Photo by William Keller

Oak Bluffs Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
16 Jan - 18 Jan
In two months
27 Feb - 1 Mar
In three months
27 Mar - 29 Mar
In four months
24 Apr - 26 Apr

Our top choices for Oak Bluffs holiday rentals

TV, fireplace, books
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

Holiday Home in Oak Bluffs

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
9.4 out of 10, Exceptional, (3)
"This house was perfect for our getaway. Rebecca, the host, was extremely responsive and helpful during our trip. The house was as advertised. It was clean, well equipped, and the location was perfect as well "
United States
Louis R.
The price is HK$2,721
HK$6,947 total
includes taxes & fees
3 Jan - 4 Jan 2026
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Interior
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Holiday Home in Oak Bluffs

MOST CHIC SPOT! Your Martha's Vineyard Getaway!
10.0 out of 10, Exceptional, (7)
"Our kids and their friends had so much fun in the beautifully finished basement. Easy access to beach and ferry, would love to go back every year, the host was wonderful."
United States
Swathanthra M.
The price is HK$4,276
HK$9,422 total
includes taxes & fees
3 Jan - 4 Jan 2026
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Smart TV
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

Apartment in Oak Bluffs

Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
9.4 out of 10, Exceptional, (88)
"Very happy. Thank you for the stay."
United States
Gillian S.
The price is HK$3,148
HK$5,149 total
includes taxes & fees
3 Jan - 4 Jan 2026
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
Interior
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

Apartment in Oak Bluffs

Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
9.4 out of 10, Exceptional, (91)
"Great place to stay in Oak Bluffs"
United States
Stephen S.
The price is HK$2,974
HK$4,989 total
includes taxes & fees
9 Jan - 10 Jan 2026
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Private beach nearby, beach bar
The Club at New Seabury

Condo resort in New Seabury

The Club at New Seabury
3.5 star property
9.0 out of 10, Wonderful, (341)
"Very relaxing, loved the different clubs available; beach, pool, tennis, playground for the little ones, bars and food. Some shops were closed due to being off season, but still enjoyed our stay. Looking forward to booking again "
United States
Jose O.
The Club at New Seabury
On the beach, white sand
InnSeason Resorts Captain's Quarters

Aparthotel in Falmouth Heights

InnSeason Resorts Captain's Quarters
3.5 star property
9.8 out of 10, Exceptional, (193)
"Best scenery ever !"
United States
Jacqueline
The price is HK$1,008
HK$1,153 total
includes taxes & fees
4 Jan - 5 Jan 2026
InnSeason Resorts Captain's Quarters
Exterior
The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!

Apartment in Onset

The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!
9.8 out of 10, Exceptional, (28)
"We’ve never to the area before and loved it! Location is perfect!!! Place was clean and well stocked. Host was amazing! This was a beautiful getaway can’t wait to be back! "
United States
maria O.
The price is HK$1,112
HK$2,997 total
includes taxes & fees
6 Jan - 7 Jan 2026
The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!
Beach
Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area

Holiday Home in Falmouth

Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area
10.0 out of 10, Exceptional, (8)
"This property was beautiful! The hosts were excellent and were always available to message. I would recommend a stay at this home."
United States
Lisa Mason D.
The price is HK$1,360
HK$4,182 total
includes taxes & fees
16 Jan - 17 Jan 2026
Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area
Exterior
Spacious and Bright , Very Close to Beach!

Apartment in Onset

Spacious and Bright , Very Close to Beach!
9.6 out of 10, Exceptional, (22)
"Amazing location, clean, spacious suite, great communication with the host, overall a great experience! "
United States
Bernadette C.
The price is HK$1,112
HK$2,988 total
includes taxes & fees
4 Jan - 5 Jan 2026
Spacious and Bright , Very Close to Beach!
Beach nearby
Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath

Apartment in Falmouth

Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath
8.2 out of 10, Very good, (24)
"Wonderful stay, had everything we needed, Joy was very receptive to our messages. Thanks so much!"
United States
Alex K.
The price is HK$762
HK$1,557 total
includes taxes & fees
10 Jan - 11 Jan 2026
Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath
Terrace/patio
Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC

Holiday Home in Barnstable

Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC
10.0 out of 10, Exceptional, (4)
"Very nice property in a quiet and convenient location. Private backyard with outdoor shower. Interior was completely updated with very nice furnishings and appliances. All in all a great home that we will definitely return to. "
United States
Jim C.
The price is HK$2,052
HK$5,178 total
includes taxes & fees
1 Jan - 2 Jan 2026
Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC
Exterior
The SandDollar Suite - Private Deck with Gorgeous Views of Onset Beach

Apartment in Onset

The SandDollar Suite - Private Deck with Gorgeous Views of Onset Beach
9.4 out of 10, Exceptional, (10)
"Great location"
United States
Robert C.
The price is HK$1,112
HK$2,979 total
includes taxes & fees
6 Jan - 7 Jan 2026
The SandDollar Suite - Private Deck with Gorgeous Views of Onset Beach
Exterior
Amazing Onset Getaway in the Starfish Suite

Condo in Onset

Amazing Onset Getaway in the Starfish Suite
9.8 out of 10, Exceptional, (24)
"The property was very nice and in a great location."
United States
Judith H.
The price is HK$1,182
HK$3,275 total
includes taxes & fees
4 Jan - 5 Jan 2026
Amazing Onset Getaway in the Starfish Suite
Exterior
Welcome to the Cape! Cute, quiet and clean apartment ready for your stay.

Apartment in Bourne

Welcome to the Cape! Cute, quiet and clean apartment ready for your stay.
10.0 out of 10, Exceptional, (21)
"This is a wonderful place to stay with the amenities of home. Spacious, private, with lots of places nearby to see and explore."
United States
Becky P.
The price is HK$1,360
HK$1,762 total
includes taxes & fees
1 Jan - 2 Jan 2026
Welcome to the Cape! Cute, quiet and clean apartment ready for your stay.
Fridge, microwave, oven, stovetop
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Holiday Home in Falmouth

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
10.0 out of 10, Exceptional, (211)
"Nicely furnished and very comfortable. Very private, yet convenient location. "
United States
John H.
The price is HK$1,259
HK$3,799 total
includes taxes & fees
12 Jan - 13 Jan 2026
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Terrace/patio
The Seashell Cove - Martha's Vineyard

Holiday Home in Katama

The Seashell Cove - Martha's Vineyard
9.8 out of 10, Exceptional, (24)
"Property was perfectly kept and very comfortable. "
United States
Steve D.
The price is HK$1,944
HK$4,463 total
includes taxes & fees
5 Jan - 6 Jan 2026
The Seashell Cove - Martha's Vineyard
Exterior
Falmouth Oasis

Holiday Home in Falmouth

Falmouth Oasis
2.0 star property
The price is HK$1,119
HK$3,381 total
includes taxes & fees
5 Jan - 6 Jan 2026
Falmouth Oasis
Paper towels
Hyannis Hideaway in Cape Cod

Holiday Home in Barnstable

Hyannis Hideaway in Cape Cod
10.0 out of 10, Exceptional, (2)
"Awesome private property, close to Main Street and Craigsville beach. My friends and I stay in Hyannis every 4th of July and this home was super accommodating for groups and close to everything. Great stay would recommend. "
United States
Hunter W.
The price is HK$2,766
HK$4,769 total
includes taxes & fees
8 Jan - 9 Jan 2026
Hyannis Hideaway in Cape Cod
Dining
Lakefront Stunning Cape Cod Views w Private Lake Beach - Backyard is the Lake !

Holiday Home in Barnstable

Lakefront Stunning Cape Cod Views w Private Lake Beach - Backyard is the Lake !
10.0 out of 10, Exceptional, (1)
"My family and I thoroughly enjoyed our week long stay at the beautiful property. There were 12 of us and we were extremely comfortable, with plenty of space to gather and sleep. The property sits on a quiet pond, that was perfect for swimming and canoeing. We had our own little piece of paradise. There are canoes for use, several decks for lounging and was within a short distance to various shops and a grocery store just a few minutes away. The host was in constant contact with us, making sure...
United States
Madilynn B.
The price is HK$3,673
HK$8,564 total
includes taxes & fees
1 Jan - 2 Jan 2026
Lakefront Stunning Cape Cod Views w Private Lake Beach - Backyard is the Lake !
Exterior
Sleeps 6 @ New Seabury w/ Pool - All Season Modern Condo!

Condo in New Seabury

Sleeps 6 @ New Seabury w/ Pool - All Season Modern Condo!
10.0 out of 10, Exceptional, (79)
"We were extremely happy with our stay. The condo was beautiful, had everything we needed. Looking forward to coming back again next year for a longer stay"
United States
Beth H.
The price is HK$1,148
HK$3,113 total
includes taxes & fees
3 Jan - 4 Jan 2026
Sleeps 6 @ New Seabury w/ Pool - All Season Modern Condo!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Oak Bluffs Hotel Reviews

Mansion House Inn And Spa

Mansion House Inn And Spa

10/10 Excellent
"Our second time staying. Friendly staff, perfect location, great views. Highly recommend."
Kurt 2-night trip
Posted 3 days ago
Mansion House Inn And Spa

Find out more about Oak Bluffs

Search for holiday rentals in Oak Bluffs on Expedia! You can easily find your home rentals, villas, holiday apartments in Oak Bluffs using one of the methods below:

  • View our selection of featured holiday rentals in Oak Bluffs
  • Use the map to find apartments and other holiday homes in the Oak Bluffs neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Oak Bluffs while they last

Look no further and take a look at our great range of rental properties in Oak Bluffs!

Frequently asked questions

Can I find holiday rentals in Oak Bluffs?

Yes, there are holiday rentals in Oak Bluffs close to Flying Horses Carousel, or you can select a more secluded option if you're looking for a relaxing stay. The shops and waterfront are just a few reasons why tourists like Oak Bluffs. Allow lots of time to check out the beaches and wineries during your visit.

What are some of the best holiday rentals that Oak Bluffs has to offer?

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs: This highly rated holiday home rental in Oak Bluffs is located in the city centre, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Another good choice for your trip to Oak Bluffs is MOST CHIC SPOT! Your Martha's Vineyard Getaway!.

How many holiday rentals will I find in Oak Bluffs?

Choose from 259 Expedia holiday rentals in Oak Bluffs for a memorable holiday.

What can I see and do in Oak Bluffs?

Oak Bluffs Town Beach and Inkwell Beach are a couple of scenic spots to enjoy the outdoors, whereas Cottage Museum is one of the cultural attractions. Other places in town to visit include Circuit Avenue and Oak Bluffs Harbor.

What are holiday rentals like in Oak Bluffs?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oak Bluffs. Holiday rentals feature extras such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for a family trip or a small group gathering.