Oak Bluffs Vacation Rentals

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Vacation Rentals in Oak Bluffs

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Oak Bluffs
6.4 out of 10, (31)
"indoor and outdoor comfortable space"
United States
Delores C.
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

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.
$1,060 nightly
The price is $1,184
Dec 2 - Dec 3
Total with taxes and fees
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard

Oak Bluffs
8.2 out of 10, Very Good, (40)
"We loved how the neighborhood was quiet but was still so close to downtown's shops, restaurants, beach, and the bus."
United States
Amanda B.
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard

The quintessential MV home. Now booking for 2026!

Oak Bluffs
9.8 out of 10, Exceptional, (55)
"Just a quick 4 minute drive to downtown. Listing was accurate and place was clean!"
United States
Jennifer D.
The quintessential MV home. Now booking for 2026!

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.
$446 nightly
The price is $498
Dec 2 - Dec 3
Total with taxes and fees
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

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.
$800 nightly
The price is $894
Dec 2 - Dec 3
Total with taxes and fees
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

Beautiful Estate with salt water pool & pond with kayaks

2.5 star property
Oak Bluffs
Beautiful Estate with salt water pool & pond with kayaks

The Club at New Seabury

3.5 star property
Mashpee
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.
$147 nightly
The price is $168
Dec 2 - Dec 3
Total with taxes and fees
The Club at New Seabury

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.
$781 nightly
The price is $893
Dec 8 - Dec 9
Total with taxes and fees
Coastal chic meets French Provençal in this newly renovated oceanfront home.

Sea Mist Resort

3.0 star property
Mashpee
8.6 out of 10, Excellent, (143)
"Overall was a wonderful stay. Unit could use a hair dryer."
United States
Susan
Sea Mist Resort

InnSeason Resorts Captain's Quarters

3.5 star property
Falmouth Heights
9.8 out of 10, Exceptional, (192)
"Great property! Would definitely stay again."
United States
Brad
InnSeason Resorts Captain's Quarters

Beachside Village Resort

3.0 star property
Falmouth
9.4 out of 10, Exceptional, (101)
"Very clean and quiet place to relax. Very friendly and professional! We will come back!"
United States
Emmanuelle Loriot
Beachside Village Resort

Newly Renovated Near Amazing Sunset Beach

Falmouth
9.8 out of 10, Exceptional, (73)
"Great stay"
United States
Michael S.
Newly Renovated Near Amazing Sunset Beach

Steps to the Ocean! Perfect Location!!!

Barnstable
10.0 out of 10, Exceptional, (234)
"I absolutely loved my stay at this charming cottage in Hyannis! The place was cozy, spotless, and beautifully maintained. A perfect mix of comfort and Cape Cod charm. The location was great, close to the beach and local shops, yet quiet enough to relax and unwind."
United States
Maria
Steps to the Ocean! Perfect Location!!!

Ocean Views From Every Room, Beach 30 Seconds Away!

West Hyannisport
10.0 out of 10, Exceptional, (112)
"The house was perfect for our family gathering. We did not lack for anything. The owners were very responsive. The view is fantastic and we enjoyed the beach. "
United States
Anthony F.
Ocean Views From Every Room, Beach 30 Seconds Away!

Sleeps 12, amazing view, tennis court, basketball court, beaches

Edgartown
9.6 out of 10, Exceptional, (40)
"Great family friendly home with lots of living space and activities such as tennis, pickle ball, ping pong, and games all on the property. My family of 10, inclusive of 4 grandchildren had an awesome time."
United States
Bob B.
Sleeps 12, amazing view, tennis court, basketball court, beaches

New, dog-friendly 5-bed home. Steps to Keyes Beach, Main Street, and Harbor!

Barnstable
10.0 out of 10, Exceptional, (151)
"Great house - extra clean and great location"
United States
Matt S.
New, dog-friendly 5-bed home. Steps to Keyes Beach, Main Street, and Harbor!

Unique oceanfront windmill with breathtaking views of Nantucket Sound.

West Hyannisport
10.0 out of 10, Exceptional, (92)
"Had an amazing stay—such an amazing location and beautiful property! Deborah was also extremely responsive the entire stay, quickly answering any questions that I had and giving great recommendations of good restaurants/things to do in the area!"
United States
Danyon H.
Unique oceanfront windmill with breathtaking views of Nantucket Sound.

Oceanside Cottage condo next to beach 2bedroom 1bath for 4-6 people

Barnstable
8.8 out of 10, Excellent, (28)
"It was very comfortable with upgraded kitchen and bathroom. It had all we needed. The owner was very responsive . Easy check in process. The location was perfect, just across from a beautiful ocean beach and very near Hyannis and many attractions. "
United States
Helene M.
Oceanside Cottage condo next to beach 2bedroom 1bath for 4-6 people

Steps to the beach with an ocean view,

Barnstable
10.0 out of 10, Exceptional, (139)
"We enjoyed our stay so close to the beach enormously. The location is great for exploring Cape Cod as it’s so central."
United States
Robert M.
Steps to the beach with an ocean view,
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 $168 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?

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs: Visitors give good reviews to this Oak Bluffs vacation home rental, which is located in the city center and has a patio, a garden, and a barbecue grill 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 vacation rentals will I find in Oak Bluffs?

Choose from 259 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 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 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.