Holiday Rentals in Oak Bluffs

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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 Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

9.4 out of 10, Exceptional, (84)
"Close to buses, restaurants and ferries. 10/10, we would stay again."
The price is €565
includes taxes & fees
1 Sept - 2 Sept
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

Walk to Beach & Lighthouse: Oak Bluffs Studio!

7.4 out of 10, Good, (3)
"Very accommodating early check in and great communication "
The price is €356
includes taxes & fees
26 Sept - 27 Sept
Walk to Beach & Lighthouse: Oak Bluffs Studio!

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 €1,295
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!

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 €141
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 Ocean! Perfect Location!!!

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

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,

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.

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 €177
includes taxes & fees
28 Aug - 29 Aug
Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath

Southcape Resort Mashpee a Ramada by Wyndham

3.0 star property
8.6 out of 10, Excellent, (201)
"Enjoyed our stay."
Southcape Resort Mashpee a Ramada by Wyndham

Steps from Marina, beach, restaurants!

9.8 out of 10, Exceptional, (11)
"Property was as described. This was only a quick stay & wish we had a longer visit. Location was great with lots to do. Owner was available to answer any questions "
The price is €227
includes taxes & fees
2 Sept - 3 Sept
Steps from Marina, beach, restaurants!

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

10.0 out of 10, Exceptional, (7)
Relax & Unwind this Fall, at a very private & relaxing 1 bedroom 1 bath studio

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!!

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

8.6 out of 10, Excellent, (44)
"Great place for a summer vacation"
Renovated Nantucket Style 2 Bed/2 Bath Cottage, Steps to Private Beach, Market..

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
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

Find out more about Oak Bluffs

Find out more about Oak Bluffs

Everything you need to know about Oak Bluffs holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oak Bluffs holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oak Bluffs holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Oak Bluffs holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oak Bluffs. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oak Bluffs holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oak Bluffs holiday rentals we have selected for you start as low as €141 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Oak Bluffs rentals

At Expedia, we put the best Oak Bluffs holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Oak Bluffs rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oak Bluffs holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oak Bluffs. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 259 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.