Oak Bluffs Vacation Rentals

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Check prices for these dates

Tonight
Dec 25 - Dec 26
Tomorrow
Dec 26 - Dec 27
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Oak Bluffs vacation rentals

TV, fireplace, books
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

Vacation Home in Oak Bluffs

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
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 26 - Dec 27
Total with taxes and fees
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Smart TV
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

Apartment in Oak Bluffs

Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
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 26 - Dec 27
Total with taxes and fees
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
Interior
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Vacation Home in Oak Bluffs

MOST CHIC SPOT! Your Martha's Vineyard Getaway!
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.
$1,085 nightly
The price is $1,212
Dec 26 - Dec 27
Total with taxes and fees
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Interior
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

Apartment in Oak Bluffs

Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
9.4 out of 10, Exceptional, (91)
"Great place to stay in Oak Bluffs"
United States
Stephen S.
$446 nightly
The price is $498
Dec 26 - Dec 27
Total with taxes and fees
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Private beach nearby, beach bar
The Club at New Seabury

Condo resort in New Seabury

The Club at New Seabury
3.5 star property
9.0 out of 10, Wonderful, (341)
"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 $169
Dec 28 - Dec 29
Total with taxes and fees
The Club at New Seabury
On the beach, white sand
InnSeason Resorts Captain's Quarters

Aparthotel in Falmouth Heights

InnSeason Resorts Captain's Quarters
3.5 star property
9.8 out of 10, Exceptional, (192)
"Great property! Would definitely stay again."
United States
Brad
$117 nightly
The price is $134
Jan 1 - Jan 2, 2026
Total with taxes and fees
InnSeason Resorts Captain's Quarters
Exterior
The SandDollar Suite - Private Deck with Gorgeous Views of Onset Beach

Apartment in Onset

The SandDollar Suite - Private Deck with Gorgeous Views of Onset Beach
9.4 out of 10, Exceptional, (9)
"Great location"
United States
Robert C.
$345 nightly
The price is $385
Dec 26 - Dec 27
Total with taxes and fees
The SandDollar Suite - Private Deck with Gorgeous Views of Onset Beach
Exterior
Amazing Onset Getaway in the Starfish Suite

Condo in Onset

Amazing Onset Getaway in the Starfish Suite
9.8 out of 10, Exceptional, (24)
"Location was unbelievable-right next to beach"
United States
Terry B.
$379 nightly
The price is $423
Dec 26 - Dec 27
Total with taxes and fees
Amazing Onset Getaway in the Starfish Suite
Exterior
The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!

Apartment in Onset

The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!
9.8 out of 10, Exceptional, (28)
"The space was perfect for our needs. The beds were comfortable, the rooms were very clean. If needed, we would definitely come back to this rental."
United States
Lynn
$345 nightly
The price is $385
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!
Beach
Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area

Vacation Home in Falmouth

Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area
10.0 out of 10, Exceptional, (8)
"A beautiful home conveniently located-very clean Nd comfortable for 6 long time friends."
United States
Linda W.
$497 nightly
The price is $569
Jan 16 - Jan 17, 2026
Total with taxes and fees
Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area
Exterior
Spacious and Bright , Very Close to Beach!

Apartment in Onset

Spacious and Bright , Very Close to Beach!
9.6 out of 10, Exceptional, (22)
"Amazing location, clean, spacious suite, great communication with the host, overall a great experience! "
United States
Bernadette C.
$345 nightly
The price is $385
Jan 1 - Jan 2, 2026
Total with taxes and fees
Spacious and Bright , Very Close to Beach!
Terrace/patio
Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC

Vacation Home in Barnstable

Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC
10.0 out of 10, Exceptional, (4)
"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.
$583 nightly
The price is $667
Dec 26 - Dec 27
Total with taxes and fees
Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC
5 bedrooms, desk, iron/ironing board, travel crib
Coastal chic meets French Provençal in this newly renovated oceanfront home.

Vacation Home in East Falmouth

Coastal chic meets French Provençal in this newly renovated oceanfront home.
10.0 out of 10, Exceptional, (88)
"This is an excellent home well-kept great location, and the Host is easy to communicate with. "
United States
Gary B.
$781 nightly
The price is $893
Jan 3 - Jan 4, 2026
Total with taxes and fees
Coastal chic meets French Provençal in this newly renovated oceanfront home.
Indoor pool, outdoor pool, sun loungers
Sea Mist Resort

Aparthotel in Mashpee

Sea Mist Resort
3.0 star property
8.6 out of 10, Excellent, (144)
"Just there for one night but very enjoyable stay."
United States
Shawna
$137 nightly
The price is $157
Dec 29 - Dec 30
Total with taxes and fees
Sea Mist Resort
Exterior
Welcome to the Cape! Cute, quiet and clean apartment ready for your stay.

Apartment in Bourne

Welcome to the Cape! Cute, quiet and clean apartment ready for your stay.
10.0 out of 10, Exceptional, (21)
"This is a wonderful place to stay with the amenities of home. Spacious, private, with lots of places nearby to see and explore."
United States
Becky P.
$186 nightly
The price is $213
Dec 29 - Dec 30
Total with taxes and fees
Welcome to the Cape! Cute, quiet and clean apartment ready for your stay.
Terrace/patio
The Seashell Cove - Martha's Vineyard

Vacation Home in Katama

The Seashell Cove - Martha's Vineyard
9.8 out of 10, Exceptional, (24)
"Property was perfectly kept and very comfortable. "
United States
Steve D.
$514 nightly
The price is $574
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Seashell Cove - Martha's Vineyard
Fridge, microwave, oven, stovetop
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Vacation Home in Falmouth

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
10.0 out of 10, Exceptional, (211)
"Nicely furnished and very comfortable. Very private, yet convenient location. "
United States
John H.
$432 nightly
The price is $494
Jan 4 - Jan 5, 2026
Total with taxes and fees
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Outdoor dining
Newly Renovated Martha's Vineyard Vacation Rental!

Vacation Home in Katama

Newly Renovated Martha's Vineyard Vacation Rental!
9.6 out of 10, Exceptional, (47)
"We really enjoyed our stay. The house was conveniently located near Edgartown and South Beach in a quiet neighborhood. The house had everything we needed and more and was in great shape. Would definitely stay here again. "
United States
Patrick S.
$558 nightly
The price is $623
Dec 30 - Dec 31
Total with taxes and fees
Newly Renovated Martha's Vineyard Vacation Rental!
Exterior
Falmouth Oasis

Vacation Home in Falmouth

Falmouth Oasis
2.0 star property
$380 nightly
The price is $435
Dec 30 - Dec 31
Total with taxes and fees
Falmouth Oasis
Outdoor pool, a heated pool
Cozy efficiency apartment/heated pool

Apartment in Chilmark

Cozy efficiency apartment/heated pool
9.6 out of 10, Exceptional, (21)
"We loved this property and would love to return!"
United States
Clifford L.
$378 nightly
The price is $422
Dec 31 - Jan 1, 2026
Total with taxes and fees
Cozy efficiency apartment/heated pool
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

Hampton Inn Cape Cod Canal

Hampton Inn Cape Cod Canal

10/10 Excellent
"Very nicely decorated for the holidays. "
Bernadette 1-night trip
Posted 4 days ago
Hampton Inn Cape Cod Canal

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 $134 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.

Explore a world of travel with Expedia

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?

Oak Bluffs Town Beach and Inkwell 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.