Airbnbs in Oak Bluffs

Oak Bluffs

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$100 - $199

From $200

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Popular amenities for Airbnbs in Oak Bluffs

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Airbnbs with air conditioning

Pet-Friendly Airbnbs

Airbnbs with internet

Airbnbs with TV

Top-rated airbnbs in Oak Bluffs

Browse our top rated airbnbs offers

Dec 2 - Dec 9

-41%

$299

$176 per night

Airbnb ∙ 4 guests ∙ 1 bedroom

Cottage in Oak Bluffs with Yard & Grill

4.9

Outstanding (132 ratings)

Oak Bluffs, Dukes County, Massachusetts, United States

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Oct 3 - Oct 10

$180 per night

Airbnb ∙ 2 guests ∙ 1 bedroom

Vacation Home in Vineyard Haven with Yard

4.6

Excellent (31 ratings)

Oak Bluffs, Dukes County, Massachusetts, United States

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Dec 23 - Dec 30

$250 per night

Airbnb ∙ 2 guests ∙ 1 bedroom

Apartment in Vineyard Haven with Grill

4.7

Excellent (3 ratings)

Oak Bluffs, Dukes County, Massachusetts, United States

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Best Deals and Discounts on Airbnbs

Save up to 54%

Jan 19 - Jan 26

-54%

$419

$192 per night

Airbnb ∙ 4 guests ∙ 2 bedrooms

Classic Cottage in Edgartown with Grill & Yard

4.9

Outstanding (27 ratings)

Oak Bluffs, Dukes County, Massachusetts, United States

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May 24 - May 31

-53%

$425

$200 per night

Airbnb ∙ 6 guests ∙ 4 bedrooms

Nice Vacation Home in Vineyard Haven with Grill & Yard

5.0

Outstanding (34 ratings)

Oak Bluffs, Dukes County, Massachusetts, United States

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Sep 14 - Sep 21

-44%

$470

$262 per night

Airbnb ∙ 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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Airbnbs in Oak Bluffs: Top Accommodations

Oct 21 - Oct 28

$360 per night

Airbnb ∙ 6 guests ∙ 3 bedrooms

Beachfront Cottage in Vineyard Haven with Grill

4.9

Outstanding (71 ratings)

Oak Bluffs, Dukes County, Massachusetts, United States

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Sep 12 - Sep 19

$850 per night

Airbnb ∙ 12 guests ∙ 5 bedrooms

Wonderful House in Oak Bluffs with Grill + Clear View

4.8

Outstanding (37 ratings)

Oak Bluffs, Dukes County, Massachusetts, United States

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Oct 21 - Oct 28

$215 per night

Airbnb ∙ 6 guests ∙ 4 bedrooms

House in Vineyard Haven with Extra Parking

4.8

Outstanding (47 ratings)

Oak Bluffs, Dukes County, Massachusetts, United States

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Sep 14 - Sep 21

-44%

$470

$262 per night

Airbnb ∙ 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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May 24 - May 31

-51%

$929

$458 per night

Airbnb ∙ 10 guests ∙ 6 bedrooms

House in Vineyard Haven with Grill & Yard

4.8

Outstanding (31 ratings)

Oak Bluffs, Dukes County, Massachusetts, United States

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May 24 - May 31

-57%

$1,171

$500 per night

Airbnb ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Vineyard Haven with Yard & Grill + Ocean Views

4.9

Outstanding (24 ratings)

Oak Bluffs, Dukes County, Massachusetts, United States

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Dec 23 - Dec 30

-58%

$650

$275 per night

Airbnb ∙ 8 guests ∙ 3 bedrooms

Comfortable Vacation Home in Oak Bluffs with Yard & Grill + Exceptional View

4.9

Outstanding (87 ratings)

Oak Bluffs, Dukes County, Massachusetts, United States

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Jun 15 - Jun 22

-44%

$900

$500 per night

Airbnb ∙ 9 guests ∙ 5 bedrooms

Vacation Home in Vineyard Haven with Yard & Grill

4.8

Outstanding (33 ratings)

Oak Bluffs, Dukes County, Massachusetts, United States

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Dec 23 - Dec 30

-43%

$600

$343 per night

Airbnb ∙ 6 guests ∙ 3 bedrooms

Vacation Home in Oak Bluffs with Yard & Grill

4.5

Excellent (29 ratings)

Oak Bluffs, Dukes County, Massachusetts, United States

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Budget-friendly airbnbs in Oak Bluffs

Our top value vacation rentals for airbnbs

May 24 - May 31

$300 per night

Airbnb ∙ 4 guests ∙ 2 bedrooms

Vacation Home in Vineyard Haven with Grill & Yard

4.6

Excellent (28 ratings)

Oak Bluffs, Dukes County, Massachusetts, United States

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Jun 15 - Jun 22

$929 per night

Airbnb ∙ 13 guests ∙ 6 bedrooms

Vacation Home in Vineyard Haven with Yard & Grill

4.8

Outstanding (53 ratings)

Oak Bluffs, Dukes County, Massachusetts, United States

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Oct 21 - Oct 28

-80%

$1,600

$324 per night

Airbnb ∙ 12 guests ∙ 6 bedrooms

Vacation Home in Vineyard Haven with Grill & Yard

4.9

Outstanding (20 ratings)

Oak Bluffs, Dukes County, Massachusetts, United States

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Stay Cool: Airbnbs with Air Conditioning

Mar 30 - Apr 6

-45%

$1,108

$608 per night

Airbnb ∙ 14 guests ∙ 5 bedrooms

Vacation Home in Edgartown with Grill, Pool & Yard

5.0

Outstanding (27 ratings)

Oak Bluffs, Dukes County, Massachusetts, United States

Air conditioning

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Jun 1 - Jun 8

-43%

$1,000

$575 per night

Airbnb ∙ 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

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Nov 18 - Nov 25

-17%

$1,286

$1,072 per night

Airbnb ∙ 20 guests ∙ 11 bedrooms

Vacation Home in Edgartown with Grill, Yard & Pool

4.8

Outstanding (32 ratings)

Oak Bluffs, Dukes County, Massachusetts, United States

Air conditioning

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Airbnbs with Kitchens

Oct 21 - Oct 28

$350 per night

Airbnb ∙ 9 guests ∙ 4 bedrooms

Lovely Vacation Home in Oak Bluffs with Yard & Grill

4.3

Very good (4 ratings)

Oak Bluffs, Dukes County, Massachusetts, United States

Kitchen

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Nov 18 - Nov 25

-30%

$1,000

$700 per night

Airbnb ∙ 8 guests ∙ 4 bedrooms

Nice Vacation Home in Oak Bluffs with Separate Patio

5.0

Outstanding (29 ratings)

Oak Bluffs, Dukes County, Massachusetts, United States

Kitchen

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Oct 21 - Oct 28

$325 per night

Airbnb ∙ 7 guests ∙ 3 bedrooms

House in Vineyard Haven with Grill & Yard

4.7

Excellent (24 ratings)

Oak Bluffs, Dukes County, Massachusetts, United States

Kitchen

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Soak Up the Sun: Airbnbs with Patios

May 3 - May 10

-49%

$822

$422 per night

Airbnb ∙ 6 guests ∙ 2 bedrooms

House in Edgartown with Loft Balcony

4.9

Outstanding (41 ratings)

Oak Bluffs, Dukes County, Massachusetts, United States

Balcony/Patio

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Apr 13 - Apr 20

-55%

$885

$400 per night

Airbnb ∙ 8 guests ∙ 4 bedrooms

Pleasant House in Oak Bluffs with Yard & Grill

5.0

Outstanding (35 ratings)

Oak Bluffs, Dukes County, Massachusetts, United States

Balcony/Patio

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Oct 7 - Oct 14

-28%

$553

$400 per night

Airbnb ∙ 4 guests ∙ 2 bedrooms

Cottage in Oak Bluffs with Grill

4.0

Very good

Oak Bluffs, Dukes County, Massachusetts, United States

Balcony/Patio

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Airbnbs with Hot Tubs

Rentals Featuring Jacuzzis and Whirlpools

Jun 8 - Jun 15

-70%

$2,358

$715 per night

Airbnb ∙ 8 guests ∙ 4 bedrooms

Charming House in Oak Bluffs with Grill, Pool & Jacuzzi

5.0

Outstanding (7 ratings)

Oak Bluffs, Dukes County, Massachusetts, United States

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Oct 21 - Oct 28

-60%

$886

$358 per night

Airbnb ∙ 8 guests ∙ 4 bedrooms

House in Oak Bluffs with Grill, Hot Tub

5.0

Outstanding (1 rating)

Oak Bluffs, Dukes County, Massachusetts, United States

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Oct 14 - Oct 21

-36%

$400

$258 per night

Airbnb ∙ 6 guests ∙ 3 bedrooms

House in Oak Bluffs with Nice Patio + Ocean View

5.0

Outstanding (5 ratings)

Oak Bluffs, Dukes County, Massachusetts, United States

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Airbnbs in Oak Bluffs for Any Type of Traveler

Traveling with a group of eight or more people in Oak Bluffs?

January is the most affordable month to stay in Oak Bluffs with a large group, when nightly prices for Airbnbs will range from $595 to $1,087 per night. Book unique Airbnbs for big groups in Oak Bluffs, complete with private pool, large kitchen, and plenty of space to relax. HomeToGo features many Airbnbs in Oak Bluffs with 8+ bedrooms and eight or more bathrooms. Start searching our top Airbnbs for large groups and plan the perfect getaway!

Want to plan a large family getaway in Oak Bluffs?

You will find lots of Airbnbs in Oak Bluffs have family-friendly amenities, including private pools, game rooms, hot tubs, and many others. Oak Bluffs has tons of fun family-friendly activities to do, including swimming, hiking, biking, and many other outdoor activities. Take a look at HomeToGo's selection of large Airbnbs in Oak Bluffs, perfect for a big family with five or more beds and lots of bathrooms. Start browsing for family-friendly Airbnbs now! Many Airbnbs in Oak Bluffs will cost around $707 per day for a family of 5 people but there are many affordable options in Oak Bluffs to choose from.

Booking a private trip in Oak Bluffs with your loved one?

The cheapest time to book is January with prices starting at $146 per night. You can find tons of exciting things to try with your partner on your private trip, including hiking, swimming, biking, and many other outdoor activities. Book luxurious Airbnbs in Oak Bluffs for a couples getaway, equipped with hot tub, sauna, and a amazing view of Oak Bluffs's stunning scenery. Browse HomeToGo's best offers for romantic retreats in Oak Bluffs today!

Information about Airbnbs in Oak Bluffs

💳 Highest rates	in August
😎 Least busy month	October
🛏️ Popular home types	House rental and Cabin
🌡️ Hottest months	July and August
❄️ Coldest months	February and January
🌧️ Rainiest months	16 rainy days in January and December

Frequently Asked Questions

What types of vacation homes can I find for Airbnbs in Oak Bluffs?

There is a lot of Cabin and House rental that are perfect for Airbnbs in Oak Bluffs.

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

HomeToGo has great rentals for Airbnbs in Oak Bluffs, with prices as low as $146 per night.

Can I find a vacation rental for a group for Airbnbs in Oak Bluffs?

House rental in Oak Bluffs may fit 8 guests.

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