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

6.4 out of 10, (31)
"The weather was perfect and our crew made the best of our trip."
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

9.4 out of 10, Exceptional, (88)
"The location of this property cannot be beat! Our second time staying here."
The price is €468
includes taxes & fees
1 Nov - 2 Nov
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

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

9.4 out of 10, Exceptional, (91)
"Close to buses, restaurants and ferries. 10/10, we would stay again."
The price is €440
includes taxes & fees
12 Oct - 13 Oct
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

Spacious colonial home close to town with AC, porches, & W/D

10.0 out of 10, Exceptional, (5)
"We had such a great stay here. Very clean and super close to town. We would definitely stay here again. Thanks!"
Spacious colonial home close to town with AC, porches, & W/D

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."
The price is €1,070
includes taxes & fees
12 Oct - 13 Oct
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

9.0 out of 10, Wonderful, (2)
"The house was lovely. Very clean and orderly. Beautiful back porch that we enjoyed very much. The beds were very comfortable. Our only complaint was the Master bathroom needs some updating. The shower head desperately needs to be changed and the lighting is extremely poor. Also, only 1 half size mirror on the whole first floor. Other than that, it was perfect."
The price is €592
includes taxes & fees
24 Oct - 25 Oct
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

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

6.8 out of 10, (23)
"The furniture and amenities provided were good"
Cozy getaway in a central location w/ a full kitchen & furnished deck

Retreat to Martha's Vineyard with a Private Pool & Outdoor Living in Oak Bluffs

10.0 out of 10, Exceptional, (7)
"Excellent property with a wonderful pool and quiet neighborhood. Listing was accurate as described and communication with owner was prompt and helpful to all questions. Excellent amenities including game room with pool table and boats games. Great location for adults and children to enjoy. "
Retreat to Martha's Vineyard with a Private Pool & Outdoor Living in Oak Bluffs

Quaint, ranch style home in Oak Bluffs with central air

2.0 star property
9.4 out of 10, Exceptional, (3)
"Exactly as expected. Very clean and was nice and cool upon arrival. Well stocked and had everything we needed for our stay, including towels, linens, toiletries, and cleaning supplies. Very quick responses from property management. Phenomenal location. Perfect for anyone looking for a solid, clean and comfortable camp on the island. "
Quaint, ranch style home in Oak Bluffs with central air

Updated house close to town and beach with patio, AC, and games

2.0 star property
9.6 out of 10, Exceptional, (5)
"Great location, walking distance to beach, restaurants and shops!"
Updated house close to town and beach with patio, AC, and games

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (336)
"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 "
The Club at New Seabury

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (186)
"Great location and helpful staff"
InnSeason Resorts Captain's Quarters

Coastal chic meets French Provençal in this newly renovated oceanfront home.

10.0 out of 10, Exceptional, (86)
"Great stay! "
The price is €1,182
includes taxes & fees
27 Oct - 28 Oct
Coastal chic meets French Provençal in this newly renovated oceanfront home.

Sea Mist Resort

3.0 star property
8.6 out of 10, Excellent, (137)
"Just there for one night but very enjoyable stay."
The price is €173
includes taxes & fees
7 Nov - 8 Nov
Sea Mist Resort

Steps to the beach with an ocean view,

10.0 out of 10, Exceptional, (133)
"Great stay."
Steps to the beach with an ocean view,

Steps to the Ocean! Perfect Location!!!

10.0 out of 10, Exceptional, (227)
"Perfect for a couple and two kids"
Steps to the Ocean! Perfect Location!!!

Beach front, fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub

10.0 out of 10, Exceptional, (112)
"The location and amenities were perfect. We are looking forward to returning next year."
Beach front, fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub

Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly

10.0 out of 10, Exceptional, (64)
"The house was well stocked and had everything you could need. "
Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly

By the Water - Steps to the Beach - 4Br, AC, Views of Vineyard Sound

9.8 out of 10, Exceptional, (23)
"We had a great week staying at this property. It's well maintained and had plenty of room for a family getaway to the Cape. Steps away from the beach, this property is well taken care of and had everything we needed for a comfortable stay. This would be our first choice for any future trips to the Cape."
By the Water - Steps to the Beach - 4Br, AC, Views of Vineyard Sound

New Coastal House, Steps to Keyes Beach, Main Street, Harbor; AC, Linens, Wi-Fi

9.8 out of 10, Exceptional, (161)
"Alex' house was perfect for us. The fenced in yard was great for our dog and the location is top notch. We could load up the beach wagon and take the short walk to the beach. Alex was extremely accommodating with several recommendations for us."
New Coastal House, Steps to Keyes Beach, Main Street, Harbor; AC, Linens, Wi-Fi
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 €173 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. Other favourite homes for rent in Oak Bluffs are MOST CHIC SPOT! Your Martha's Vineyard Getaway! and Cozy getaway in a central location w/ a full kitchen & furnished deck.

How many holiday rentals will I find in Oak Bluffs?

Choose from 257 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 Flying Horses Carousel.

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.