Oak Bluffs Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Oak Bluffs vacation rentals

Sun loungers, beach towels

Charming Vacation Home in Oak Bluffs.

Charming Vacation Home in Oak Bluffs.
Oak Bluffs
The price is ￥57,004
￥123,429 total
includes taxes & fees
May 28 - May 29
Charming Vacation Home in Oak Bluffs.
Interior

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 ￥64,290
￥106,389 total
includes taxes & fees
May 19 - May 20
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Interior

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 ￥87,307
￥192,385 total
includes taxes & fees
May 18 - May 19
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
TV, fireplace, books

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 ￥55,559
￥141,850 total
includes taxes & fees
May 18 - May 19
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Terrace/patio

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 ￥63,496
￥126,601 total
includes taxes & fees
May 20 - May 21
Oak Bluffs - Quiet neighborhood
Smart TV

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 ￥64,290
￥106,389 total
includes taxes & fees
May 18 - May 19
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
Exterior

Beautiful Estate with salt water pool & pond with kayaks

Beautiful Estate with salt water pool & pond with kayaks
Oak Bluffs
The price is ￥317,480
￥487,432 total
includes taxes & fees
Jun 10 - Jun 11
Beautiful Estate with salt water pool & pond with kayaks
Cottage (2 Bedrooms) | Front of property

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 ￥22,700
￥57,651 total
includes taxes & fees
May 20 - May 21
1 Mi to Ferry: 'sea Street Cottage' in Hyannis
Interior

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 ￥33,335
￥73,215 total
includes taxes & fees
Jun 4 - Jun 5
WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy
TV

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 ￥15,558
￥52,689 total
includes taxes & fees
May 21 - May 22
New Seabury Cape Condo + Pool & Beach Escape
Interior

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 ￥34,002
￥71,847 total
includes taxes & fees
May 18 - May 19
Brand new! Lovely apartment-Vineyard Haven
Beach nearby

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 ￥21,430
￥79,270 total
includes taxes & fees
May 19 - May 20
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis
Dining

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 ￥79,211
￥174,228 total
includes taxes & fees
May 23 - May 24
Waterfront Gem: Hot Tub, Fire Pit & Private Beach! 3 Bed, 1.5 Baths, Sleeps 6
Beach nearby, sun loungers, beach towels

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 ￥22,716
￥58,355 total
includes taxes & fees
May 24 - May 25
Beach, marina, restaurants! 1 bedroom, living room, bath with private entrance!
Property grounds

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 ￥47,622
￥98,652 total
includes taxes & fees
May 18 - May 19
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
Interior

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 ￥18,890
￥38,334 total
includes taxes & fees
May 21 - May 22
Near Old Silver Beach Falmouth/Two bedroom , private bathroom and kitchenette
Exterior

Falmouth Oasis

Falmouth Oasis
Falmouth
The price is ￥28,573
￥78,484 total
includes taxes & fees
May 18 - May 19
Falmouth Oasis
Property grounds

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 ￥23,811
￥65,041 total
includes taxes & fees
May 18 - May 19
Charming 3 bed room with magnificent views & large deck
Private beach nearby, beach bar

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 ￥36,773
￥42,086 total
includes taxes & fees
May 26 - May 27
The Club at New Seabury
Marina

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 ￥53,178
￥104,438 total
includes taxes & fees
May 18 - May 19
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Oak Bluffs Hotel Reviews

Falmouth Inn

Falmouth Inn

10/10 Excellent
"Spotless room👍love the location near shops and restaurants."
Gail 4-night trip
Posted 1 hour ago
Falmouth Inn

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:

  • View our selection of featured holiday rentals in Oak Bluffs
  • Use the map to find apartments and other holiday homes in the Oak Bluffs neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Oak Bluffs while they last

Look no further and take a look at our great range of rental properties in Oak Bluffs!

Frequently asked questions

Can I find vacation rentals in Oak Bluffs?

Yes, you can find vacation rentals in Oak Bluffs near Flying Horses Carousel, or you can go with a more secluded option if you're looking for extra privacy while you relax. 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 vacation rentals in Oak Bluffs?

Charming 3 bed room with magnificent views & large deck: This vacation 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 you can cook with friends or family.

How many vacation rentals will I find in Oak Bluffs?

Choose from 263 Expedia vacation rentals in Oak Bluffs for a memorable vacation.

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 vacation rentals like in Oak Bluffs?

Vacation rentals are private accommodations you can reserve for several days or longer in Oak Bluffs. Vacation rentals feature extras such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, vacation rentals can provide a sense of privacy away from public hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for a small group gathering.