Oak Bluffs Holiday Rentals

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Our top choices for Oak Bluffs holiday rentals

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 HK$2,344
HK$5,201 total
includes taxes & fees
11 Feb - 12 Feb
Oak Bluffs - Quiet neighborhood

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 HK$2,734
HK$6,981 total
includes taxes & fees
8 Feb - 9 Feb
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 HK$2,344
HK$4,162 total
includes taxes & fees
8 Mar - 9 Mar
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 HK$4,297
HK$9,468 total
includes taxes & fees
8 Feb - 9 Feb
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, (88 reviews)
"The location of this property cannot be beat! Our second time staying here."
United States
Ashley S.
The price is HK$2,344
HK$4,162 total
includes taxes & fees
8 Mar - 9 Mar
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (349 reviews)
"Everything was superb, accommodations, check in service, check out service!!"
United States
Dianna
The price is HK$1,279
HK$1,464 total
includes taxes & fees
15 Feb - 16 Feb
The Club at New Seabury

InnSeason Resorts Captain's Quarters

InnSeason Resorts Captain's Quarters
3.5 star property
Falmouth Heights
9.8 out of 10, Exceptional, (197 reviews)
"This is my go to hotel when I’m in Falmouth. Always clean and the staff are very friendly. The one bedroom units are very nice!"
United States
Jeff
The price is HK$1,013
HK$1,159 total
includes taxes & fees
8 Feb - 9 Feb
InnSeason Resorts Captain's Quarters

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 HK$1,172
HK$3,049 total
includes taxes & fees
8 Feb - 9 Feb
WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy

Spacious and Bright , Very Close to Beach!

Spacious and Bright , Very Close to Beach!
Onset
9.6 out of 10, Exceptional, (22 reviews)
"Amazing location, clean, spacious suite, great communication with the host, overall a great experience! "
United States
Bernadette C.
The price is HK$1,118
HK$3,012 total
includes taxes & fees
7 Feb - 8 Feb
Spacious and Bright , Very Close to Beach!

Falmouth Oasis

Falmouth Oasis
Falmouth
The price is HK$1,125
HK$3,478 total
includes taxes & fees
10 Feb - 11 Feb
Falmouth Oasis

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 HK$766
HK$1,565 total
includes taxes & fees
28 Feb - 1 Mar
Near Old Silver Beach Falmouth/Two bedroom , private bathroom and kitchenette

Entire Hyannis Home Near Downtown & Beaches

Entire Hyannis Home Near Downtown & Beaches
Barnstable
The price is HK$902
HK$3,224 total
includes taxes & fees
26 Feb - 27 Feb
Entire Hyannis Home Near Downtown & Beaches

Amazing Onset Getaway in the Starfish Suite

Amazing Onset Getaway in the Starfish Suite
Onset
9.6 out of 10, Exceptional, (25 reviews)
"The property was very nice and in a great location."
United States
Judith H.
The price is HK$1,188
HK$3,309 total
includes taxes & fees
7 Feb - 8 Feb
Amazing Onset Getaway in the Starfish Suite

Hyannis Hideaway in Cape Cod

Hyannis Hideaway in Cape Cod
Barnstable
10.0 out of 10, Exceptional, (2 reviews)
"Awesome private property, close to Main Street and Craigsville beach. My friends and I stay in Hyannis every 4th of July and this home was super accommodating for groups and close to everything. Great stay would recommend. "
United States
Hunter W.
The price is HK$2,777
HK$4,859 total
includes taxes & fees
17 Feb - 18 Feb
Hyannis Hideaway in Cape Cod

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)
"Property needs a refresh."
United States
Paul B.
The price is HK$2,344
HK$4,846 total
includes taxes & fees
8 Mar - 9 Mar
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC

Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC
Barnstable
10.0 out of 10, Exceptional, (5 reviews)
"Very nice property in a quiet and convenient location. Private backyard with outdoor shower. Interior was completely updated with very nice furnishings and appliances. All in all a great home that we will definitely return to. "
United States
Jim C.
The price is HK$2,063
HK$5,080 total
includes taxes & fees
7 Feb - 8 Feb
Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC

Lakefront Stunning Cape Cod Views w Private Lake Beach - Backyard is the Lake !

Lakefront Stunning Cape Cod Views w Private Lake Beach - Backyard is the Lake !
Barnstable
10.0 out of 10, Exceptional, (1 review)
"My family and I thoroughly enjoyed our week long stay at the beautiful property. There were 12 of us and we were extremely comfortable, with plenty of space to gather and sleep. The property sits on a quiet pond, that was perfect for swimming and canoeing. We had our own little piece of paradise. There are canoes for use, several decks for lounging and was within a short distance to various shops and a grocery store just a few minutes away. The host was in constant contact with us, making sure...
United States
Madilynn B.
The price is HK$3,692
HK$8,607 total
includes taxes & fees
7 Feb - 8 Feb
Lakefront Stunning Cape Cod Views w Private Lake Beach - Backyard is the Lake !

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Falmouth
10.0 out of 10, Exceptional, (212 reviews)
"This beautiful well-appointed home was the perfect spot for a girlfriend’s getaway. Walkable to the shops and restaurants, nice big rooms for chats, and a great kitchen island to congregate around for breakfast. We loved our time here!"
United States
Annemarie G.
The price is HK$1,266
HK$3,862 total
includes taxes & fees
10 Feb - 11 Feb
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Spring Escape in Hatchville – Sleeps 6 + Dogs!

Spring Escape in Hatchville – Sleeps 6 + Dogs!
Falmouth
10.0 out of 10, Exceptional, (11 reviews)
"Enjoyed our stay. Everything was clean and well kept. "
United States
Lynn S.
Spring Escape in Hatchville – Sleeps 6 + Dogs!

TABOR SUITE, IN THE MARION VILLAGE

TABOR SUITE, IN THE MARION VILLAGE
Marion
9.0 out of 10, Wonderful, (2 reviews)
"Very good"
United States
Karl D.
The price is HK$1,102
HK$2,906 total
includes taxes & fees
8 Feb - 9 Feb
TABOR SUITE, IN THE MARION VILLAGE
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

Search for holiday rentals in Oak Bluffs on Expedia! You can easily find your home rentals, villas, holiday apartments in Oak Bluffs using one of the methods below:

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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?

MOST CHIC SPOT! Your Martha's Vineyard Getaway!: 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. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Another good choice for your trip to Oak Bluffs is Victorian cottage overlooking downtown Oak Bluffs and the Harbor..

How many holiday rentals will I find in Oak Bluffs?

Choose from 248 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.