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

Oak Bluffs Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Oak Bluffs vacation rentals

An outdoor seating area with Adirondack chairs and a table, surrounded by trees.

1. 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 AED 566
AED 1,407 total
includes taxes & fees
8 Nov - 9 Nov
Walk to Beach & Lighthouse: Oak Bluffs Studio!
A room with a view of the sea through large windows, a wooden deck, and a pier with structures.

2. 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)
"Great location. Clear instructions"
United States
Sherise M.
The price is AED 992
AED 1,735 total
includes taxes & fees
5 Nov - 6 Nov
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Room

3. 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 AED 507
AED 1,038 total
includes taxes & fees
11 Nov - 12 Nov
Sunlit Studio Retreat with Incredible Outdoor Deck on Martha’s Vineyard
A modern kitchen with a large island, a dining area with a table and chairs, and a view of a green garden through large windows.

4. Vineyard Luxury "Yurt"

Vineyard Luxury "Yurt"
Oak Bluffs
10.0 out of 10, Exceptional, (1 review)
"The yurt was clean and nice and served all of our needs."
United States
David C.
The price is AED 834
AED 1,637 total
includes taxes & fees
11 Nov - 12 Nov
Vineyard Luxury "Yurt"
A modern kitchen with stainless steel appliances, a dining area with a wooden table set for six, and a living area with a sofa and TV.

5. 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 AED 988
AED 2,536 total
includes taxes & fees
11 Nov - 12 Nov
Oak Bluffs 4BR • 5 Min Drive to Downtown
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 AED 966
AED 2,261 total
includes taxes & fees
5 Nov - 6 Nov
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 AED 1,605
AED 3,278 total
includes taxes & fees
5 Nov - 6 Nov
< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs
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.

8. 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, (99 reviews)
"Memorial Day weekend on the Vineyard was perfect."
United States
Cassandra
The price is AED 992
AED 1,735 total
includes taxes & fees
5 Nov - 6 Nov
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
A two-story house with a stone facade, a covered patio, and a well-maintained garden.

9. Beautiful Estate with salt water pool & pond with kayaks

Beautiful Estate with salt water pool & pond with kayaks
Oak Bluffs
10.0 out of 10, Exceptional, (3 reviews)
"Brenda and Derek were amazing hosts. They have a beautifully landscaped property with all the amenities needed for a relaxing family vacation. They are super responsive and take a lot of pride in giving their guests a top-notch experience. We will definitely consider staying at their properties again."
United States
Lamar A.
The price is AED 7,346
AED 11,131 total
includes taxes & fees
30 Nov - 1 Dec
Beautiful Estate with salt water pool & pond with kayaks
An outdoor seating area with Adirondack chairs and a table, surrounded by trees.

10. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is AED 1,142
AED 3,003 total
includes taxes & fees
5 Nov - 6 Nov
Walk to Beach! Oak Bluffs Home & Studio
A coastal hotel with multiple beachside rooms, a large covered area, and a beach with umbrellas.

11. 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 AED 541
AED 619 total
includes taxes & fees
5 Nov - 6 Nov
The Club at New Seabury
A wooden deck with wicker chairs and a round table with a sun design.

12. 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)
"Cute, Cozy, comfortable, clean and quiet small apartment with full kitchen, a comfortable king bed with views of the lake from the kitchen/living room area and bedroom. It also had a nice spot outside on a deck with two chairs and table where we read, and watched the boats go by! Our host Stephen was very nice and helpful he responded quickly to our texts! The apt is near the bus route which is fabulous on the vineyard it goes to all the major spots you’d want to go! And it’s free!! It is also...
United States
Liz C.
The price is AED 1,074
AED 1,840 total
includes taxes & fees
10 Nov - 11 Nov
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
A patio with wicker chairs and a small table, a grassy yard, a wooden fence, and a view of a body of water.

13. 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 AED 579
AED 1,591 total
includes taxes & fees
5 Nov - 6 Nov
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!
A modern kitchen with white cabinetry, a dining area with a wooden table and white chairs, and a large window providing natural light.

14. 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 AED 2,196
AED 6,121 total
includes taxes & fees
15 Nov - 16 Nov
New 4 BR house near center and beaches with bikes
Exterior

15. 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 AED 664
AED 2,164 total
includes taxes & fees
5 Nov - 6 Nov
Charming Guesthouse | Walk to Beach | Downtown
A spacious kitchen with a central island, stainless steel appliances, and a dining area with a rug and chairs.

16. Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Falmouth
10.0 out of 10, Exceptional, (227 reviews)
"Great location "
United States
Stephanie B.
The price is AED 661
AED 1,921 total
includes taxes & fees
5 Nov - 6 Nov
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
A bedroom with a bed, a dresser, a sofa, and a painting on the wall.

17. Charming studio in tranquil Falmouth with AC

Charming studio in tranquil Falmouth with AC
Falmouth
10.0 out of 10, Exceptional, (4 reviews)
"Very clean and comfy place, a short drive to Falmouth center! Communication was very easy and check-in simple."
United States
Harry H.
The price is AED 595
AED 849 total
includes taxes & fees
5 Nov - 6 Nov
Charming studio in tranquil Falmouth with AC
A covered outdoor seating area with a view of the ocean, a ceiling fan, and a flat-screen TV on the wall.

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

Coastal chic meets French Provençal in this newly renovated oceanfront home.
East Falmouth
10.0 out of 10, Exceptional, (101 reviews)
"Great views, beautiful setting . Scott was so attentive and easy to work with. We had a great time!"
United States
Ben L.
The price is AED 1,468
AED 3,803 total
includes taxes & fees
19 Nov - 20 Nov
Coastal chic meets French Provençal in this newly renovated oceanfront home.
A spacious living area with wooden beams, a dining table, and a sofa.

19. The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard
Katama
9.8 out of 10, Exceptional, (31 reviews)
"Nice and clean house, good location on the island, nice neighborhood "
United States
Eric C.
The price is AED 2,479
AED 3,898 total
includes taxes & fees
8 Nov - 9 Nov
The Seashell Cove - Martha's Vineyard
A modern kitchen with a large window overlooking a lake, a dining area with chairs, and a living room with a sofa.

20. WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy

WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy
Sandwich
10.0 out of 10, Exceptional, (4 reviews)
"We really enjoyed our stay at this property. The view was amazing and had our own private beach to lounge at!"
United States
Sean H.
The price is AED 551
AED 1,358 total
includes taxes & fees
5 Nov - 6 Nov
WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Oak Bluffs Hotel Reviews

The Coonamessett

The Coonamessett

10/10 Excellent
"Very beautiful hotel, perfect for a long stay and enjoy the town"
Sergio Rodrigo 3-night trip
Posted 2 days ago
The Coonamessett

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?

Coastal Retreat | Walk to Inkwell Beach, Dining & Flying Horses Carousel: Visitors give good reviews to this Oak Bluffs vacation home rental, which is located near the beach and has a balcony, a garden, and a barbecue grill 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 you can cook with friends or family. Other favorite 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 vacation rentals will I find in Oak Bluffs?

Choose from 270 Expedia vacation rentals in Oak Bluffs for a memorable vacation.

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 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.