Oak Bluffs Holiday Rentals

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Our top choices for Oak Bluffs holiday rentals

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 reviews)
"Great place to stay in Oak Bluffs"
United States
Stephen S.
The price is NZ$848
includes taxes & fees
2 Apr - 3 Apr
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.4 out of 10, Exceptional, (3 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 NZ$1,493
includes taxes & fees
2 Apr - 3 Apr
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

Oak Bluffs - Quiet neighborhood

Oak Bluffs - Quiet neighborhood
Oak Bluffs
9.4 out of 10, Exceptional, (43 reviews)
"Perfectly situated!"
United States
Damani B.
The price is NZ$1,124
includes taxes & fees
25 Apr - 26 Apr
Oak Bluffs - Quiet neighborhood

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Oak Bluffs
10.0 out of 10, Exceptional, (7 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 NZ$2,049
includes taxes & fees
2 Apr - 3 Apr
MOST CHIC SPOT! 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, (88 reviews)
"The location of this property cannot be beat! Our second time staying here."
United States
Ashley S.
The price is NZ$848
includes taxes & fees
2 Apr - 3 Apr
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

Sal's Place

Sal's Place
2.0 star property
Hyannis
The price is NZ$1,006
includes taxes & fees
2 Apr - 3 Apr
Sal's Place

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

Near Old Silver Beach Falmouth/Two bedroom , private bathroom and kitchenette
Falmouth
8.2 out of 10, Very good, (24 reviews)
"Wonderful stay, had everything we needed, Joy was very receptive to our messages. Thanks so much!"
United States
Alex K.
The price is NZ$434
includes taxes & fees
2 Apr - 3 Apr
Near Old Silver Beach Falmouth/Two bedroom , private bathroom and kitchenette

Beachside Village Resort

Beachside Village Resort
3.0 star property
Falmouth
9.4 out of 10, Exceptional, (101 reviews)
"Wonderful location, nice staff!"
United States
Claire
The price is NZ$1,950
includes taxes & fees
18 Apr - 19 Apr
Beachside Village Resort

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, (91 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 NZ$1,056
includes taxes & fees
2 Apr - 3 Apr
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

Summer 2026 Perfection!

Summer 2026 Perfection!
Barnstable
The price is NZ$890
includes taxes & fees
3 Apr - 4 Apr
Summer 2026 Perfection!

Contemporary 4-bedroom ranch style home with AC in charming Falmouth, Cape Cod

Contemporary 4-bedroom ranch style home with AC in charming Falmouth, Cape Cod
Falmouth
The price is NZ$1,249
includes taxes & fees
13 Apr - 14 Apr
Contemporary 4-bedroom ranch style home with AC in charming Falmouth, Cape Cod

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, (8 reviews)
"Great place"
United States
Aaron Q.
The price is NZ$1,943
includes taxes & fees
2 Apr - 3 Apr
Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach

TABOR SUITE, IN THE MARION VILLAGE

TABOR SUITE, IN THE MARION VILLAGE
Marion
9.0 out of 10, Wonderful, (2 reviews)
"Very good"
United States
Karl D.
The price is NZ$869
includes taxes & fees
2 Apr - 3 Apr
TABOR SUITE, IN THE MARION VILLAGE

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, (31 reviews)
"It was a great stay and clean home. Recommend people to stay here"
United States
Charbel T.
The price is NZ$1,640
includes taxes & fees
8 Apr - 9 Apr
New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!

The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard
Katama
9.8 out of 10, Exceptional, (25 reviews)
"Property was perfectly kept and very comfortable. "
United States
Steve D.
The price is NZ$1,394
includes taxes & fees
27 Apr - 28 Apr
The Seashell Cove - Martha's Vineyard

2BR Condo in Cape Cod w/ Patio & Laundry

2BR Condo in Cape Cod w/ Patio & Laundry
Mashpee
The price is NZ$435
includes taxes & fees
26 Apr - 27 Apr
2BR Condo in Cape Cod w/ Patio & Laundry

Falmouth Oasis

Falmouth Oasis
Falmouth
The price is NZ$843
includes taxes & fees
2 Apr - 3 Apr
Falmouth Oasis

Charming studio in tranquil Falmouth with AC

Charming studio in tranquil Falmouth with AC
Falmouth
The price is NZ$388
includes taxes & fees
21 Apr - 22 Apr
Charming studio in tranquil Falmouth with AC

Spacious Lake House for Large Groups w Private Acre+ short path to Lake

Spacious Lake House for Large Groups w Private Acre+ short path to Lake
Barnstable
8.0 out of 10, Very good, (5 reviews)
"Had a great stay here - the hosts were flexible with our early check in and made the whole trip a smooth process! "
United States
Ally D.
The price is NZ$1,922
includes taxes & fees
4 Apr - 5 Apr
Spacious Lake House for Large Groups w Private Acre+ short path to Lake

Charming Chappaquiddick Retreat: Steps from Private Beach & Edgartown's Best!

Charming Chappaquiddick Retreat: Steps from Private Beach & Edgartown's Best!
Edgartown
9.8 out of 10, Exceptional, (16 reviews)
"Overall great experience"
United States
Scott P.
The price is NZ$1,794
includes taxes & fees
2 Apr - 3 Apr
Charming Chappaquiddick Retreat: Steps from Private Beach & Edgartown's Best!
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$848 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.

How many holiday rentals will I find in Oak Bluffs?

Choose from 251 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.