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

Vacation rentals in Oak Bluffs

Browse 1,446 available vacation homes and compared across 8 trusted 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 mi
    • 2 mi
    • 3 mi

  • Rating

    • 4.5+
    • 4+

  • 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 most Recommended Vacation Rentals in Oak Bluffs

Discover your ideal Oak Bluffs vacation rental with real-time comparisons of 1,446 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Oak Bluffs
House ∙ 14 guests ∙ 7 bedrooms

Fully equipped wonderful vacation home with patio & BBQ | City view | Close to the beach | Perfect for remote work

Oak Bluffs, Dukes County, Massachusetts, United States
This Oak Bluffs house rental accommodates 14 guests and features a kitchen, balcony, and parking for a perfect getaway.
from $1,984
per night
Outstanding(44 ratings)
from $1,984
per night
View deal
Cabin Oak Bluffs
Cabin ∙ 8 guests ∙ 3 bedrooms

Cottage with patio, garden & barbecue | Nature view

Oak Bluffs, Dukes County, Massachusetts, United States
This Edgartown cabin accommodates up to 8 guests, featuring a kitchen, yard, and parking, perfect for a family getaway.
from $581
per night
Excellent(51 ratings)
from $581
per night
View deal
House Oak Bluffs
House ∙ 9 guests ∙ 4 bedrooms

Vacation home with yard, barbeque & terrace | Nature view

Oak Bluffs, Dukes County, Massachusetts, United States
This Edgartown house rental features a kitchen, yard, and parking, perfectly accommodating up to nine guests for a memorable stay.
from $796
per night
Outstanding(62 ratings)
from $796
per night
View deal
House Oak Bluffs
House ∙ 8 guests ∙ 3 bedrooms

Vacation home with yard, patio & BBQ | Good for workation

Oak Bluffs, Dukes County, Massachusetts, United States
This Oak Bluffs house rental features a fireplace, kitchen, yard, and parking, accommodating up to 8 guests for a perfect getaway.
from $992
per night
Outstanding(27 ratings)
from $992
per night
View deal
House Oak Bluffs
House ∙ 8 guests ∙ 5 bedrooms

Family-friendly charming vacation home with BBQ, garden & patio | City view | Good for workation

Oak Bluffs, Dukes County, Massachusetts, United States
This Edgartown house rental offers a kitchen, yard, parking, and space for 8, perfect for your family getaway.
from $675
per night
Outstanding(33 ratings)
from $675
per night
View deal
Cabin Oak Bluffs
Cabin ∙ 6 guests ∙ 3 bedrooms

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

Oak Bluffs, Dukes County, Massachusetts, United States
This waterfront cabin in Vineyard Haven offers beach access, a kitchen, and parking, perfect for families of six.
from $392
per night
Outstanding(93 ratings)
from $392
per night
View deal
House Oak Bluffs
House ∙ 10 guests ∙ 6 bedrooms

Family-friendly vacation home with barbecue & garden | Dogs allowed

Oak Bluffs, Dukes County, Massachusetts, United States
This Oak Bluffs house rental offers a spacious yard, a cozy fireplace, and room for the whole family, including pets.
from $1,769
per night
Outstanding(8 ratings)
from $1,769
per night
View deal
House Oak Bluffs
House ∙ 10 guests ∙ 3 bedrooms

House | Pets allowed

Oak Bluffs, Dukes County, Massachusetts, United States
This Edgartown house rental accommodates 10, features a fireplace, and welcomes pets for a memorable getaway.
from $630
per night
from $630
per night
View deal
House Oak Bluffs
House ∙ 14 guests ∙ 6 bedrooms

Family-friendly house with terrace, BBQ & yard | City view

Oak Bluffs, Dukes County, Massachusetts, United States
This Vineyard Haven house rental offers a fireplace, kitchen, yard, and balcony, perfect for family gatherings of 14.
from $824
per night
Outstanding(58 ratings)
from $824
per night
View deal
House Oak Bluffs
House ∙ 5 guests ∙ 4 bedrooms

Family-oriented big house with BBQ, terrace & yard | Nature view | Good for workation

Oak Bluffs, Dukes County, Massachusetts, United States
This house rental in Vineyard Haven offers a fireplace, kitchen, yard, and parking, perfect for a family getaway.
from $814
per night
Very good(21 ratings)
from $814
per night
View deal
House Oak Bluffs
House ∙ 8 guests ∙ 4 bedrooms

Family-oriented beautiful house with terrace, barbecue & yard | Close to the beach | Perfect for remote work | Pets allowed

Oak Bluffs, Dukes County, Massachusetts, United States
This waterfront house in Oak Bluffs features a yard, kitchen, and fireplace, making it perfect for families and pets.
from $409
per night
Outstanding(54 ratings)
from $409
per night
View deal
House Oak Bluffs
House ∙ 8 guests ∙ 3 bedrooms

Vacation home with BBQ, yard & terrace | City view

Oak Bluffs, Dukes County, Massachusetts, United States
This house rental in Vineyard Haven features a kitchen, yard, and parking, accommodating up to 8 guests for a memorable getaway.
from $670
per night
Outstanding(57 ratings)
from $670
per night
View deal
House Oak Bluffs
House ∙ 6 guests ∙ 4 bedrooms

Fully equipped vacation home with barbeque, yard & patio | Good for workation

Oak Bluffs, Dukes County, Massachusetts, United States
This house rental in Oak Bluffs features a kitchen, yard, balcony, and parking, perfect for a memorable getaway with friends or family.
from $464
per night
Outstanding(111 ratings)
from $464
per night
View deal
House Oak Bluffs
House ∙ 8 guests ∙ 3 bedrooms

House with grill, patio & yard | City view

Oak Bluffs, Dukes County, Massachusetts, United States
This family-friendly house rental in Vineyard Haven offers a yard, kitchen, balcony, and space for up to eight guests.
from $360
per night
Outstanding(63 ratings)
from $360
per night
View deal
House Oak Bluffs
House ∙ 8 guests ∙ 4 bedrooms

Children-friendly ample vacation home with BBQ, yard & patio

Oak Bluffs, Dukes County, Massachusetts, United States
This house rental in Oak Bluffs offers beach access, a kitchen, and a yard, perfect for families and groups of up to 8.
from $546
per night
Outstanding(97 ratings)
from $546
per night
View deal

Vacation houses with Balconies or Patios

House Oak Bluffs
from $950
per night
House ∙ 9 guests ∙ 4 bedrooms

Vacation home with yard, terrace & barbeque | City view

5.0
Outstanding(42 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Balcony/Patio
View deal
House Oak Bluffs
from $544
per night
House ∙ 7 guests ∙ 3 bedrooms

Fully equipped charming house with terrace & barbecue | City view

4.9
Outstanding(18 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Balcony/Patio
View deal
House Oak Bluffs
from $735
per night
House ∙ 10 guests ∙ 5 bedrooms

Vacation home with yard, barbecue & patio | Nature view

5.0
Outstanding(110 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Balcony/Patio
View deal
See all offers

Vacation rentals with a balcony

House Oak Bluffs
from $570
per night
House ∙ 10 guests ∙ 6 bedrooms

House with terrace, garden & BBQ | Nature view

5.0
Outstanding(56 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Balcony
View deal
House Oak Bluffs
from $1,064
per night
House ∙ 12 guests ∙ 5 bedrooms

Vacation home with terrace, garden & barbeque

4.9
Outstanding(47 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Balcony
View deal
House Oak Bluffs
from $1,424
per night
House ∙ 8 guests ∙ 3 bedrooms

Children-friendly house with garden, patio & BBQ | Suitable for remote work

5.0
Outstanding(10 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Balcony
View deal
See all offers

Vacation rentals and apartments with air conditioning

House Oak Bluffs
from $1,531
per night
House ∙ 10 guests ∙ 5 bedrooms

House with yard, terrace & grill

5.0
Outstanding(11 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Air conditioning
View deal
House Oak Bluffs
from $689
per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with yard, barbecue & terrace

5.0
Outstanding(41 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Air conditioning
View deal
House Oak Bluffs
from $582
per night
House ∙ 9 guests ∙ 5 bedrooms

Vacation home with garden, barbecue & patio | Nature view

4.8
Outstanding(41 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Air conditioning
View deal
See all offers

Budget-friendly rental options

Enjoy affordable vacation rentals in Oak Bluffs offering exceptional value for money

House Oak Bluffs
from $874
per night
House ∙ 10 guests ∙ 4 bedrooms

Child-friendly pleasant house with patio, barbecue & yard | Nature view | Perfect for remote work | Dogs allowed

4.9
Outstanding(26 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
View deal
House Oak Bluffs
from $652
per night
House ∙ 10 guests ∙ 3 bedrooms

Vacation home with barbecue, jacuzzi & patio | City view

4.9
Outstanding(40 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
View deal
Cabin Oak Bluffs
from $427
per night
Cabin ∙ 3 guests ∙ 2 bedrooms

Cottage with garden, terrace & barbecue | City view

4.9
Outstanding(70 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
View deal

Top-Rated Vacation rentals in Oak Bluffs

Book the highest-rated Oak Bluffs vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

House Oak Bluffs
from $548
per night
House ∙ 6 guests ∙ 2 bedrooms

House with barbecue, garden & patio

5.0
Outstanding(32 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
View deal
Farmhouse Oak Bluffs
from $499
per night
Farmhouse ∙ 8 guests ∙ 4 bedrooms

Farm with grill

5.0
Outstanding(26 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
View deal
House Oak Bluffs
from $1,071
per night
House ∙ 11 guests ∙ 6 bedrooms

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

5.0
Outstanding(71 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
View deal

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Popular Features & Amenities in Oak Bluffs

  • Air conditioning (1,367)
  • Pet-friendly (283)
  • WiFi (1,397)
  • TV (1,387)
  • Kitchen (1,115)
  • Washing machine (1,012)
  • Pool (270)
  • Grill (1,039)
  • Parking (49)
  • Balcony/patio (730)
  • Dishwasher (819)
  • Microwave (1,025)

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 1,446 rentals
💳 Possible discounts up to 16%
🌙 Nightly prices starting at $320
⭐ Popular amenities Air conditioning, Pets allowed and Internet
🐾 Pet friendly homes 260 homes
🏊 Vacation rentals with pools 279 homes

Frequently Asked Questions

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

On average, vacation rentals in Oak Bluffs cost around $320 per night. Average prices for house rentals are $1,286 per night. Cottages in Oak Bluffs cost $872 per night on average.

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

Currently there are 1,446 vacation homes in Oak Bluffs to choose from and rent for your trip.

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

If you're looking to book a vacation rental in Oak Bluffs, the most popular amenities are: Air conditioning, Pets allowed and Internet.

How many vacation rentals with a pool are there in Oak Bluffs?

Oak Bluffs offers 279 Hotel room and Aparthotel options on offer to rent.

Are dogs allowed in vacation rentals in Oak Bluffs?

In case if you are traveling with a pet in Oak Bluffs - 18% of vacation homes allow pets.

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