Vacation rentals in Oak Bluffs - HomeToGo base64Hash Vacation rentals in Oak Bluffs - HomeToGo

Vacation rentals in Oak Bluffs

Find 2,173 available house rentals from 10 partners
Anytime
Guests
Anytime
Guests

  • 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+

  • Booking Options

    • Instant Booking

  • Services

    • Air conditioning
    • WiFi
    • TV
    • Kitchen
    • Washing machine
    • Pool
    • Parking
    • Balcony/patio
    • Dishwasher
    • Microwave
    • Yard
    • Fireplace
    • Hot tub
    • Crib
    Show more

  • Accommodation type

    • Pet-friendly
    • No smoking
    • No pets
    • Wheelchair access

  • Activities

    • Grill
    • Fishing

Top 15 Recommended vacation rentals in Oak Bluffs

Find your perfect vacation rental in Oak Bluffs from just $182 per night!

Apartment Oak Bluffs
Apartment ∙ 7 guests ∙ 2 bedrooms

Children-friendly rental apartment with barbeque | Pet-friendly

Oak Bluffs, Dukes County, Massachusetts, United States
from $254
per night
Very good
from $254
per night
View deal
House Oak Bluffs
House ∙ 15 guests ∙ 5 bedrooms

House with jacuzzi, BBQ & yard | Nature view

Oak Bluffs, Dukes County, Massachusetts, United States
from $1,080
per night
Outstanding(41 ratings)
from $1,080
per night
View deal
House Oak Bluffs
House ∙ 11 guests ∙ 6 bedrooms

House with terrace, barbeque & yard | Nature view | Good for workation

Oak Bluffs, Dukes County, Massachusetts, United States
from $783
per night
Outstanding(68 ratings)
from $783
per night
View deal
House Oak Bluffs
House ∙ 10 guests ∙ 4 bedrooms

Family-oriented lovely house with patio & grill | Pet-friendly

Oak Bluffs, Dukes County, Massachusetts, United States
from $441
per night
Outstanding(9 ratings)
from $441
per night
View deal
House Oak Bluffs
House ∙ 6 guests ∙ 4 bedrooms

Family-friendly vacation home with barbeque & garden | Nature view | Pets are welcome

Oak Bluffs, Dukes County, Massachusetts, United States
from $374
per night
Excellent(44 ratings)
from $374
per night
View deal
House Oak Bluffs
House ∙ 12 guests ∙ 5 bedrooms

Child-friendly vacation home with terrace, barbecue & yard | Perfect for remote work

Oak Bluffs, Dukes County, Massachusetts, United States
from $1,044
per night
Outstanding(2 ratings)
from $1,044
per night
View deal
House Oak Bluffs
House ∙ 10 guests ∙ 4 bedrooms

Family-oriented house with terrace, BBQ & garden

Oak Bluffs, Dukes County, Massachusetts, United States
from $929
per night
Outstanding(52 ratings)
from $929
per night
View deal
House Oak Bluffs
House ∙ 10 guests ∙ 5 bedrooms

House with barbeque, terrace & yard | City view

Oak Bluffs, Dukes County, Massachusetts, United States
from $990
per night
Outstanding(49 ratings)
from $990
per night
View deal
Cottage Oak Bluffs
Cottage ∙ 6 guests ∙ 3 bedrooms

Children-friendly cottage with barbeque | Close to the beach | Pets are welcome

Oak Bluffs, Dukes County, Massachusetts, United States
from $442
per night
Outstanding(3 ratings)
from $442
per night
View deal
House Oak Bluffs
House ∙ 9 guests ∙ 5 bedrooms

Vacation home with grill & terrace

Oak Bluffs, Dukes County, Massachusetts, United States
from $694
per night
Outstanding(8 ratings)
from $694
per night
View deal
Cottage Oak Bluffs
Cottage ∙ 6 guests ∙ 3 bedrooms

Family-friendly lovely cottage with grill & terrace | Nature view

Oak Bluffs, Dukes County, Massachusetts, United States
from $437
per night
Outstanding(90 ratings)
from $437
per night
View deal
House Oak Bluffs
House ∙ 8 guests ∙ 4 bedrooms

Children-friendly vacation home with terrace, jacuzzi & BBQ | City view | Perfect for remote work

Oak Bluffs, Dukes County, Massachusetts, United States
from $996
per night
Outstanding(8 ratings)
from $996
per night
View deal
House Oak Bluffs
House ∙ 10 guests ∙ 6 bedrooms

House with terrace, garden & BBQ | Nature view

Oak Bluffs, Dukes County, Massachusetts, United States
from $380
per night
Outstanding(48 ratings)
from $380
per night
View deal
House Oak Bluffs
House ∙ 12 guests ∙ 5 bedrooms

Vacation home with hot tub, terrace & garden

Oak Bluffs, Dukes County, Massachusetts, United States
from $853
per night
Outstanding(44 ratings)
from $853
per night
View deal
House Oak Bluffs
House ∙ 10 guests ∙ 5 bedrooms

Vacation home with BBQ, garden & patio | Nature view

Oak Bluffs, Dukes County, Massachusetts, United States
from $1,234
per night
Outstanding(25 ratings)
from $1,234
per night
View deal

Vacation rentals and apartments with air conditioning

House Oak Bluffs
from $831
per night
House ∙ 11 guests ∙ 6 bedrooms

Child-friendly nice house with yard, barbeque & terrace | Dogs allowed

4.4
Very good(20 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Air conditioning
View deal
Apartment Oak Bluffs
from $324
per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Children-friendly charming holiday apartment with barbecue | Suitable for remote work

5.0
Outstanding(39 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Air conditioning
View deal
House Oak Bluffs
from $916
per night
House ∙ 6 guests ∙ 3 bedrooms

Family-friendly house with garden, barbeque & patio | Perfect for remote work

5.0
Outstanding(18 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Air conditioning
View deal
See all offers

Vacation rentals with a balcony

House Oak Bluffs
-12%
$371
from $325
per night
House ∙ 6 guests ∙ 3 bedrooms

Children-friendly house with terrace & BBQ

4.4
Very good(46 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Balcony
View deal
House Oak Bluffs
from $424
per night
House ∙ 7 guests ∙ 3 bedrooms

Family-oriented house with BBQ, garden & terrace

4.5
Excellent(52 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Balcony
View deal
House Oak Bluffs
from $506
per night
House ∙ 9 guests ∙ 5 bedrooms

Family-friendly vacation home with BBQ & garden | Nature view

4.9
Outstanding(34 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Balcony
View deal
See all offers

Vacation Rentals With Fireplaces

House Oak Bluffs
from $454
per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with patio, garden & BBQ

4.4
Very good(67 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Fireplace
View deal
House Oak Bluffs
from $485
per night
House ∙ 10 guests ∙ 5 bedrooms

Vacation home with yard & barbeque | City view

5.0
Outstanding(46 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Fireplace
View deal
House Oak Bluffs
from $725
per night
House ∙ 8 guests ∙ 6 bedrooms

Family-friendly house with garden & BBQ | Nature view | Suitable for remote work

5.0
Outstanding(35 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Fireplace
View deal
See all offers

Best Vacation Home Deals in Oak Bluffs

Save up to 16%

House Oak Bluffs
-8%
$1,084
from $1,002
per night
House ∙ 10 guests ∙ 5 bedrooms

Children-friendly vacation home with patio, garden & BBQ

4.3
Very good(51 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
View deal
House Oak Bluffs
-16%
$424
from $356
per night
House ∙ 7 guests ∙ 3 bedrooms

House with BBQ, terrace & garden

4.5
Excellent(52 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
View deal

Browse the 2,173 accommodations available in Oak Bluffs and discover a wonderful rental for your getaway. HomeToGo, a vacation rental search engine, directly sorts all of these vacation rentals so you can save up to 39%!

Budget-friendly Vacation Rentals in Oak Bluffs

Find Fantastic yet Inexpensive Offers

House Oak Bluffs
from $508
per night
House ∙ 8 guests ∙ 4 bedrooms

Lovely vacation home with barbeque, garden & patio | Dogs allowed

4.6
Excellent(6 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
View deal
House Oak Bluffs
from $934
per night
House ∙ 7 guests ∙ 4 bedrooms

Child-friendly beautiful house with patio, barbecue & garden | City view

5.0
Outstanding(39 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
View deal
Cottage Oak Bluffs
from $583
per night
Cottage ∙ 12 guests ∙ 6 bedrooms

Family-oriented charming cottage with barbecue, terrace & yard | Next to the beach | Perfect for remote work

5.0
Outstanding(2 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
View deal

Top-Rated Rentals and Accommodations in Oak Bluffs

Book Vacation Rental Offers with the Highest User Rating

House Oak Bluffs
from $529
per night
House ∙ 8 guests ∙ 4 bedrooms

Fully equipped house with garden, BBQ & patio

4.6
Excellent(46 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
View deal
House Oak Bluffs
from $1,111
per night
House ∙ 9 guests ∙ 4 bedrooms

Child-friendly big vacation home with patio, grill & garden | Next to the beach | Good for workation

4.9
Outstanding(24 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
View deal
House Oak Bluffs
from $499
per night
House ∙ 7 guests ∙ 3 bedrooms

Fully equipped charming house with terrace & barbecue | Nature view

4.9
Outstanding(16 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
View deal

Why choose HomeToGo?

Securely pay and stay your way

Securely pay and stay your way

Choose local, trusted payment methods, plus trip insurance and add-on services.

Award-winning customer service

Award-winning customer service

Experience seamless, hands-on support for any booking questions or concerns.

Verified reviews

Verified reviews

Trust in the quality and comfort of your stay with verified guest reviews.

Price clarity, no surprises

Price clarity, no surprises

Spend your budget exactly as planned by comparing thousands of providers.

Smart search made simple

Smart search made simple

Transform vacation planning into a joy with advanced, AI-powered search tools.

Find your dream stay

Find your dream stay

Explore 15 million+ rentals, the world’s biggest selection of vacation homes.

Popular Rental Amenities in Oak Bluffs

  • Air conditioning (1,956)
  • Pet-friendly (417)
  • WiFi (2,044)
  • TV (1,940)
  • Kitchen (1,757)
  • Washing machine (1,471)
  • Pool (322)
  • Grill (1,159)
  • Parking (74)
  • Balcony/patio (709)
  • Dishwasher (977)
  • Microwave (1,627)

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.

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 2,173 rentals
💳 Possible discounts up to 39%
🌙 Nightly prices starting at $182
⭐ Popular amenities Air conditioning, Pets allowed and Internet
🐾 Pet friendly homes 368 homes
🏊 Vacation rentals with pools 327 homes
50,433 reviews
Oak Bluffs vacation rentals have an average rating of 4.6/5 on 50,433 reviews left by travelers.

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 $182 per night. $940 is the average nightly price for house rentals in Oak Bluffs. Apartment rentals in Oak Bluffs cost on average $602 per night.

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

Currently there are 2,173 rentals in Oak Bluffs to choose from and rent for your trip.

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

Three most popular amenities for home rentals in Oak Bluffs include accommodations that have: Pets allowed, Air conditioning, and Internet.

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

Discover 327 vacation rentals available in Oak Bluffs.

Are pets allowed in vacation homes in Oak Bluffs?

In case if you are traveling with a pet in Oak Bluffs - 17% of vacation homes are pet-friendly.

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

July and August are 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.

Most Popular Destinations

Show more

Top cities to visit

image-tag