

More than two-thirds of the accommodations (78.1%) 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 200 m² and they cost, on average, $952 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 $665 a night for an area of 100 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 1,526 homes
💳 Possible discounts up to 54%
🌙 Nightly prices starting at $145
⭐ Popular amenities Air conditioning, Pets allowed and Internet
🐾 Pet friendly homes 219 homes
🏊 Vacation rentals with pools 301 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 $145 per night. If you’re interested in a house rental, the average price is $952 per night. A cabin Oak Bluffs will cost on average $665 per night.

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

Currently there are 1,526 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 301 rentals across 6 providers in Oak Bluffs.

Are dogs allowed in vacation rentals in Oak Bluffs?

Absolutely, currently there are 219 rentals in Oak Bluffs that allow dogs , with an average rate of $956 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.

Get inspired for your vacation in Oak Bluffs

Vacation Destinations Near Oak Bluffs

Show more

Top Vacation Ideas

Explore More Vacation Ideas

Show more
image-tag