Holiday Rentals in Oak Bluffs

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Holiday 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.
The price is €1,046
includes taxes & fees
2 Dec - 3 Dec
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Cozy getaway in a central location w/ a full kitchen & furnished deck

Oak Bluffs
6.6 out of 10, (25)
"The furniture and amenities provided were good"
United States
Joseph T.
Cozy getaway in a central location w/ a full kitchen & furnished deck

Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

Oak Bluffs
9.4 out of 10, Exceptional, (91)
"Awesome view"
United States
Dave B.
The price is €442
includes taxes & fees
1 Dec - 2 Dec
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

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!

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.
The price is €792
includes taxes & fees
9 Dec - 10 Dec
A NOSTALGIC SPACE! 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

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.
The price is €442
includes taxes & fees
27 Nov - 28 Nov
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

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.
The price is €145
includes taxes & fees
30 Nov - 1 Dec
The Club at New Seabury

Sea Mist Resort

3.0 star property
Mashpee
8.6 out of 10, Excellent, (142)
"Overall was a wonderful stay. Unit could use a hair dryer."
United States
Susan
Sea Mist Resort

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.
The price is €819
includes taxes & fees
8 Dec - 9 Dec
Coastal chic meets French Provençal in this newly renovated oceanfront home.

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!!!

Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome

West Tisbury
9.0 out of 10, Wonderful, (35)
"Great spot for a get away. Private with easy access to activities."
United States
Philip E.
Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome

Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown

Falmouth Heights
10.0 out of 10, Exceptional, (187)
"Great house with 4 bedrooms, good for couples. Walking distance to many places in Falmouth. Really enjoyed our stay here. Would stay again. "
United States
christine d.
Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown

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

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
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 €145 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. Another good choice for your trip to Oak Bluffs is MOST CHIC SPOT! Your Martha's Vineyard Getaway!.

How many holiday rentals will I find in Oak Bluffs?

Choose from 259 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 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 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.