Oak Bluffs Holiday Rentals

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Our top choices for Oak Bluffs holiday rentals

Walk to Beach & Lighthouse: Oak Bluffs Studio!

Walk to Beach & Lighthouse: Oak Bluffs Studio!
Oak Bluffs
7.6 out of 10, Good, (4 reviews)
"Very accommodating early check in and great communication "
United States
Katelyn K.
The price is AU$478
includes taxes & fees
7 June - 8 June
Walk to Beach & Lighthouse: Oak Bluffs Studio!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.0 out of 10, Wonderful, (4 reviews)
"The host was very responsive.We definitely recommend this house as family friendly."
United States
Karen M.
The price is AU$1,335
includes taxes & fees
7 June - 8 June
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Oak Bluffs
9.6 out of 10, Exceptional, (9 reviews)
"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."
United States
Swathanthra M.
The price is AU$1,892
includes taxes & fees
7 June - 8 June
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

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, (91 reviews)
"Great place to stay in Oak Bluffs"
United States
Stephen S.
The price is AU$965
includes taxes & fees
8 June - 9 June
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

Perfect location! By Beach, Harbor & Town! Gorgeous Gingerbread Upstairs Aptmt

Perfect location! By Beach, Harbor & Town! Gorgeous Gingerbread Upstairs Aptmt
Oak Bluffs
10.0 out of 10, Exceptional, (46 reviews)
"Great accommodations and a perfect location for the beach, shopping and great food."
United States
Hugh M.
Perfect location! By Beach, Harbor & Town! Gorgeous Gingerbread Upstairs Aptmt

Beautiful Estate with salt water pool & pond with kayaks

Beautiful Estate with salt water pool & pond with kayaks
Oak Bluffs
The price is AU$4,346
includes taxes & fees
10 June - 11 June
Beautiful Estate with salt water pool & pond with kayaks

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, (88 reviews)
"The location of this property cannot be beat! Our second time staying here."
United States
Ashley S.
The price is AU$1,006
includes taxes & fees
7 June - 8 June
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy

WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy
Sandwich
10.0 out of 10, Exceptional, (4 reviews)
"The view was breathe taking and the space was small yet comforting. The little label reminders were very helpful. The suggestion for things to were great. Wish week had more time to try the different places. Was an overall amazing stay would stay again."
United States
Theresa M.
WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy

Beach, marina, restaurants! 1 bedroom, living room, bath with private entrance!

Beach, marina, restaurants! 1 bedroom, living room, bath with private entrance!
Wareham
9.8 out of 10, Exceptional, (12 reviews)
"Beautiful space, wonderful location, amazing host. If I could give 100 stars I would! "
United States
Jaimie
The price is AU$420
includes taxes & fees
16 June - 17 June
Beach, marina, restaurants! 1 bedroom, living room, bath with private entrance!

Newly Renovated Hyannis Home w/ Fire Pit & Yard

Newly Renovated Hyannis Home w/ Fire Pit & Yard
Hyannis
10.0 out of 10, Exceptional, (2 reviews)
"Really enjoyed our stay. Very clean and comfortable home. The communication with the owners was excellent. We would definitely visit again. "
United States
Shawn B.
Newly Renovated Hyannis Home w/ Fire Pit & Yard

New Seabury Cape Condo + Pool & Beach Escape

New Seabury Cape Condo + Pool & Beach Escape
New Seabury
10.0 out of 10, Exceptional, (83 reviews)
"Host was super organized with clear instructions and easy check-in. The condo was well appointed and beautifully decorated. We enjoyed our brief stay!"
United States
Gina P.
The price is AU$459
includes taxes & fees
17 June - 18 June
New Seabury Cape Condo + Pool & Beach Escape

1 Mi to Ferry: 'sea Street Cottage' in Hyannis

1 Mi to Ferry: 'sea Street Cottage' in Hyannis
3.0 star property
Hyannis
The price is AU$509
includes taxes & fees
7 June - 8 June
1 Mi to Ferry: 'sea Street Cottage' in Hyannis

Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
New Seabury
8.6 out of 10, Excellent, (91 reviews)
"This was the perfect home for our weekend getaway! Joyce was wonderful to work with. Perfect location and beautiful home, just what we needed!"
United States
Courtney R.
The price is AU$865
includes taxes & fees
9 June - 10 June
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

Open all year! Relaxation & privacy at this cozy 1 bedroom 1 bath studio.

Open all year! Relaxation & privacy at this cozy 1 bedroom 1 bath studio.
Falmouth
10.0 out of 10, Exceptional, (10 reviews)
"A very nice stay. Relaxing and quiet - we would highly recommend!"
United States
David C.
The price is AU$570
includes taxes & fees
7 June - 8 June
Open all year! Relaxation & privacy at this cozy 1 bedroom 1 bath studio.

Near Old Silver Beach Falmouth-Two bedroom, private bathroom and kitchenette

Near Old Silver Beach Falmouth-Two bedroom, private bathroom and kitchenette
Falmouth
8.4 out of 10, Very good, (26 reviews)
"Very nice location in North Falmouth where things feel timeless. The only disadvantage was there is no living/sitting room. You can sit in the kitchen or be in the bedrooms. Host was attentive and available."
United States
Michelle
The price is AU$450
includes taxes & fees
20 June - 21 June
Near Old Silver Beach Falmouth-Two bedroom, private bathroom and kitchenette

Brand new! Lovely apartment-Vineyard Haven

Brand new! Lovely apartment-Vineyard Haven
Tisbury
9.8 out of 10, Exceptional, (25 reviews)
"Lovely and all brand new accommodation's that are clean and comfy! A quiet location too! "
United States
Nancy K.
The price is AU$668
includes taxes & fees
22 June - 23 June
Brand new! Lovely apartment-Vineyard Haven

The SandDollar Suite - Private Deck with Gorgeous Views of Onset Beach

The SandDollar Suite - Private Deck with Gorgeous Views of Onset Beach
Onset
9.4 out of 10, Exceptional, (10 reviews)
"Top floor is the best! "
United States
Alyssa A.
The price is AU$732
includes taxes & fees
7 June - 8 June
The SandDollar Suite - Private Deck with Gorgeous Views of Onset Beach

Spacious and Bright , Very Close to Beach!

Spacious and Bright , Very Close to Beach!
Onset
9.6 out of 10, Exceptional, (24 reviews)
"Amazing location, clean, spacious suite, great communication with the host, overall a great experience! "
United States
Bernadette C.
The price is AU$769
includes taxes & fees
7 June - 8 June
Spacious and Bright , Very Close to Beach!

Amazing Onset Getaway in the Starfish Suite

Amazing Onset Getaway in the Starfish Suite
Onset
9.6 out of 10, Exceptional, (25 reviews)
"This location is really wonderful. What a cute town and the house had everything we needed. "
United States
Tony and Beck V.
The price is AU$906
includes taxes & fees
7 June - 8 June
Amazing Onset Getaway in the Starfish Suite

Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area

Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area
Falmouth
10.0 out of 10, Exceptional, (9 reviews)
"A beautiful home conveniently located-very clean Nd comfortable for 6 long time friends."
United States
Linda W.
The price is AU$864
includes taxes & fees
18 June - 19 June
Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area
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

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, 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 favourite 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 depend 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 AU$372 per night. Entering your travel dates in the search wizard might find you 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?

Quaint, ranch style home in Oak Bluffs with central air: This highly rated holiday home rental in Oak Bluffs is located near the beach, and has a balcony, a garden and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Other favourite homes for rent in Oak Bluffs are Bright old-world cottage with two porches & large yard - walk to town & beaches and Beautiful Estate with salt water pool & pond with kayaks .

How many holiday rentals will I find in Oak Bluffs?

Choose from 266 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 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 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.