A row of colorful, historic houses with a central path.

Oak Bluffs Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Oak Bluffs holiday rentals

A living room with a flat-screen TV on a stand, a black leather chair, and a sofa. There are two windows with curtains, one of which offers a view of the sea.

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

Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
Oak Bluffs
9.4 out of 10, Exceptional, (98 reviews)
"Memorial Day weekend on the Vineyard was perfect."
United States
Cassandra
The price is AU$686
includes taxes & fees
22 Oct - 23 Oct
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
Room

2. Sunlit Studio Retreat with Incredible Outdoor Deck on Martha’s Vineyard

Sunlit Studio Retreat with Incredible Outdoor Deck on Martha’s Vineyard
Oak Bluffs
The price is AU$389
includes taxes & fees
22 Oct - 23 Oct
Sunlit Studio Retreat with Incredible Outdoor Deck on Martha’s Vineyard
A rocky beach with clear water, a sandy shore, and a hilly landscape in the background.

3. Oak Bluffs 4BR • 5 Min Drive to Downtown

Oak Bluffs 4BR • 5 Min Drive to Downtown
Oak Bluffs
10.0 out of 10, Exceptional, (1 review)
"This place was just what we needed! Would definitely stay again. Cozy and feels very homey! Thanks!"
United States
Chris S.
The price is AU$1,055
includes taxes & fees
15 Nov - 16 Nov
Oak Bluffs 4BR • 5 Min Drive to Downtown
An outdoor seating area with Adirondack chairs and a table, surrounded by trees.

4. Walk to Beach & Lighthouse: Oak Bluffs Studio!

Walk to Beach & Lighthouse: Oak Bluffs Studio!
Oak Bluffs
7.6 out of 10, Good, (14 reviews)
"The unit was clean and sufficient for 2 people. Outside could use some attention."
United States
Donna R.
The price is AU$866
includes taxes & fees
22 Oct - 23 Oct
Walk to Beach & Lighthouse: Oak Bluffs Studio!
A single-story house with a covered porch, a hammock, and a brick pathway leading to the front door.

5. Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
Oak Bluffs
9.8 out of 10, Exceptional, (10 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
The price is AU$1,839
includes taxes & fees
23 Oct - 24 Oct
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
A circular stone patio with Adirondack chairs and a small table in a forested area.

6. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Oak Bluffs
7.0 out of 10, Good, (12 reviews)
"Loved this spot. Perfect central island location. Fantastic owner with an incredible response time. Would recommend this property to all5 stars"
United States
Eli R.
The price is AU$1,019
includes taxes & fees
25 Oct - 26 Oct
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
A spacious living room with a wooden staircase, a fireplace, and a leather sofa.

7. < 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs
Oak Bluffs
7.4 out of 10, Good, (3 reviews)
"House was neat architectural wise and family history of home ownership was very cool. However, listing noted there was a washer/dryer and there was not. House also noted that there was a fire pit and it was rusted through. Screen door handles were broken, windows need repair, and house has animals living in the downstairs bathroom wall. House needs updates to charge what was being charged a night. In addition, there was a Nor’easter that hit the island and we attempted to contact the host to let...
United States
Kate K.
The price is AU$1,284
includes taxes & fees
1 Nov - 2 Nov
< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs
A bedroom with a large bed, a bedside table, a lamp, and a window with curtains.

8. Delightful 3-bedroom house with AC in Oak Bluffs

Delightful 3-bedroom house with AC in Oak Bluffs
Oak Bluffs
The price is AU$1,605
includes taxes & fees
30 Oct - 31 Oct
Delightful 3-bedroom house with AC in Oak Bluffs
A spacious living area with a high ceiling, a dining table, and a kitchen area.

9. A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.8 out of 10, Exceptional, (11 reviews)
"A clean accommodating space with an accommodating host - I recommended!"
United States
Collins E.
The price is AU$1,510
includes taxes & fees
25 Oct - 26 Oct
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
A room with a view of the sea through large windows, a wooden deck, and a pier with structures.

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

Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Oak Bluffs
9.4 out of 10, Exceptional, (98 reviews)
"Danny was a great host. Unit clean. Walking distance to everything"
United States
Alvin
The price is AU$686
includes taxes & fees
23 Oct - 24 Oct
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
A modern interior with a wooden staircase, a kitchen area, and a living space with a sofa and coffee table.

11. MOST CHIC SPOT! Your Martha's Vineyard Getaway!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Oak Bluffs
9.8 out of 10, Exceptional, (12 reviews)
"This was an excellent stay at a beautiful property in Oak Bluffs! Rebecca was a great host who provided clear instructions and helped answer questions in a timely manner. Rooms were spacious, most tastefully decorated and we had everything that we needed. I definitely recommend staying here to have an unparalleled experience of the Vineyard."
United States
Priyanka D.
The price is AU$3,091
includes taxes & fees
1 Nov - 2 Nov
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
An outdoor seating area with Adirondack chairs and a table, surrounded by trees.

12. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is AU$1,167
includes taxes & fees
4 Nov - 5 Nov
Walk to Beach! Oak Bluffs Home & Studio
A modern kitchen with a marble countertop, a central island, and a hanging light fixture.

13. Brand new! Lovely apartment-Vineyard Haven

Brand new! Lovely apartment-Vineyard Haven
Tisbury
10.0 out of 10, Exceptional, (34 reviews)
"Fabulous property! Clean and very comfy."
United States
Claudia
The price is AU$747
includes taxes & fees
22 Oct - 23 Oct
Brand new! Lovely apartment-Vineyard Haven
A view through a window with a wooden frame, overlooking a garden with various plants and a body of water in the background.

14. Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.

Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
Tisbury
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful view of the lagoon; ideal place for a couple or single. Leisurely walk to town and close to public transportation."
United States
Adrienne W.
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
A coastal hotel with multiple beachside rooms, a large covered area, and a beach with umbrellas.

15. The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (371 reviews)
"The New Seabury resort is beautiful & has excellent customer service. The 4/5 stars is because the unit we stayed in needs some updating. However, the layout, cleanliness, & location is good."
United States
Kathleen
The price is AU$283
includes taxes & fees
15 Nov - 16 Nov
The Club at New Seabury
A residential area with a well-maintained lawn, a stone retaining wall, and a two-story house with a blue door.

16. New 4 BR house near center and beaches with bikes

New 4 BR house near center and beaches with bikes
Katama
9.8 out of 10, Exceptional, (13 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
The price is AU$2,401
includes taxes & fees
15 Nov - 16 Nov
New 4 BR house near center and beaches with bikes
A boat docked at a concrete pier with a sandy shore in the background.

17. Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!
Seconsett Island
10.0 out of 10, Exceptional, (45 reviews)
"Great place with kayaks and paddle boards, beach, close to Mashpee Commons. Host was great and place was clean and quaint."
United States
Michele M.
The price is AU$606
includes taxes & fees
22 Oct - 23 Oct
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!
A table set for dining with a view of the ocean, surrounded by wicker chairs, under a covered patio.

18. Water Views, Walk to Fairmount Heights Beach

Water Views, Walk to Fairmount Heights Beach
Falmouth Heights
10.0 out of 10, Exceptional, (2 reviews)
Water Views, Walk to Fairmount Heights Beach
A modern living room with a grey sofa, a coffee table, and a fireplace.

19. LUX on Main | Downtown | Parking | Sleeps 6, #203

LUX on Main | Downtown | Parking | Sleeps 6, #203
Falmouth
10.0 out of 10, Exceptional, (6 reviews)
"Nice vacation spot in a great location host was excellent and the apartment was well stocked with everything you need! Very nice stay!"
United States
Jen M.
The price is AU$1,127
includes taxes & fees
22 Oct - 23 Oct
LUX on Main | Downtown | Parking | Sleeps 6, #203
Exterior

20. Charming Guesthouse | Walk to Beach | Downtown

Charming Guesthouse | Walk to Beach | Downtown
Falmouth
10.0 out of 10, Exceptional, (1 review)
"The house was very convenient to the beach, Aldi’s, Walmart, and local restaurants & shops. I wasn’t sure how private it was being a guest house, but I never felt that we didn’t have privacy. Our dogs enjoyed the little fenced in yard. We appreciated the updated bathroom and kitchen. The weather was so pleasant a small outdoor area would have been nice, and we missed not having a washer & dryer and dishwasher, but overall it was clean and cozy. We would stay there again! We loved the Cape,...
United States
Kandy W.
The price is AU$886
includes taxes & fees
22 Oct - 23 Oct
Charming Guesthouse | Walk to Beach | Downtown
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

Summercamp

Summercamp

10/10 Excellent
"Loved the location. Staff were so friendly. Neat and clean property."
Maria 3-night trip
Posted 2 days ago
Summercamp

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$283 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?

Coastal Retreat | Walk to Inkwell Beach, Dining & Flying Horses Carousel: This highly rated holiday home rental in Oak Bluffs is located near the beach, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Other favourite homes for rent in Oak Bluffs are Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs and Quaint, ranch style home in Oak Bluffs with central air.

How many holiday rentals will I find in Oak Bluffs?

Choose from 270 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 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 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.