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Oak Bluffs Vacation Rentals

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Oak Bluffs
Anytime
Guests

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Price per night
Up to $100
$100 - $199
From $200
Accommodation types
Cabin
House
Apartment
Distance to center
1 km
2 km
5 km
Rating
4.5+
4+
3.5+

Best Vacation Home Deals in Oak Bluffs

Save up to 50%

House Oak Bluffs
Jan 6 - Jan 13
-50%
$1,241
$621 per night
House ∙ 9 guests ∙ 4 bedrooms
Pleasant Vacation Home in Woods Hole with Yard & Grill + Beautiful Views
5.0
"Excellent" (69 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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1,506 welcoming properties from 6 different partner websites, such as stayz or Booking.com, can be compared in Oak Bluffs. By directly analyzing these properties, HomeToGo features the best deals as well as the highest rated vacation homes in Oak Bluffs.

Top-Rated Offers and Accommodations in Oak Bluffs

Book Vacation Rentals with the Highest User Rating

Cottage Oak Bluffs
$490 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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Cottage Oak Bluffs
$800 per night
Cottage ∙ 8 guests ∙ 5 bedrooms
Cottage in Oak Bluffs with Private Parking
5.0
"Excellent" (28 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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House Oak Bluffs
$614 per night
House ∙ 6 guests ∙ 2 bedrooms
Entire House in Vineyard Haven with Warm Fireplace
5.0
"Excellent" (8 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 $233 per night

House Oak Bluffs
Jan 6 - Jan 13
$1,087 per night
House ∙ 14 guests ∙ 5 bedrooms
Vacation Home in Edgartown with Grill, Pool & Yard
5.0
"Excellent" (25 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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House Oak Bluffs
Jan 20 - Jan 27
-56%
$1,291
$566 per night
House ∙ 9 guests ∙ 4 bedrooms
Pleasant Vacation Home in Woods Hole with Yard & Grill + Beautiful Views
5.0
"Excellent" (69 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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Condo Oak Bluffs
$497 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Condo in Oak Bluffs with Grill + Next to Beach
5.0
"Excellent" (70 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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House Oak Bluffs
$739 per night
House ∙ 9 guests ∙ 3 bedrooms
Charming House in Tisbury with Grill & Yard + Ocean View
4.6
"Outstanding" (26 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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House Oak Bluffs
$857 per night
House ∙ 8 guests ∙ 4 bedrooms
Vacation Home in Vineyard Haven with Yard & Grill + Ocean Views
4.9
"Excellent" (22 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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House Oak Bluffs
$391 per night
House ∙ 4 guests ∙ 1 bedroom
House in Vineyard Haven with Grill & Yard
4.9
"Excellent" (41 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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House Oak Bluffs
$379 per night
House ∙ 6 guests ∙ 2 bedrooms
House in Edgartown with Loft Balcony
4.9
"Excellent" (35 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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House Oak Bluffs
$232 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Vineyard Haven with Yard & Grill
5.0
"Excellent" (69 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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House Oak Bluffs
$330 per night
House ∙ 6 guests ∙ 3 bedrooms
Rental Vacation Home in Vineyard Haven with Yard & Grill
5.0
"Excellent" (2 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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Budget-friendly Rentals in Oak Bluffs

Find Fantastic yet Inexpensive Rentals

House Oak Bluffs
$604 per night
House ∙ 10 guests ∙ 5 bedrooms
Family Friendly House in Vineyard Haven with Grill
4.5
"Outstanding" (2 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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House Oak Bluffs
$407 per night
House ∙ 4 guests ∙ 2 bedrooms
House in Edgartown with Grill
5.0
"Excellent" (82 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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Condo Oak Bluffs
$672 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Condo in Oak Bluffs with Grill + Water Views + Next to Beach
4.9
"Excellent" (53 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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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.

Cottage Kitchen Oak Bluffs
$270 per night
Cottage ∙ 4 guests ∙ 1 bedroom
Cottage in Edgartown with Grill & Yard
4.9
"Excellent" (43 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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House Kitchen Oak Bluffs
$407 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
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Cottage Kitchen Oak Bluffs
$245 per night
Cottage ∙ 4 guests ∙ 1 bedroom
Cottage in Oak Bluffs with Yard & Grill
4.8
"Excellent" (128 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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Vacation rentals with Wi-Fi

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

House Internet Oak Bluffs
$306 per night
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Vineyard Haven with Grill
5.0
"Excellent" (3 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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Cottage Internet Oak Bluffs
$745 per night
Cottage ∙ 6 guests ∙ 3 bedrooms
Beautiful Cottage in Vineyard Haven with Yard & Grill
4.8
"Excellent" (34 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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House Internet Oak Bluffs
$362 per night
House ∙ 6 guests ∙ 4 bedrooms
House in Vineyard Haven with Extra Parking
4.8
"Excellent" (44 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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Apartments with a balcony or patio

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

Cottage Balcony/Patio Oak Bluffs
$251 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
Beautiful Cottage in Edgartown with Grill
4.5
"Outstanding" (18 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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House Balcony/Patio Oak Bluffs
$513 per night
House ∙ 5 guests ∙ 3 bedrooms
House in Vineyard Haven with Grill & Yard
5.0
"Excellent" (48 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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Cottage Balcony/Patio Oak Bluffs
$462 per night
Cottage ∙ 4 guests ∙ 1 bedroom
Sunny Cottage in Edgartown with Grill & Yard + Water View
4.8
"Excellent" (55 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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Popular Rental Amenities in Oak Bluffs

  • Air conditioning (1,341)
  • Pool (302)
  • WiFi (1,474)
  • Kitchen (1,130)
  • Pet-friendly (217)
  • TV (1,400)
  • Washing machine (953)
  • Parking (50)
  • Balcony/patio (272)
  • Grill (947)
  • Dishwasher (836)
  • Microwave (1,089)

Filters are conveniently available so you can tailor your search and find the ideal accommodation in Oak Bluffs. You can easily find a rental matching your expectations in Oak Bluffs if you need internet access during your vacation or you want a rental with a pool, as most accommodations provide "Air conditioning" and "Pool." It is also possible to look for a vacation rental in Oak Bluffs if you want a rental providing a crib as 20 of the properties there include "Wheelchair accessible."

Price and Availability Index in Oak Bluffs

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Vacation Rental Price Information in Oak Bluffs

Rental availability information in Oak Bluffs

The Weather in Oak Bluffs

max.
Min.

-3°
16 days 16
max.
Min.

-4°
15 days 15
max.
Min.

-2°
15 days 15
max.
Min.
13°
12 days 12
max.
Min.
19°
13 days 13
max.
Min.
23°
13°
11 days 11
max.
Min.
27°
18°
11 days 11
max.
Min.
26°
16°
9 days 9
max.
Min.
24°
12°
9 days 9
max.
Min.
18°
13 days 13
max.
Min.
12°
10 days 10
max.
Min.

16 days 16
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

The above is a climate diagram for Oak Bluffs. In July maximum temperatures go higher than 27°. On the other hand, you could have temperatures dropping under -4° in February. January is the wettest month.

7-Day Weather Forecast in Oak Bluffs

Wed., 27 Sep.
17°
14°

0%

8 h

10 km/h

Thu., 28 Sep.
17°
14°

10%

9 h

10 km/h

Fri., 29 Sep.
18°
15°

15%

4 h

10 km/h

Sat., 30 Sep.
18°
16°

10%

2 h

19 km/h

Sun., 1 Oct.
21°
16°

0%

11 h

14 km/h

Mon., 2 Oct.
18°
14°

0%

11 h

13 km/h

Tue., 3 Oct.
17°
13°

10%

8 h

10 km/h

Information about vacation rentals in Oak Bluffs

🏡 Vacation rentals available 1,506 homes
💳 Possible discounts up to 50%
🌙 Nightly prices starting at $232
⭐ Popular amenities Air conditioning, Pool and Internet
🐾 Pet friendly homes 216 homes
🏊 Vacation rentals with pools 301 homes

Frequently Asked Questions

What is the typical price of a vacation home in Oak Bluffs?

The nightly price for accommodation in Oak Bluffs starts at $232.

What is the typical availability of House rental in Oak Bluffs?

September has the highest availability of House rental in Oak Bluffs, so you can expect plenty of selection, even for last-minute bookings.

What are the most popular vacation home amenities in Oak Bluffs?

Many travellers are searching for Air conditioning, Pool, and Internet when booking a vacation home in Oak Bluffs.

How many House rental and Cottage can I find in Oak Bluffs?

Oak Bluffs has 1,506 House rental and Cottage available to book.

Are there pet-friendly vacation rentals in Oak Bluffs?

Yes, there are 216 pet-friendly vacation rentals in Oak Bluffs, with an average nightly price of $1,297.

What's the best month to visit Oak Bluffs?

The warmest time of year in Oak Bluffs is July and August, with the nightly price of a vacation home starting at $232.

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