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

Vacation rentals in Oak Bluffs

Browse 1,501 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

    • 2 mi
    • 3 mi
    • Any

  • 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 most Recommended Vacation Rentals in Oak Bluffs

Discover your ideal Oak Bluffs vacation rental with real-time comparisons of 1,501 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Oak Bluffs
House ∙ 4 guests ∙ 2 bedrooms

Children-friendly vacation home with terrace & barbecue

Oak Bluffs, Dukes County, Massachusetts, United States
This Oak Bluffs house rental features a kitchen, family-friendly layout, and parking, perfect for a memorable getaway with friends.
from $377
per night
Outstanding(6 ratings)
from $377
per night
View deal
House Oak Bluffs
House ∙ 13 guests ∙ 6 bedrooms

Fully equipped vacation home with barbecue & terrace | Beach nearby

Oak Bluffs, Dukes County, Massachusetts, United States
This Oak Bluffs house rental features a kitchen, balcony, and parking, perfect for accommodating up to 13 guests.
from $1,194
per night
Outstanding(16 ratings)
from $1,194
per night
View deal
House Oak Bluffs
House ∙ 18 guests ∙ 9 bedrooms

House with garden, terrace & BBQ

Oak Bluffs, Dukes County, Massachusetts, United States
This Oak Bluffs house rental features a kitchen, yard, and balcony, perfect for family gatherings with space for 18 guests.
from $1,517
per night
Outstanding(5 ratings)
from $1,517
per night
View deal
House Oak Bluffs
House ∙ 10 guests ∙ 5 bedrooms

Children-friendly house with BBQ & patio | Close to the beach

Oak Bluffs, Dukes County, Massachusetts, United States
This Oak Bluffs house rental features a kitchen, balcony, and parking, perfect for accommodating up to 10 guests.
from $1,187
per night
Outstanding(28 ratings)
from $1,187
per night
View deal
Cabin Oak Bluffs
Cabin ∙ 8 guests ∙ 5 bedrooms

Cottage with BBQ, terrace & yard | Nature view

Oak Bluffs, Dukes County, Massachusetts, United States
This Oak Bluffs cabin features a kitchen, yard, and parking, perfect for family gatherings of up to eight guests.
from $639
per night
Outstanding(40 ratings)
from $639
per night
View deal
House Oak Bluffs
House ∙ 8 guests ∙ 4 bedrooms

Family-oriented vacation home with patio, barbeque & garden | Suitable for remote work

Oak Bluffs, Dukes County, Massachusetts, United States
This waterfront house rental in Oak Bluffs features a kitchen, yard, and parking, perfect for accommodating up to 8 guests.
from $726
per night
Outstanding(21 ratings)
from $726
per night
View deal
House Oak Bluffs
House ∙ 9 guests ∙ 4 bedrooms

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

Oak Bluffs, Dukes County, Massachusetts, United States
This Edgartown house rental for nine features a cozy fireplace, a kitchen, and pet-friendly spaces, perfect for family getaways.
from $402
per night
Outstanding(44 ratings)
from $402
per night
View deal
House Oak Bluffs
House ∙ 8 guests ∙ 4 bedrooms

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

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 $428
per night
Outstanding(95 ratings)
from $428
per night
View deal
House Oak Bluffs
House ∙ 6 guests ∙ 3 bedrooms

House with terrace, barbeque & jacuzzi | City view

Oak Bluffs, Dukes County, Massachusetts, United States
This Oak Bluffs house rental features a kitchen, hot tub, balcony, and parking, perfect for a getaway with up to six guests.
from $406
per night
Excellent(32 ratings)
from $406
per night
View deal
House Oak Bluffs
House ∙ 12 guests ∙ 6 bedrooms

Fully equipped wonderful vacation home with BBQ, patio & yard | Suitable for remote work

Oak Bluffs, Dukes County, Massachusetts, United States
This house rental in Vineyard Haven offers beach access, a yard, and waterfront views, accommodating up to 12 guests.
from $1,006
per night
Outstanding(27 ratings)
from $1,006
per night
View deal
House Oak Bluffs
House ∙ 12 guests ∙ 5 bedrooms

Family-oriented wonderful house with patio & BBQ

Oak Bluffs, Dukes County, Massachusetts, United States
This Oak Bluffs house rental features a fireplace, a kitchen, and parking, accommodating up to 12 guests for a perfect getaway.
from $934
per night
Outstanding(54 ratings)
from $934
per night
View deal
House Oak Bluffs
House ∙ 6 guests ∙ 3 bedrooms

Fully equipped beautiful house with barbeque & patio | Nature view

Oak Bluffs, Dukes County, Massachusetts, United States
This Oak Bluffs house rental features a kitchen, balcony, and parking, perfect for a getaway with family or friends.
from $540
per night
Very good(52 ratings)
from $540
per night
View deal
House Oak Bluffs
House ∙ 10 guests ∙ 5 bedrooms

House with yard, terrace & grill

Oak Bluffs, Dukes County, Massachusetts, United States
This house rental in Oak Bluffs offers a kitchen, balcony, yard, and parking, perfect for families and groups of up to 10.
from $1,285
per night
Outstanding(10 ratings)
from $1,285
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 $212
per night
Excellent(51 ratings)
from $212
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
This Edgartown house rental features a hot tub, fireplace, and yard, accommodating up to 15 guests for a memorable getaway.
from $1,513
per night
Outstanding(46 ratings)
from $1,513
per night
View deal

Vacation homes and rentals with a yard

House Oak Bluffs
from $642
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
Yard
View deal
House Oak Bluffs
from $303
per night
House ∙ 8 guests ∙ 3 bedrooms

Children-friendly lovely house with BBQ, garden & patio | Dogs allowed

4.7
Excellent(96 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Yard
View deal
House Oak Bluffs
from $849
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
Yard
View deal
See all offers

Vacation houses with Balconies or Patios

House Oak Bluffs
from $150
per night
House ∙ 7 guests ∙ 3 bedrooms

House with patio & BBQ

5.0
Outstanding(4 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Balcony/Patio
View deal
House Oak Bluffs
from $758
per night
House ∙ 10 guests ∙ 5 bedrooms

Vacation home with yard, barbecue & patio

5.0
Outstanding(109 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Balcony/Patio
View deal
Cabin Oak Bluffs
from $721
per night
Cabin ∙ 5 guests ∙ 3 bedrooms

Cottage with barbeque, terrace & garden | City view

4.9
Outstanding(30 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Balcony/Patio
View deal
See all offers

Vacation rentals and apartments with air conditioning

Cabin Oak Bluffs
from $1,082
per night
Cabin ∙ 10 guests ∙ 6 bedrooms

Cottage with yard & barbeque

5.0
Outstanding(1 rating)
Oak Bluffs, Dukes County, Massachusetts, United States
Air conditioning
View deal
House Oak Bluffs
from $421
per night
House ∙ 6 guests ∙ 3 bedrooms

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

4.5
Excellent(47 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Air conditioning
View deal
House Oak Bluffs
from $1,718
per night
House ∙ 14 guests ∙ 7 bedrooms

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

5.0
Outstanding(44 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 $156
per night
House ∙ 6 guests ∙ 3 bedrooms

Pleasant house with yard & terrace

3.3
(36 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
View deal
House Oak Bluffs
from $377
per night
House ∙ 7 guests ∙ 3 bedrooms

Fully equipped beautiful vacation home with barbecue, garden & pool | Nature view | Perfect for remote work

4.8
Outstanding(46 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
View deal
House Oak Bluffs
from $543
per night
House ∙ 8 guests ∙ 4 bedrooms

Children-friendly vacation home with garden, terrace & grill | Pet-friendly

5.0
Outstanding(79 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

Apartment Oak Bluffs
from $388
per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Family-oriented apartment | Beach view | Beach nearby

4.9
Outstanding(95 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
View deal
House Oak Bluffs
from $1,160
per night
House ∙ 9 guests ∙ 4 bedrooms

House with jacuzzi, barbeque & yard | City view

5.0
Outstanding(64 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
View deal
Apartment Oak Bluffs
from $235
per night
Apartment ∙ 4 guests ∙ 1 bedroom

Rental apartment with terrace & grill | City view | Beach nearby | Pets allowed

5.0
Outstanding(59 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 1,501 rentals
💳 Possible discounts up to 16%
🌙 Nightly prices starting at $210
⭐ Popular amenities Air conditioning, Pets allowed and Internet
🐾 Pet friendly homes 280 homes
🏊 Vacation rentals with pools 271 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 $210 per night. Average prices for house rentals are $1,203 per night. Cottages in Oak Bluffs cost $852 per night on average.

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

Currently there are 1,501 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 271 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 - 19% of vacation homes allow pets.

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