Oak Bluffs Holiday Rentals

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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
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
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 AU$1,880
includes taxes & fees
15 Oct - 16 Oct
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
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 AU$773
includes taxes & fees
15 Oct - 16 Oct
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2026!
10.0 out of 10, Exceptional, (71)
"Large home with plenty of room for extended family. Located in quiet neighborhood close to Oak Bluffs, would highly recommend."
Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2026!
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
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
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 AU$1,040
includes taxes & fees
21 Oct - 22 Oct
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
The quintessential MV home. Now booking for 2026!
9.8 out of 10, Exceptional, (55)
"Just a quick 4 minute drive to downtown. Listing was accurate and place was clean!"
The quintessential MV home. Now booking for 2026!
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
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard
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."
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard
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, (187)
"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, (87)
"Great stay! "
The price is AU$1,941
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, (138)
"Just there for one night but very enjoyable stay."
The price is AU$274
includes taxes & fees
7 Nov - 8 Nov
Sea Mist Resort
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!!!
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,
Beachside Village Resort
3.0 star property
9.2 out of 10, Wonderful, (99)
"Great location! Nice property! "
Beachside Village Resort
Newly Renovated Near Amazing Sunset Beach
9.8 out of 10, Exceptional, (70)
"Amazing property for any trip to North Falmouth. We absolutely loved the location, outdoor shower, layout, and decks. Bill was incredibly responsive and an excellent host. "
Newly Renovated Near Amazing Sunset Beach
Gorgeous Cottage steps from the beach
8.4 out of 10, Very good, (24)
"Location to town & beach was great. Cottage was listed accurate online. Communication with owner was welcoming. The cottage was a nice weekend get away."
Gorgeous Cottage steps from the beach
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, 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 favourite 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 depend 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 AU$274 per night. Entering your travel dates in the search wizard might find you 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.