Oak Bluffs Vacation Rentals

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Our top choices for Oak Bluffs vacation rentals

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.
$1,085 nightly
The price is $1,212
Mar 4 - Mar 5
Total with taxes and fees
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
9.4 out of 10, Exceptional, (91 reviews)
"Great place to stay in Oak Bluffs"
United States
Stephen S.
$446 nightly
The price is $498
Mar 4 - Mar 5
Total with taxes and fees
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
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.
$800 nightly
The price is $894
Mar 4 - Mar 5
Total with taxes and fees
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

Vacation Home in Oak Bluffs

Oak Bluffs - Quiet neighborhood
9.4 out of 10, Exceptional, (43 reviews)
"Perfectly situated!"
United States
Damani B.
$600 nightly
The price is $670
Mar 5 - Mar 6
Total with taxes and fees
Oak Bluffs - Quiet neighborhood
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.
$446 nightly
The price is $498
Mar 4 - Mar 5
Total with taxes and fees
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
8.6 out of 10, Excellent, (91 reviews)
"Property needs a refresh."
United States
Paul B.
$543 nightly
The price is $621
Mar 4 - Mar 5
Total with taxes and fees
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
9.6 out of 10, Exceptional, (22 reviews)
"Amazing location, clean, spacious suite, great communication with the host, overall a great experience! "
United States
Bernadette C.
$345 nightly
The price is $385
Mar 8 - Mar 9
Total with taxes and fees
Spacious and Bright , Very Close to Beach!
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.
$266 nightly
The price is $304
Mar 6 - Mar 7
Total with taxes and fees
Near Old Silver Beach Falmouth/Two bedroom , private bathroom and kitchenette
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.
$852 nightly
The price is $975
Mar 4 - Mar 5
Total with taxes and fees
New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!
10.0 out of 10, Exceptional, (212 reviews)
"This beautiful well-appointed home was the perfect spot for a girlfriend’s getaway. Walkable to the shops and restaurants, nice big rooms for chats, and a great kitchen island to congregate around for breakfast. We loved our time here!"
United States
Annemarie G.
$387 nightly
The price is $443
Mar 4 - Mar 5
Total with taxes and fees
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Vacation Home in Falmouth

Falmouth Oasis
$431 nightly
The price is $493
Mar 4 - Mar 5
Total with taxes and fees
Falmouth Oasis
9.8 out of 10, Exceptional, (12 reviews)
"Beautiful space, wonderful location, amazing host. If I could give 100 stars I would! "
United States
Jaimie
$310 nightly
The price is $346
Mar 4 - Mar 5
Total with taxes and fees
Steps from Marina, beach, restaurants!
10.0 out of 10, Exceptional, (16 reviews)
"We had an amazing time at this beautiful home. Great, clean space to spend an evening visit with friends and family. Great location with easy access around the island. Would highly recommend! "
United States
Jennifer T.
$971 nightly
The price is $1,085
Mar 4 - Mar 5
Total with taxes and fees
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
$381 nightly
The price is $436
Mar 5 - Mar 6
Total with taxes and fees
Entire Hyannis Home - Near Downtown & Beaches
10.0 out of 10, Exceptional, (5 reviews)
"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.
$584 nightly
The price is $668
Mar 5 - Mar 6
Total with taxes and fees
Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC
9.0 out of 10, Wonderful, (2 reviews)
"Very good"
United States
Karl D.
$372 nightly
The price is $416
Mar 4 - Mar 5
Total with taxes and fees
TABOR SUITE, IN THE MARION VILLAGE
10.0 out of 10, Exceptional, (1 review)
"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.
$963 nightly
The price is $1,102
Mar 4 - Mar 5
Total with taxes and fees
Lakefront Stunning Cape Cod Views w Private Lake Beach - Backyard is the Lake !

Vacation Home in Barnstable

Summer 2026 Perfection!
$454 nightly
The price is $520
Mar 4 - Mar 5
Total with taxes and fees
Summer 2026 Perfection!
10.0 out of 10, Exceptional, (8 reviews)
"Great place"
United States
Aaron Q.
$998 nightly
The price is $1,142
Mar 5 - Mar 6
Total with taxes and fees
Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach
9.8 out of 10, Exceptional, (8 reviews)
"Great stay! Great property!"
United States
Liz A.
The Beach Estate, Panoramic Ocean Views, 5700 sqft
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Oak Bluffs vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Oak Bluffs vacation 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 low season months. For more hustle and bustle, you may prefer to visit Oak Bluffs in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $498 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Oak Bluffs rentals

At Expedia, we put the best Oak Bluffs vacation 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 vacation.

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 vacation rentals in Oak Bluffs?

Yes, you can find vacation rentals in Oak Bluffs near Flying Horses Carousel, or you can go with a more secluded option if you're looking for extra privacy while you relax. 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 vacation rentals in Oak Bluffs?

Coastal chic meets French Provençal in this newly renovated oceanfront home. : This vacation home rental outside of Oak Bluffs is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals will I find in Oak Bluffs?

Choose from 248 Expedia vacation rentals in Oak Bluffs for a memorable vacation.

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 vacation rentals like in Oak Bluffs?

Vacation rentals are private accommodations you can reserve for several days or longer in Oak Bluffs. Vacation rentals feature extras such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, vacation rentals can provide a sense of privacy away from public hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for a small group gathering.