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

Oak Bluffs Vacation Rentals

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Our top choices for Oak Bluffs vacation rentals

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, (95 reviews)
"Memorial Day weekend on the Vineyard was perfect."
United States
Cassandra
The price is AED 1,102
AED 1,969 total
includes taxes & fees
20 Sep - 21 Sep
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

2. Beautiful Beachfront “Oasis by the Sea” in the Heart of Oak Bluffs!

Beautiful Beachfront “Oasis by the Sea” in the Heart of Oak Bluffs!
Oak Bluffs
10.0 out of 10, Exceptional, (61 reviews)
"We had the best girls weekend here! The space was perfect size for us. Great spaces for sitting and chatting, both inside and on the balcony. The location was perfect, right across from the ocean waves and shells on the beach. Walking distance to town and easy access to biking. It had everything we needed."
United States
Rachael C.
The price is AED 1,821
AED 3,380 total
includes taxes & fees
24 Sep - 25 Sep
Beautiful Beachfront “Oasis by the Sea” in the Heart of Oak Bluffs!

3. < 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 3,450 total
includes taxes & fees
17 Sep - 18 Sep
< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

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

Walk to Beach & Lighthouse: Oak Bluffs Studio!
Oak Bluffs
8.0 out of 10, Very good, (11 reviews)
"Very good experience Very clean owner very helpful My second time here"
United States
Diana
The price is AED 1,208
AED 2,302 total
includes taxes & fees
20 Sep - 21 Sep
Walk to Beach & Lighthouse: Oak Bluffs Studio!

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 AED 1,462
AED 4,796 total
includes taxes & fees
1 Oct - 2 Oct
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

6. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is AED 1,429
AED 3,430 total
includes taxes & fees
25 Sep - 26 Sep
Walk to Beach! Oak Bluffs Home & Studio

7. 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 AED 1,322
AED 3,360 total
includes taxes & fees
1 Oct - 2 Oct
Brand New Guest house

8. 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 AED 4,959
AED 7,865 total
includes taxes & fees
19 Sep - 20 Sep
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

9. Charming Vacation Home in Oak Bluffs.

Charming Vacation Home in Oak Bluffs.
Oak Bluffs
The price is AED 1,466
AED 3,044 total
includes taxes & fees
4 Oct - 5 Oct
Charming Vacation Home in Oak Bluffs.

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 AED 1,157
AED 3,118 total
includes taxes & fees
17 Sep - 18 Sep
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

11. 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 9,183
AED 14,056 total
includes taxes & fees
12 Oct - 13 Oct
Beautiful Estate with salt water pool & pond with kayaks

12. 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)
"Danny was a great host. Unit clean. Walking distance to everything"
United States
Alvin
The price is AED 1,102
AED 1,883 total
includes taxes & fees
1 Oct - 2 Oct
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

13. 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)
"We had a perfect pre-/off-season stay with plenty of sleeping space. The location is fantastic—right between Vineyard Haven and Edgartown—making it easy to bike to both, plus there’s a beach across the street. The WiFi wasn’t working when we first arrived, but the owner was incredibly responsive and went above and beyond to fix it quickly. We’ll definitely be back!"
United States
Bethann N.
The price is AED 1,161
AED 2,626 total
includes taxes & fees
17 Sep - 18 Sep
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

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 AED 1,102
AED 1,969 total
includes taxes & fees
12 Oct - 13 Oct
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.

15. The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (368 reviews)
"A"
United States
Zachary
The price is AED 789
AED 903 total
includes taxes & fees
20 Sep - 21 Sep
The Club at New Seabury

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

Charming 3 Bedroom Apartment . Walk to Ferry, Shops & Beach
Tisbury
The price is AED 1,466
AED 3,701 total
includes taxes & fees
1 Oct - 2 Oct
Charming 3 Bedroom Apartment . Walk to Ferry, Shops & Beach

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, (11 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
The price is AED 1,947
AED 5,124 total
includes taxes & fees
17 Sep - 18 Sep
New 4 BR house near center and beaches with bikes

18. 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 2,938
AED 4,685 total
includes taxes & fees
14 Oct - 15 Oct
The Seashell Cove - Martha's Vineyard

19. New Seabury Cape Condo + Pool & Beach Escape

New Seabury Cape Condo + Pool & Beach Escape
New Seabury
10.0 out of 10, Exceptional, (89 reviews)
"Great condo, great location. Fully equipped kitchen and awesome patio. "
United States
Jeff V.
The price is AED 360
AED 1,185 total
includes taxes & fees
30 Sep - 1 Oct
New Seabury Cape Condo + Pool & Beach Escape

20. New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL

New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL
Little Neck Bay
9.8 out of 10, Exceptional, (53 reviews)
"A wonderful home in a fabulous setting. The home has spacious & well laid out with a variety of beautiful outdoor spaces. Comfortable, with sufficient spaces inside and out; everyone had space to enjoy the property. We stayed for a week and never tired of the outdoor views. Convenient to great shopping and excellent beaches."
United States
Eric S.
The price is AED 1,928
AED 4,057 total
includes taxes & fees
2 Oct - 3 Oct
New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL
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

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 Victorian cottage overlooking downtown Oak Bluffs and the Harbor..

How many vacation rentals will I find in Oak Bluffs?

Choose from 267 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 Oak Bluffs Harbor.

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.