Oak Bluffs Holiday Rentals

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Our top choices for Oak Bluffs holiday rentals

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 NZ$1,539
includes taxes & fees
1 Jan - 2 Jan 2026
A NOSTALGIC SPACE! 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 NZ$2,087
includes taxes & fees
1 Jan - 2 Jan 2026
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
9.4 out of 10, Exceptional, (88)
"Very happy. Thank you for the stay."
United States
Gillian S.
The price is NZ$1,150
includes taxes & fees
1 Jan - 2 Jan 2026
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 NZ$1,101
includes taxes & fees
1 Jan - 2 Jan 2026
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

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

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 NZ$256
includes taxes & fees
4 Jan - 5 Jan 2026
InnSeason Resorts Captain's Quarters
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 NZ$643
includes taxes & fees
1 Jan - 2 Jan 2026
The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!
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 NZ$926
includes taxes & fees
16 Jan - 17 Jan 2026
Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area
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 NZ$641
includes taxes & fees
1 Jan - 2 Jan 2026
Spacious and Bright , Very Close to Beach!
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 NZ$346
includes taxes & fees
1 Jan - 2 Jan 2026
Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath
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 NZ$1,147
includes taxes & fees
1 Jan - 2 Jan 2026
Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC
9.4 out of 10, Exceptional, (10)
"Great location"
United States
Robert C.
The price is NZ$662
includes taxes & fees
6 Jan - 7 Jan 2026
The SandDollar Suite - Private Deck with Gorgeous Views of Onset Beach
9.8 out of 10, Exceptional, (24)
"The property was very nice and in a great location."
United States
Judith H.
The price is NZ$731
includes taxes & fees
9 Jan - 10 Jan 2026
Amazing Onset Getaway in the Starfish Suite
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 NZ$390
includes taxes & fees
1 Jan - 2 Jan 2026
Welcome to the Cape! Cute, quiet and clean apartment ready for your stay.
10.0 out of 10, Exceptional, (211)
"Nicely furnished and very comfortable. Very private, yet convenient location. "
United States
John H.
The price is NZ$854
includes taxes & fees
4 Jan - 5 Jan 2026
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
9.8 out of 10, Exceptional, (24)
"Property was perfectly kept and very comfortable. "
United States
Steve D.
The price is NZ$989
includes taxes & fees
5 Jan - 6 Jan 2026
The Seashell Cove - Martha's Vineyard

Holiday Home in Falmouth

Falmouth Oasis
2.0 star property
The price is NZ$749
includes taxes & fees
19 Jan - 20 Jan 2026
Falmouth Oasis

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 NZ$1,072
includes taxes & fees
1 Jan - 2 Jan 2026
Hyannis Hideaway in Cape Cod
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 NZ$1,902
includes taxes & fees
7 Jan - 8 Jan 2026
Lakefront Stunning Cape Cod Views w Private Lake Beach - Backyard is the Lake !
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 NZ$689
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.
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Top Oak Bluffs Hotel Reviews

Find out more about Oak Bluffs

Everything you need to know about Oak Bluffs holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oak Bluffs holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oak Bluffs holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Oak Bluffs holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oak Bluffs. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oak Bluffs holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oak Bluffs holiday rentals we have selected for you start as low as NZ$256 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Oak Bluffs rentals

At Expedia, we put the best Oak Bluffs holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Oak Bluffs rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oak Bluffs holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oak Bluffs. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.