Holiday Rentals in Oak Bluffs

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Our top choices for Oak Bluffs holiday rentals

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 €1,028
includes taxes & fees
16 Apr - 17 Apr
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 €752
includes taxes & fees
16 Apr - 17 Apr
A NOSTALGIC SPACE! 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 €422
includes taxes & fees
18 Apr - 19 Apr
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

Oak Bluffs - Quiet neighborhood

Oak Bluffs - Quiet neighborhood
Oak Bluffs
9.4 out of 10, Exceptional, (43 reviews)
"Perfectly situated!"
United States
Damani B.
Oak Bluffs - Quiet neighborhood

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.
The price is €487
includes taxes & fees
30 Apr - 1 May
Perfect location! By Beach, Harbor & Town! Gorgeous Gingerbread Upstairs Aptmt

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 €422
includes taxes & fees
18 Apr - 19 Apr
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

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 €308
includes taxes & fees
8 May - 9 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, (3 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 €344
includes taxes & fees
16 Apr - 17 Apr
WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy

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 €528
includes taxes & fees
16 Apr - 17 Apr
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

Charming 3 bed room with magnificent views & large deck

Charming 3 bed room with magnificent views & large deck
Barnstable
8.0 out of 10, Very good, (3 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 €338
includes taxes & fees
16 Apr - 17 Apr
Charming 3 bed room with magnificent views & large deck

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 €437
includes taxes & fees
26 Apr - 27 Apr
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

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

Near Old Silver Beach Falmouth/Two bedroom , private bathroom and kitchenette
Falmouth
8.2 out of 10, Very good, (24 reviews)
"Wonderful stay, had everything we needed, Joy was very receptive to our messages. Thanks so much!"
United States
Alex K.
The price is €216
includes taxes & fees
17 Apr - 18 Apr
Near Old Silver Beach Falmouth/Two bedroom , private bathroom and kitchenette

Entire Hyannis Home - Near Downtown & Beaches

Entire Hyannis Home - Near Downtown & Beaches
Barnstable
10.0 out of 10, Exceptional, (1 review)
"We had a fantastic stay! The property was extremely clean from top to bottom, which immediately made us feel comfortable settling in. The beds and linens were incredibly comfortable and we all slept great.The location was also a huge plus. It is close to great restaurants, local events and plenty to do in the area, making it easy to get around and enjoy everything nearby.The host was extremely communicative and responsive, which made the whole experience smooth and stress free from booking...
United States
Bethany P.
Entire Hyannis Home - Near Downtown & Beaches

Spacious and Bright , Very Close to Beach!

Spacious and Bright , Very Close to Beach!
Onset
9.6 out of 10, Exceptional, (23 reviews)
"Amazing location, clean, spacious suite, great communication with the host, overall a great experience! "
United States
Bernadette C.
The price is €360
includes taxes & fees
30 Apr - 1 May
Spacious and Bright , Very Close to Beach!

The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard
Katama
9.8 out of 10, Exceptional, (25 reviews)
"Property was perfectly kept and very comfortable. "
United States
Steve D.
The price is €704
includes taxes & fees
25 Apr - 26 Apr
The Seashell Cove - Martha's Vineyard

New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!

New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!
Barnstable
10.0 out of 10, Exceptional, (31 reviews)
"It was a great stay and clean home. Recommend people to stay here"
United States
Charbel T.
The price is €827
includes taxes & fees
22 Apr - 23 Apr
New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!

Falmouth Oasis

Falmouth Oasis
Falmouth
The price is €415
includes taxes & fees
16 Apr - 17 Apr
Falmouth Oasis

Steps from Marina, beach, restaurants!

Steps from Marina, beach, restaurants!
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 €293
includes taxes & fees
20 Apr - 21 Apr
Steps from Marina, beach, restaurants!

Edgartown Designer Cottage between Town & Beach.

Edgartown Designer Cottage between Town & Beach.
Katama
10.0 out of 10, Exceptional, (24 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 €553
includes taxes & fees
1 May - 2 May
Edgartown Designer Cottage between Town & Beach.

Charming studio in tranquil Falmouth with AC

Charming studio in tranquil Falmouth with AC
Falmouth
The price is €179
includes taxes & fees
16 Apr - 17 Apr
Charming studio in tranquil Falmouth with AC
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, 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 €422 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 is located in the city centre, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals will I find in Oak Bluffs?

Choose from 253 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 Flying Horses Carousel.

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.