Oak Bluffs Vacation Rentals

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Our top choices for Oak Bluffs vacation rentals

Lovely two bedroom apartment with indoor fireplace

Lovely two bedroom apartment with indoor fireplace
Oak Bluffs
10.0 out of 10, Exceptional, (7 reviews)
"Great stay, flexible and responsive host. Difficult location, however, as it was not centrally located or easy to access transportation, etc."
United States
Aviva M.
The price is CA $340
CA $1,119 total
includes taxes & fees
May 19 - May 20
Lovely two bedroom apartment with indoor fireplace

Charming Vacation Home in Oak Bluffs.

Charming Vacation Home in Oak Bluffs.
Oak Bluffs
The price is CA $494
CA $1,069 total
includes taxes & fees
May 26 - May 27
Charming Vacation Home in Oak Bluffs.

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 CA $756
CA $1,666 total
includes taxes & fees
May 19 - May 20
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 CA $481
CA $1,229 total
includes taxes & fees
May 19 - May 20
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 CA $557
CA $922 total
includes taxes & fees
May 19 - May 20
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.
The price is CA $550
CA $1,097 total
includes taxes & fees
May 21 - May 22
Oak Bluffs - Quiet neighborhood

Beautiful Estate with salt water pool & pond with kayaks

Beautiful Estate with salt water pool & pond with kayaks
Oak Bluffs
The price is CA $2,750
CA $4,262 total
includes taxes & fees
Jun 11 - Jun 12
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 CA $557
CA $922 total
includes taxes & fees
May 19 - May 20
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)
"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 CA $289
CA $648 total
includes taxes & fees
Jun 4 - Jun 5
WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy

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 CA $197
CA $499 total
includes taxes & fees
May 20 - May 21
1 Mi to Ferry: 'sea Street Cottage' in Hyannis

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 CA $135
CA $463 total
includes taxes & fees
May 21 - May 22
New Seabury Cape Condo + Pool & Beach Escape

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 CA $186
CA $693 total
includes taxes & fees
May 19 - May 20
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

Serene Haven w/ No Shared Spaces | Cape Cod

Serene Haven w/ No Shared Spaces | Cape Cod
Marston Mills
10.0 out of 10, Exceptional, (16 reviews)
"Marston Hills is a great location for getting to many great areas of Cape Cod. The house was very clean and nicely furnished. "
United States
Dana S.
The price is CA $234
CA $409 total
includes taxes & fees
May 19 - May 20
Serene Haven w/ No Shared Spaces | 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)
"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 CA $413
CA $851 total
includes taxes & fees
May 19 - May 20
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

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 CA $288
CA $611 total
includes taxes & fees
May 20 - May 21
Brand new! Lovely apartment-Vineyard Haven

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)
"Perfect location for the ferry and some great restaurants. We walked everywhere. Super comfortable to relax after being gone all day. Bathroom was hotel quality. Great view from the deck. "
United States
Rose T.
The price is CA $220
CA $582 total
includes taxes & fees
May 19 - May 20
Charming 3 bed room with magnificent views & large deck

Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth

Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth
Falmouth
9.6 out of 10, Exceptional, (11 reviews)
"Really beautiful place with a lot of space and a very helpful host"
United States
Gokul K.
The price is CA $413
CA $1,169 total
includes taxes & fees
May 19 - May 20
Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth

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)
"Wonderful stay, had everything we needed, Joy was very receptive to our messages. Thanks so much!"
United States
Alex K.
The price is CA $147
CA $315 total
includes taxes & fees
May 19 - May 20
Near Old Silver Beach Falmouth/Two bedroom , private bathroom and kitchenette

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 CA $370
CA $779 total
includes taxes & fees
May 25 - May 26
Amazing Onset Getaway in the Starfish Suite

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 CA $461
CA $905 total
includes taxes & fees
May 19 - May 20
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Oak Bluffs. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.