Oak Bluffs Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

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 NZ$4,035
includes taxes & fees
1 Sept - 2 Sept
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

The price is NZ$1,056
includes taxes & fees
1 Sept - 2 Sept
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

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!

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (325)
"A great unique and quiet place, very close to Boston."
The Club at New Seabury

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (176)
"Just a quick weekend away. Great location for beach lovers. Also excellent retaurants "
InnSeason Resorts Captain's Quarters

Beachside Village Resort

3.0 star property
9.4 out of 10, Exceptional, (96)
"Great location! Nice property! "
The price is NZ$607
includes taxes & fees
19 Aug - 20 Aug
Beachside Village Resort

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..

Sea Mist Resort

3.0 star property
8.8 out of 10, Excellent, (133)
"Great resort with suites, very cosy with great amenities, close to excellent beach and shopping."
The price is NZ$308
includes taxes & fees
9 Sept - 10 Sept
Sea Mist Resort

Steps to the beach with an ocean view,

10.0 out of 10, Exceptional, (125)
"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, (218)
"Perfect for a couple and two kids"
Steps to the Ocean! Perfect Location!!!

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

Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome

8.8 out of 10, Excellent, (33)
"Great spot for a get away. Private with easy access to activities."
Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome

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.

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 NZ$379
includes taxes & fees
28 Aug - 29 Aug
Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath

Renovated cottage steps from private beach with backyard, grill, bay views, AC

7.6 out of 10, Good, (4)
"Rather disappointed with quality of mattresses and overall bedroom furnishings and linens given the cost of rental. Window unit air conditioners were old, noisy and prevented view of water. While property was clean on the inside, outside foliage was overgrown and patio had not been cleaned or swept in sometime. "
Renovated cottage steps from private beach with backyard, grill, bay views, AC

3 Mi to Beaches & Golfing: Family Gem in Cotuit

9.4 out of 10, Exceptional, (6)
3 Mi to Beaches & Golfing: Family Gem in Cotuit

Gorgeous Cottage steps from the beach

8.4 out of 10, Very good, (16)
"Great place to stay we loved it"
Gorgeous Cottage steps from the beach

Waterfront Mashpee 5Bed/3Bath house with AC and WiFi w/ Private Beach

10.0 out of 10, Exceptional, (1)
"House was roomie, comfortable, with a gorgeous view. "
Waterfront Mashpee 5Bed/3Bath house with AC and WiFi w/ Private Beach
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.
Save an average of 15% on thousands of hotels when you're signed in

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.