Oak Bluffs Holiday Rentals

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Holiday Rentals in Oak Bluffs

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

Oak Bluffs
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 AU$1,374
includes taxes & fees
16 Dec - 17 Dec
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Oak Bluffs
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 AU$1,864
includes taxes & fees
16 Dec - 17 Dec
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

Oak Bluffs
9.4 out of 10, Exceptional, (88)
"Very happy. Thank you for the stay."
United States
Gillian S.
The price is AU$763
includes taxes & fees
16 Dec - 17 Dec
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

Oak Bluffs
9.4 out of 10, Exceptional, (91)
"Awesome view"
United States
Dave B.
The price is AU$763
includes taxes & fees
16 Dec - 17 Dec
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

The Club at New Seabury

3.5 star property
New Seabury
9.0 out of 10, Wonderful, (338)
"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 price is AU$256
includes taxes & fees
16 Dec - 17 Dec
The Club at New Seabury

Steps from Marina, beach, restaurants!

Wareham
9.8 out of 10, Exceptional, (12)
"Beautiful space, wonderful location, amazing host. If I could give 100 stars I would! "
United States
Jaimie
The price is AU$363
includes taxes & fees
4 Dec - 5 Dec
Steps from Marina, beach, restaurants!

Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

Barnstable
8.6 out of 10, Excellent, (8)
"This was an amazing property and our host was awesome and checked in to make sure everything was going well. Would definitely stay here again! Thank you! "
United States
Kim
The price is AU$800
includes taxes & fees
16 Dec - 17 Dec
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

The SandDollar Suite - Private Deck with Gorgeous Views of Onset Beach

Onset
9.4 out of 10, Exceptional, (9)
"Great location"
United States
Robert C.
The price is AU$649
includes taxes & fees
4 Dec - 5 Dec
The SandDollar Suite - Private Deck with Gorgeous Views of Onset Beach

The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!

Onset
9.8 out of 10, Exceptional, (28)
"The space was perfect for our needs. The beds were comfortable, the rooms were very clean. If needed, we would definitely come back to this rental."
United States
Lynn
The price is AU$649
includes taxes & fees
4 Dec - 5 Dec
The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!

Spacious and Bright , Very Close to Beach!

Onset
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 AU$649
includes taxes & fees
4 Dec - 5 Dec
Spacious and Bright , Very Close to Beach!

Amazing Onset Getaway in the Starfish Suite

Onset
9.8 out of 10, Exceptional, (23)
"Location was unbelievable-right next to beach"
United States
Terry B.
The price is AU$706
includes taxes & fees
4 Dec - 5 Dec
Amazing Onset Getaway in the Starfish Suite

Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC

Barnstable
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 AU$1,031
includes taxes & fees
4 Dec - 5 Dec
Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC

Newly Renovated Martha's Vineyard Vacation Rental!

Katama
9.6 out of 10, Exceptional, (47)
"Stay was nice, property is very clean and in close distance to most everything. Just wish they had made the lack of towels and linens more obvious in the listing. "
United States
James L.
The price is AU$933
includes taxes & fees
16 Dec - 17 Dec
Newly Renovated Martha's Vineyard Vacation Rental!

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Falmouth
10.0 out of 10, Exceptional, (209)
"We had a great stay. House is spacious, clean and well-stocked with everything we needed. We loved that we were able to walk to downtown shops and restaurants, the ferry to Martha’s Vineyard and the beach. Would definitely stay here again. "
United States
Ava B.
The price is AU$758
includes taxes & fees
16 Dec - 17 Dec
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Hyannis with Waterview [3bd]

Barnstable
7.0 out of 10, Good, (2)
"We wanted a place close to town so we could walk to restaurants and downtown. We each had our own room. We watched movies and hung out when we were not exploring the area. There was a lovely park just a few blocks away and a very good sidewalk for walking. We had our own parking lot which was nice. Everything was very nicely kept. "
United States
Kathy J.
The price is AU$978
includes taxes & fees
16 Dec - 17 Dec
Hyannis with Waterview [3bd]

The Seashell Cove - Martha's Vineyard

Katama
9.8 out of 10, Exceptional, (24)
"Property was perfectly kept and very comfortable. "
United States
Steve D.
The price is AU$887
includes taxes & fees
8 Dec - 9 Dec
The Seashell Cove - Martha's Vineyard

Spring Escape in Hatchville – Sleeps 6 + Dogs!

Falmouth
10.0 out of 10, Exceptional, (11)
"The house is very nice and clean and Brian was extremely communicative and flexible with a late checkout. Would definitely stay again"
United States
Michael B.
The price is AU$1,086
includes taxes & fees
4 Dec - 5 Dec
Spring Escape in Hatchville – Sleeps 6 + Dogs!

Coastal chic meets French Provençal in this newly renovated oceanfront home.

East Falmouth
10.0 out of 10, Exceptional, (88)
"Great stay! "
United States
Michael M.
The price is AU$1,380
includes taxes & fees
8 Dec - 9 Dec
Coastal chic meets French Provençal in this newly renovated oceanfront home.

Welcome to the Cape! Cute, quiet and clean apartment ready for your stay.

Bourne
9.8 out of 10, Exceptional, (20)
"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 AU$327
includes taxes & fees
16 Dec - 17 Dec
Welcome to the Cape! Cute, quiet and clean apartment ready for your stay.

Cozy efficiency apartment/heated pool

Chilmark
9.6 out of 10, Exceptional, (21)
"We loved this property and would love to return!"
United States
Clifford L.
The price is AU$711
includes taxes & fees
31 Dec - 1 Jan 2026
Cozy efficiency apartment/heated pool
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 favourite 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 depend 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 AU$256 per night. Entering your travel dates in the search wizard might find you 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?

Ocean Park and Oak Bluffs Town Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Oak Bluffs Fishing Pier. 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.