Oak Bluffs Holiday Rentals

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Our top choices for Oak Bluffs holiday rentals

Charming Vacation Home in Oak Bluffs.

Charming Vacation Home in Oak Bluffs.
Oak Bluffs
The price is NZ$1,276
includes taxes & fees
28 May - 29 May
Charming Vacation Home in Oak Bluffs.

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 NZ$1,123
includes taxes & fees
18 May - 19 May
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Oak Bluffs
10.0 out of 10, Exceptional, (7 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 NZ$2,028
includes taxes & fees
18 May - 19 May
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.4 out of 10, Exceptional, (3 reviews)
"This house was perfect for our getaway. Rebecca, the host, was extremely responsive and helpful during our trip. The house was as advertised. It was clean, well equipped, and the location was perfect as well "
United States
Louis R.
The price is NZ$1,484
includes taxes & fees
18 May - 19 May
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

Oak Bluffs - Quiet neighborhood

Oak Bluffs - Quiet neighborhood
Oak Bluffs
9.4 out of 10, Exceptional, (43 reviews)
"Perfectly situated!"
United States
Damani B.
The price is NZ$1,314
includes taxes & fees
20 May - 21 May
Oak Bluffs - Quiet neighborhood

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 NZ$1,123
includes taxes & fees
18 May - 19 May
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

Beautiful Estate with salt water pool & pond with kayaks

Beautiful Estate with salt water pool & pond with kayaks
Oak Bluffs
The price is NZ$5,293
includes taxes & fees
10 June - 11 June
Beautiful Estate with salt water pool & pond with kayaks

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 NZ$622
includes taxes & fees
20 May - 21 May
1 Mi to Ferry: 'sea Street Cottage' in Hyannis

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)
"We really enjoyed our stay at this property. The view was amazing and had our own private beach to lounge at!"
United States
Sean H.
The price is NZ$796
includes taxes & fees
4 June - 5 June
WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy

New Seabury Cape Condo + Pool & Beach Escape

New Seabury Cape Condo + Pool & Beach Escape
New Seabury
10.0 out of 10, Exceptional, (81 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 NZ$563
includes taxes & fees
21 May - 22 May
New Seabury Cape Condo + Pool & Beach Escape

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 NZ$766
includes taxes & fees
18 May - 19 May
Brand new! Lovely apartment-Vineyard Haven

Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis
Barnstable
8.6 out of 10, Excellent, (8 reviews)
"This was an amazing property and our host was awesome and checked in to make sure everything was going well. Would definitely stay here again! Thank you! "
United States
Kim
The price is NZ$845
includes taxes & fees
19 May - 20 May
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

Waterfront Gem: Hot Tub, Fire Pit & Private Beach! 3 Bed, 1.5 Baths, Sleeps 6

Waterfront Gem: Hot Tub, Fire Pit & Private Beach! 3 Bed, 1.5 Baths, Sleeps 6
Popponesset
10.0 out of 10, Exceptional, (189 reviews)
"great stay! fantastic location."
United States
Emily P.
The price is NZ$1,827
includes taxes & fees
23 May - 24 May
Waterfront Gem: Hot Tub, Fire Pit & Private Beach! 3 Bed, 1.5 Baths, Sleeps 6

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 NZ$618
includes taxes & fees
24 May - 25 May
Beach, marina, restaurants! 1 bedroom, living room, bath with private entrance!

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 NZ$1,039
includes taxes & fees
18 May - 19 May
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

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, (25 reviews)
"Wonderful stay, had everything we needed, Joy was very receptive to our messages. Thanks so much!"
United States
Alex K.
The price is NZ$384
includes taxes & fees
18 May - 19 May
Near Old Silver Beach Falmouth/Two bedroom , private bathroom and kitchenette

Falmouth Oasis

Falmouth Oasis
Falmouth
The price is NZ$833
includes taxes & fees
18 May - 19 May
Falmouth Oasis

Charming 3 bed room with magnificent views & large deck

Charming 3 bed room with magnificent views & large deck
Barnstable
8.6 out of 10, Excellent, (4 reviews)
"We had a great stay in Hyannis! The location is great for catching a ferry to Nantucket or the vineyard, and Main Street is within walking distance. The backyard is also very peaceful for a cup of coffee in the morning! "
United States
Meghan H.
The price is NZ$690
includes taxes & fees
18 May - 19 May
Charming 3 bed room with magnificent views & large deck

The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (355 reviews)
"Our stay was great and Amy at the front desk is a god send she was absolutely the best."
United States
Jasmine
The price is NZ$454
includes taxes & fees
18 May - 19 May
The Club at New Seabury

Edgartown Designer Cottage between Town & Beach.

Edgartown Designer Cottage between Town & Beach.
Katama
10.0 out of 10, Exceptional, (25 reviews)
"Wonderful week in MV! The cottage had everything we needed and was a great location to bike into town or to the beach. Would love to come back and stay again!"
United States
Lauren B.
The price is NZ$1,102
includes taxes & fees
18 May - 19 May
Edgartown Designer Cottage between Town & 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.
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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 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 NZ$384 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?

Charming 3 bed room with magnificent views & large deck: This holiday home rental outside of Oak Bluffs is equipped with a patio, air conditioning and free WiFi to help you feel comfortable during your stay. It has 3 bedrooms, as well as a kitchen with a stovetop, a microwave and an electric kettle, so that you can cook with friends or family.

How many holiday rentals will I find in Oak Bluffs?

Choose from 263 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.