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

Oak Bluffs Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Oak Bluffs vacation 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, (97 reviews)
"Memorial Day weekend on the Vineyard was perfect."
United States
Cassandra
The price is ￥47,355
￥84,633 total
includes taxes & fees
Oct 14 - Oct 15
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
A rocky beach with clear water, a sandy shore, and a hilly landscape in the background.

2. 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 ￥56,684
￥132,787 total
includes taxes & fees
Oct 8 - Oct 9
Oak Bluffs 4BR • 5 Min Drive to Downtown
An outdoor seating area with Adirondack chairs and a table, surrounded by trees.

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

Walk to Beach & Lighthouse: Oak Bluffs Studio!
Oak Bluffs
7.8 out of 10, Good, (12 reviews)
"The unit was clean and sufficient for 2 people. Outside could use some attention."
United States
Donna R.
The price is ￥51,933
￥98,915 total
includes taxes & fees
Oct 6 - Oct 7
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.

4. 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 ￥62,824
￥215,814 total
includes taxes & fees
Oct 6 - Oct 7
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.

5. 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 ￥49,881
￥112,844 total
includes taxes & fees
Oct 6 - Oct 7
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
A spacious living room with a wooden staircase, a fireplace, and a leather sofa.

6. < 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 ￥68,980
￥148,284 total
includes taxes & fees
Oct 9 - Oct 10
< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs
A spacious living area with a high ceiling, a dining table, and a kitchen area.

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

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.6 out of 10, Exceptional, (10 reviews)
"The host was very responsive.We definitely recommend this house as family friendly."
United States
Karen M.
The price is ￥78,136
￥170,148 total
includes taxes & fees
Oct 7 - Oct 8
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
A backyard with a seating area, a white fence, and a variety of plants.

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

Delightful 3-bedroom house with AC in Oak Bluffs
Oak Bluffs
The price is ￥70,748
￥180,585 total
includes taxes & fees
Oct 30 - Oct 31
Delightful 3-bedroom house with AC in Oak Bluffs
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 ￥394,625
￥598,072 total
includes taxes & fees
Oct 12 - Oct 13
Beautiful Estate with salt water pool & pond with kayaks
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 ￥42,620
￥78,638 total
includes taxes & fees
Oct 7 - Oct 8
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 ￥213,098
￥352,461 total
includes taxes & fees
Oct 6 - Oct 7
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 ￥61,404
￥147,402 total
includes taxes & fees
Oct 6 - Oct 7
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, (32 reviews)
"This property is quiet yet close enough to the business areas. Very clean, well maintained lovely unit with balcony. The host Joziane commutated with us from minutes after the booking to the end of stay, very helpful."
United States
Unspecified U.
The price is ￥36,227
￥77,494 total
includes taxes & fees
Oct 9 - Oct 10
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, (10 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.
The price is ￥45,777
￥82,693 total
includes taxes & fees
Oct 19 - Oct 20
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 ￥23,258
￥26,618 total
includes taxes & fees
Nov 1 - Nov 2
The Club at New Seabury
A modern living room with a sofa, chairs, a coffee table, and a dining area.

16. New Seabury Cape Condo + Pool & Beach Escape

New Seabury Cape Condo + Pool & Beach Escape
New Seabury
10.0 out of 10, Exceptional, (91 reviews)
"Great condo, great location. Fully equipped kitchen and awesome patio. "
United States
Jeff V.
The price is ￥13,908
￥50,603 total
includes taxes & fees
Oct 8 - Oct 9
New Seabury Cape Condo + Pool & Beach Escape
A residential area with a well-maintained lawn, a stone retaining wall, and a two-story house with a blue door.

17. 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, (12 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
The price is ￥83,661
￥263,067 total
includes taxes & fees
Oct 11 - Oct 12
New 4 BR house near center and beaches with bikes
A deck with a fire pit, outdoor seating, and a blue umbrella.

18. Cozy Cottage walk to Menauhant Beach

Cozy Cottage walk to Menauhant Beach
East Falmouth
8.8 out of 10, Excellent, (8 reviews)
"It was a great weekend spot. Had everything we needed, nicely decorated, and in a great and private location"
United States
Grace P.
The price is ￥37,109
￥128,460 total
includes taxes & fees
Oct 8 - Oct 9
Cozy Cottage walk to Menauhant Beach
A boat docked at a concrete pier with a sandy shore in the background.

19. 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, (44 reviews)
"Great stay!"
United States
Kian S.
The price is ￥27,624
￥71,904 total
includes taxes & fees
Oct 6 - Oct 7
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!
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 ￥30,994
￥101,051 total
includes taxes & fees
Oct 6 - Oct 7
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
"Thank you to Malika and the entire staff for wonderful customer service."
Dawn 3-night trip
Posted 1 hour ago
Summercamp

Find out more about Oak Bluffs

Search for holiday rentals in Oak Bluffs on Expedia! You can easily find your home rentals, villas, holiday apartments in Oak Bluffs using one of the methods below:

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Look no further and take a look at our great range of rental properties in Oak Bluffs!

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.