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Top Holiday Rentals in Oak Bluffs

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

6.2 out of 10, (24)
"The property is quiet, spacious and was within a walkable mile of downtown Oak Bluffs. The beds were comfortable. Plenty of clean linens and towels. The house could use some updating. The coffee maker, drinking glasses, and silverware need to be replaced with cleaner ones. And the torn portions of the sectional couch should be fixed. I would definitely stay at the property again."
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Walking to the beach. Bars and Restaurants.

9.6 out of 10, Exceptional, (4)
"The home was very nice and in a convenient location. Ana was very helpful and quick with communications during our stay. Would highly recommend for anyone traveling to Oak Bluffs! "
Walking to the beach. Bars and Restaurants.

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

10.0 out of 10, Exceptional, (7)
"Our kids and their friends had so much fun in the beautifully finished basement. Easy access to beach and ferry, would love to go back every year, the host was wonderful."
The price is £1,811
includes taxes & fees
1 Sept - 2 Sept
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Cozy Beach Cottage

9.8 out of 10, Exceptional, (50)
"The property was prepared, very thoughtful and had everything you could think of for a wonderful beach Island stay. The only downside was cable because I’m addicted to TV and I would’ve appreciated at least a smart TV that I could connect my own Netflix. "
Cozy Beach Cottage

THE PARK ESTATE! Your Martha's Vineyard Getaway!

9.8 out of 10, Exceptional, (17)
"The Park Estate is absolutely a phenomenal property. This estate has EVERYTHING you could ever want and need! The estate is well appointed, wonderfully located to travel throughout the area and the host, grounds keeper and everyone we communicated with was so kind, accessible and very informative. How we were so blessed to be able to rent this beautiful property at the last minute. It truly was fate. We look forward to future opportunities to stay here!"
THE PARK ESTATE! Your Martha's Vineyard Getaway!

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

The price is £475
includes taxes & fees
1 Sept - 2 Sept
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (326)
"Nice amenities. "
The Club at New Seabury

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (176)
"We really enjoyed the warm hospitality, the spacious rooms, great location right by the beach and great size pool. It’s close to downtown and walkable to a few restaurants. "
InnSeason Resorts Captain's Quarters

Sea Mist Resort

3.0 star property
8.8 out of 10, Excellent, (134)
"Great resort with suites, very cosy with great amenities, close to excellent beach and shopping."
The price is £122
includes taxes & fees
21 Sept - 22 Sept
Sea Mist Resort

Beachside Village Resort

3.0 star property
9.2 out of 10, Wonderful, (99)
"Great location! Nice property! "
Beachside Village Resort

Steps to the beach with an ocean view,

10.0 out of 10, Exceptional, (126)
"Nice home, great views and very relaxing stay."
Steps to the beach with an ocean view,

Steps to the Ocean! Perfect Location!!!

10.0 out of 10, Exceptional, (219)
"Perfect for a couple and two kids"
Steps to the Ocean! Perfect Location!!!

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

10.0 out of 10, Exceptional, (85)
"Great stay! "
Coastal chic meets French Provençal in this newly renovated oceanfront home.

Renovated Nantucket Style 2 Bed/2 Bath Cottage, Steps to Private Beach, Market..

8.6 out of 10, Excellent, (42)
"Great place for a summer vacation"
Renovated Nantucket Style 2 Bed/2 Bath Cottage, Steps to Private Beach, Market..

Southcape Resort Mashpee a Ramada by Wyndham

3.0 star property
8.6 out of 10, Excellent, (200)
"Enjoyed our stay."
Southcape Resort Mashpee a Ramada by Wyndham

Historic Home across from Monument Beach, Central A/C

10.0 out of 10, Exceptional, (90)
"Great location and easy walk to the beach."
Historic Home across from Monument Beach, Central A/C

Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath

8.4 out of 10, Very good, (20)
"So turn key and perfect for Month, Joy is an exceptional host and I’d recommend her place anytime"
The price is £170
includes taxes & fees
27 Aug - 28 Aug
Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath

Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!

9.6 out of 10, Exceptional, (40)
"Fantastic beach cabin in a nice location, close to Gay Head lighthouse and several beaches, including the dog-friendly Lobsterville. Good views, plenty of land, we had a good time!"
Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!

Relax & Unwind this Fall, at a very private & relaxing 1 bedroom 1 bath studio

10.0 out of 10, Exceptional, (6)
Relax & Unwind this Fall, at a very private & relaxing 1 bedroom 1 bath studio

The Costal Corner - Martha's Vineyard

2.0 star property
10.0 out of 10, Exceptional, (1)
"This property was great for our golf trip. The 3 bedrooms were exceptional "
The Costal Corner - Martha's Vineyard
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 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?

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs: This highly rated holiday home rental in Oak Bluffs offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Other favourite homes for rent in Oak Bluffs are MOST CHIC SPOT! Your Martha's Vineyard Getaway! and THE PARK ESTATE! Your Martha's Vineyard Getaway!.

How many holiday rentals will I find in Oak Bluffs?

Choose from 260 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 lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Oak Bluffs Fishing Pier. Other places in town to visit include Circuit Avenue and Oak Bluffs Harbor.

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.