A row of colorful, historic houses with a central path.

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Our top choices for Oak Bluffs holiday rentals

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.4 out of 10, Exceptional, (6 reviews)
"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 £948
includes taxes & fees
30 Jul - 31 Jul
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

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, (92 reviews)
"Great place to stay in Oak Bluffs"
United States
Stephen S.
The price is £565
includes taxes & fees
10 Jul - 11 Jul
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Oak Bluffs
9.6 out of 10, Exceptional, (10 reviews)
"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 £1,704
includes taxes & fees
21 Jul - 22 Jul
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Beautiful Beachfront “Oasis by the Sea” in the Heart of Oak Bluffs!

Beautiful Beachfront “Oasis by the Sea” in the Heart of Oak Bluffs!
Oak Bluffs
9.8 out of 10, Exceptional, (58 reviews)
"Property was well taken care of, very clean with great location!"
United States
Stephanie
The price is £672
includes taxes & fees
9 Jul - 10 Jul
Beautiful Beachfront “Oasis by the Sea” in the Heart of Oak Bluffs!

Beautiful Estate with salt water pool & pond with kayaks

Beautiful Estate with salt water pool & pond with kayaks
Oak Bluffs
10.0 out of 10, Exceptional, (1 review)
"I can’t say enough about this beautiful property. pictures don’t do any justice for this piece of heaven. The flowers were everywhere , it’s so apparent that the property owners take such pride in this beautiful property. The place was spotless when we walked in the door. We met the owners on arrival , they surprised us with a beautiful ballon to celebrate my 50th birthday. My family enjoyed the pool and the fun Tiki. The outdoor fireplace was inviting after the sun went down. I was a little...
United States
Miriam D.
The price is £3,029
includes taxes & fees
21 Jul - 22 Jul
Beautiful Estate with salt water pool & pond with kayaks

4+ Bedroom. Great location. Meadow View Rd. Oak Bluffs.

4+ Bedroom. Great location. Meadow View Rd. Oak Bluffs.
Oak Bluffs
10.0 out of 10, Exceptional, (46 reviews)
"We had an excellent time! The home was conveniently located and well stocked for our week long stay with 9 adults and 1 infant. We hope to visit and stay here again!"
United States
Joanne P.
4+ Bedroom. Great location. Meadow View Rd. Oak Bluffs.

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
9.2 out of 10, Wonderful, (89 reviews)
"The location of this property cannot be beat! Our second time staying here."
United States
Ashley S.
The price is £565
includes taxes & fees
13 Jul - 14 Jul
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

Small One Bedroom Private Cottage on Large Quiet Property.

Small One Bedroom Private Cottage on Large Quiet Property.
Tisbury
10.0 out of 10, Exceptional, (15 reviews)
"Nice, quaint cottage. Perfect for a couple's getaway! Location was convenient for walking to shops and restaurants."
United States
Randy T.
The price is £387
includes taxes & fees
27 Jul - 28 Jul
Small One Bedroom Private Cottage on Large Quiet Property.

Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
New Seabury
8.6 out of 10, Excellent, (93 reviews)
"This was the perfect home for our weekend getaway! Joyce was wonderful to work with. Perfect location and beautiful home, just what we needed!"
United States
Courtney R.
The price is £460
includes taxes & fees
12 Jul - 13 Jul
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

The Sky-High Beach House: Panoramic Waterfront views

The Sky-High Beach House: Panoramic Waterfront views
Fairhaven
The price is £376
includes taxes & fees
14 Jul - 15 Jul
The Sky-High Beach House: Panoramic Waterfront views

1 Mi to Ferry: 'sea Street Cottage' in Hyannis

1 Mi to Ferry: 'sea Street Cottage' in Hyannis
3.0 star property
Hyannis
8.0 out of 10, Very good, (1 review)
"The cottage is in a great location close to Main Street and the harbor. Easy parking at the cottage and it’s in a walkable area. Decor is cute and nautical, but it does feel like the cottage is missing a few things. It sleeps 4, but there is not enough seating for 4 in the living room. An additional comfortable chair would be nice. A stackable washer and dryer would also be great, but there is very little space for anything- we even had trouble finding spots for our luggage. The fridge door...
United States
Christa
The price is £289
includes taxes & fees
21 Jul - 22 Jul
1 Mi to Ferry: 'sea Street Cottage' in Hyannis

2 Mi to Dowses Beach! Couples Haven in Osterville

2 Mi to Dowses Beach! Couples Haven in Osterville
Osterville
The price is £197
includes taxes & fees
15 Jul - 16 Jul
2 Mi to Dowses Beach! Couples Haven in Osterville

Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!
Fairhaven
9.6 out of 10, Exceptional, (35 reviews)
"We were looking for a weekend away from home, and we're lucky to find this place available. We got great recommendations for places to eat nearby, and were able to enjoy the area. We'd stay here again!"
United States
Zachary S.
The price is £379
includes taxes & fees
4 Aug - 5 Aug
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

Spacious and Bright , Very Close to Beach!

Spacious and Bright , Very Close to Beach!
Onset
9.6 out of 10, Exceptional, (25 reviews)
"Amazing location, clean, spacious suite, great communication with the host, overall a great experience! "
United States
Bernadette C.
The price is £380
includes taxes & fees
14 Jul - 15 Jul
Spacious and Bright , Very Close to Beach!

5 Mi to Beach: Cape Cod Getaway w/ Grill

5 Mi to Beach: Cape Cod Getaway w/ Grill
Sandwich
9.6 out of 10, Exceptional, (37 reviews)
"Great location & comfortable house for exploring Cape Cod & surrounding area"
United States
Linda
The price is £444
includes taxes & fees
20 Jul - 21 Jul
5 Mi to Beach: Cape Cod Getaway w/ Grill

Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth

Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth
Falmouth
9.6 out of 10, Exceptional, (14 reviews)
"Really beautiful place with a lot of space and a very helpful host"
United States
Gokul K.
The price is £872
includes taxes & fees
23 Jul - 24 Jul
Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth

Near Old Silver Beach Falmouth-Two bedroom, private bathroom and kitchenette

Near Old Silver Beach Falmouth-Two bedroom, private bathroom and kitchenette
Falmouth
8.4 out of 10, Very good, (29 reviews)
"Very nice location in North Falmouth where things feel timeless. The only disadvantage was there is no living/sitting room. You can sit in the kitchen or be in the bedrooms. Host was attentive and available."
United States
Michelle
Near Old Silver Beach Falmouth-Two bedroom, private bathroom and kitchenette

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

The SandDollar Suite - Private Deck with Gorgeous Views of Onset Beach
Onset
9.4 out of 10, Exceptional, (10 reviews)
"Top floor is the best! "
United States
Alyssa A.
The price is £397
includes taxes & fees
16 Jul - 17 Jul
The SandDollar Suite - Private Deck with Gorgeous Views of Onset Beach

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

The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!
Onset
9.8 out of 10, Exceptional, (28 reviews)
"This place is beautiful, so clean and close to great restaurants and a clean and beautiful beach. We went to celebrate a birthday and it was perfect! "
United States
Larisa
The price is £379
includes taxes & fees
12 Jul - 13 Jul
The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!

Serene Haven w/ No Shared Spaces | Cape Cod

Serene Haven w/ No Shared Spaces | Cape Cod
Marston Mills
10.0 out of 10, Exceptional, (16 reviews)
"Marston Hills is a great location for getting to many great areas of Cape Cod. The house was very clean and nicely furnished. "
United States
Dana S.
The price is £336
includes taxes & fees
2 Aug - 3 Aug
Serene Haven w/ No Shared Spaces | Cape Cod
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, apart-hotels, 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 £431 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. 

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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 garden, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Other favourite homes for rent in Oak Bluffs are Quaint, ranch style home in Oak Bluffs with central air and Bright old-world cottage with two porches & large yard - walk to town & beaches.

How many holiday rentals will I find in Oak Bluffs?

Choose from 270 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 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.