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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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, (96 reviews)
"Memorial Day weekend on the Vineyard was perfect."
United States
Cassandra
The price is SAR 1,126
SAR 1,887 total
includes taxes & fees
4 Oct - 5 Oct
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
An outdoor seating area with Adirondack chairs and a table, surrounded by trees.

2. 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 SAR 1,235
SAR 2,223 total
includes taxes & fees
30 Sep - 1 Oct
Walk to Beach & Lighthouse: Oak Bluffs Studio!
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 SAR 1,348
SAR 2,982 total
includes taxes & fees
8 Oct - 9 Oct
Oak Bluffs 4BR • 5 Min Drive to Downtown
A beach with a sandy shore and calm water.

4. Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town

Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town
Oak Bluffs
8.8 out of 10, Excellent, (9 reviews)
"Loved our little cottage"
United States
Linda T.
Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town
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, (9 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
The price is SAR 1,494
SAR 4,848 total
includes taxes & fees
8 Oct - 9 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
6.6 out of 10, (11 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 SAR 1,186
SAR 2,533 total
includes taxes & fees
30 Sep - 1 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 SAR 1,641
SAR 3,288 total
includes taxes & fees
9 Oct - 10 Oct
< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs
A modern kitchen with white cabinets, a central island with blue drawers, and stainless steel appliances.

8. Brand New Guest house

Brand New Guest house
Oak Bluffs
10.0 out of 10, Exceptional, (7 reviews)
"This is a new, beautiful and tastefully decorated 2 bedroom one bathroom house with a really nice big yard. Owner was very responsive and We had everything we needed for an enjoyable stay!"
United States
Elizabeth O.
The price is SAR 1,352
SAR 4,206 total
includes taxes & fees
1 Oct - 2 Oct
Brand New Guest house
A room with a view of the sea through large windows, a wooden deck, and a pier with structures.

9. 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 SAR 1,014
SAR 1,753 total
includes taxes & fees
1 Oct - 2 Oct
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
A spacious living area with a high ceiling, a dining table, and a kitchen area.

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

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.6 out of 10, Exceptional, (9 reviews)
"The host was very responsive.We definitely recommend this house as family friendly."
United States
Karen M.
The price is SAR 1,858
SAR 3,837 total
includes taxes & fees
4 Oct - 5 Oct
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
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 SAR 5,069
SAR 7,842 total
includes taxes & fees
8 Oct - 9 Oct
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
A two-story house with a stone facade, a covered patio, and a well-maintained garden.

12. 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 SAR 9,386
SAR 13,244 total
includes taxes & fees
12 Oct - 13 Oct
Beautiful Estate with salt water pool & pond with kayaks
An outdoor seating area with Adirondack chairs and a table, surrounded by trees.

13. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is SAR 1,461
SAR 3,384 total
includes taxes & fees
8 Oct - 9 Oct
Walk to Beach! Oak Bluffs Home & Studio
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 SAR 1,089
SAR 1,858 total
includes taxes & fees
12 Oct - 13 Oct
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 SAR 807
SAR 923 total
includes taxes & fees
30 Sep - 1 Oct
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, (90 reviews)
"Great condo, great location. Fully equipped kitchen and awesome patio. "
United States
Jeff V.
The price is SAR 331
SAR 1,152 total
includes taxes & fees
8 Oct - 9 Oct
New Seabury Cape Condo + Pool & Beach Escape
A deck with a fire pit, outdoor seating, and a blue umbrella.

17. 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 SAR 719
SAR 2,692 total
includes taxes & fees
30 Sep - 1 Oct
Cozy Cottage walk to Menauhant Beach
A high-ceiling room with skylights, a sofa, chairs, a coffee table, and a radiator.

18. Charming 3 Bedroom Apartment . Walk to Ferry, Shops & Beach

Charming 3 Bedroom Apartment . Walk to Ferry, Shops & Beach
Tisbury
The price is SAR 1,498
SAR 3,594 total
includes taxes & fees
11 Oct - 12 Oct
Charming 3 Bedroom Apartment . Walk to Ferry, Shops & 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 SAR 657
SAR 1,616 total
includes taxes & fees
1 Oct - 2 Oct
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!
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

Iris Hotel Cape Cod

Iris Hotel Cape Cod

10/10 Excellent
"Verry good hotel, the breakfast is perfect."
Matheus 1-night trip
Posted less than an hour ago
Iris Hotel Cape Cod

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.