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

Holiday Rentals in Oak Bluffs

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Our top choices for Oak Bluffs holiday rentals

Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is €1,474
includes taxes & fees
3 Aug - 4 Aug
Walk to Beach! Oak Bluffs Home & Studio

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 €1,144
includes taxes & fees
16 Jul - 17 Jul
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
Oak Bluffs
9.8 out of 10, Exceptional, (6 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
The price is €1,809
includes taxes & fees
27 Jul - 28 Jul
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

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 €1,959
includes taxes & fees
21 Jul - 22 Jul
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Brand New Guest house

Brand New Guest house
Oak Bluffs
10.0 out of 10, Exceptional, (4 reviews)
"This is a new, beautiful and tastefully decorated 2 bedroom one bathroom house with a really nice big yard. Owner was very responsive and We had everything we needed for an enjoyable stay!"
United States
Elizabeth O.
The price is €878
includes taxes & fees
20 Jul - 21 Jul
Brand New Guest house

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 €665
includes taxes & fees
21 Jul - 22 Jul
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

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 €3,589
includes taxes & fees
19 Jul - 20 Jul
Beautiful Estate with salt water pool & pond with kayaks

Perfect location! By Beach, Harbor & Town! Gorgeous Gingerbread Upstairs Aptmt

Perfect location! By Beach, Harbor & Town! Gorgeous Gingerbread Upstairs Aptmt
Oak Bluffs
10.0 out of 10, Exceptional, (46 reviews)
"Great accommodations and a perfect location for the beach, shopping and great food."
United States
Hugh M.
Perfect location! By Beach, Harbor & Town! Gorgeous Gingerbread Upstairs Aptmt

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 €666
includes taxes & fees
22 Jul - 23 Jul
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Oak Bluffs
6.8 out of 10, (9 reviews)
"This house was perfect. Super cute interior, well outfitted beds, plenty of space for our large family (2 adults, 4 kids, 1 small dog) - bonus points for the big laundry machines. Extra points for the super helpful and responsive host who went out of his way for us - even when I was messaging late at night on a Saturday after my daughter took a fall in Edgartown and had to be transported to Vineyard Hospital by ambulance. We will definitely rent this house again. Highly recommend!! "
United States
Nicole L.
The price is €886
includes taxes & fees
24 Jul - 25 Jul
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (363 reviews)
"The condo had everything we needed, and was clean, however there were a lot of ants on the main floor, mostly in the kitchen. This should definitely be looked into and maybe some traps set. There was a washer/dryer which was great and room service each day to change towels."
Canada
Rylea
The price is €506
includes taxes & fees
20 Jul - 21 Jul
The Club at New Seabury

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 €446
includes taxes & fees
27 Jul - 28 Jul
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach

Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach
New Seabury
10.0 out of 10, Exceptional, (9 reviews)
"Great place"
United States
Aaron Q.
The price is €1,330
includes taxes & fees
16 Jul - 17 Jul
Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach

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

The SandDollar Suite - Private Deck with Gorgeous Views of Onset Beach
Onset
9.6 out of 10, Exceptional, (11 reviews)
"Great location"
United States
Robert C.
The price is €479
includes taxes & fees
16 Jul - 17 Jul
The SandDollar Suite - Private Deck with Gorgeous Views of Onset Beach

5 Mi to Beach: Cape Cod Getaway w/ Grill

5 Mi to Beach: Cape Cod Getaway w/ Grill
3.0 star property
Sandwich
The price is €524
includes taxes & fees
20 Jul - 21 Jul
5 Mi to Beach: Cape Cod Getaway w/ Grill

4-bedroom house in lovely Edgartown..Centrally located

4-bedroom house in lovely Edgartown..Centrally located
Edgartown
10.0 out of 10, Exceptional, (2 reviews)
"Absolutely incredible stay! The host is so kind and helpful. House was very clean. Truly everything you need inside for cooking and beach fun! PERFECT location really centrally located to both edgartown and oak bluffs. Located in a quiet neighborhood near Felix Neck with lots of walking trails, which was very nice! Could not recommend this place more!"
United States
Katelyn W.
The price is €1,283
includes taxes & fees
21 Jul - 22 Jul
4-bedroom house in lovely Edgartown..Centrally located

Spacious and Bright , Very Close to Beach!

Spacious and Bright , Very Close to Beach!
Onset
9.8 out of 10, Exceptional, (26 reviews)
"Amazing location, clean, spacious suite, great communication with the host, overall a great experience! "
United States
Bernadette C.
The price is €478
includes taxes & fees
19 Jul - 20 Jul
Spacious and Bright , Very Close to Beach!

WATERFRONT Downtown Cottage w/ Beach

WATERFRONT Downtown Cottage w/ Beach
Tisbury
10.0 out of 10, Exceptional, (50 reviews)
"Very beautiful, very clean with incredible views of the Vineyard Haven harbor views"
United States
John M.
The price is €1,230
includes taxes & fees
31 Jul - 1 Aug
WATERFRONT Downtown Cottage w/ Beach

New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!

New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!
Barnstable
10.0 out of 10, Exceptional, (33 reviews)
"It was a great stay and clean home. Recommend people to stay here"
United States
Charbel T.
The price is €1,180
includes taxes & fees
19 Jul - 20 Jul
New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!

Chappy cottage with private beach

Chappy cottage with private beach
Edgartown
10.0 out of 10, Exceptional, (18 reviews)
"What a gorgeous location, my family and I had a wonderful time on Chappy, will definitely be back!"
United States
Clinton G.
The price is €1,418
includes taxes & fees
30 Jul - 31 Jul
Chappy cottage with private beach
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 €506 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 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 271 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.