Oak Bluffs Vacation Rentals

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Our top choices for Oak Bluffs vacation 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 CA $752
CA $1,656 total
includes taxes & fees
May 10 - May 11
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Charming Vacation Home in Oak Bluffs.

Charming Vacation Home in Oak Bluffs.
Oak Bluffs
The price is CA $545
CA $1,132 total
includes taxes & fees
May 27 - May 28
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, (88 reviews)
"The location of this property cannot be beat! Our second time staying here."
United States
Ashley S.
The price is CA $554
CA $917 total
includes taxes & fees
May 12 - May 13
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

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 $478
CA $1,221 total
includes taxes & fees
May 10 - May 11
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 CA $547
CA $1,090 total
includes taxes & fees
May 20 - May 21
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, (91 reviews)
"Great place to stay in Oak Bluffs"
United States
Stephen S.
The price is CA $584
CA $955 total
includes taxes & fees
May 10 - May 11
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 CA $195
CA $496 total
includes taxes & fees
May 14 - May 15
1 Mi to Ferry: 'sea Street Cottage' in Hyannis

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 CA $317
CA $362 total
includes taxes & fees
May 11 - May 12
The Club at New Seabury

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 $410
CA $846 total
includes taxes & fees
May 10 - May 11
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

4-bedroom house in lovely Edgartown..Centrally located

4-bedroom house in lovely Edgartown..Centrally located
Edgartown
The price is CA $307
CA $1,264 total
includes taxes & fees
May 11 - May 12
4-bedroom house in lovely Edgartown..Centrally located

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 CA $368
CA $743 total
includes taxes & fees
May 14 - May 15
Spacious and Bright , Very Close to Beach!

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 $294
CA $653 total
includes taxes & fees
Jun 4 - Jun 5
WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy

The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!

The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!
Onset
9.8 out of 10, Exceptional, (28 reviews)
"The Seaview suite was great! Clean and nicely appointed. Great views from the deck. "
United States
Lauren M.
The price is CA $368
CA $743 total
includes taxes & fees
May 11 - May 12
The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!

The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard
Katama
9.8 out of 10, Exceptional, (26 reviews)
"Nice and clean house, good location on the island, nice neighborhood "
United States
Eric C.
The price is CA $615
CA $1,135 total
includes taxes & fees
May 10 - May 11
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 CA $956
CA $1,667 total
includes taxes & fees
May 11 - May 12
New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!

Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site

Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
Tisbury
10.0 out of 10, Exceptional, (34 reviews)
"Great location and lovely cottage! Host was very helpful!"
United States
Meghan M.
The price is CA $751
CA $950 total
includes taxes & fees
Jun 8 - Jun 9
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site

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 $458
CA $899 total
includes taxes & fees
May 20 - May 21
Edgartown Designer Cottage between Town & Beach.

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, (188 reviews)
"great stay! fantastic location."
United States
Emily P.
The price is CA $409
CA $1,143 total
includes taxes & fees
May 17 - May 18
Waterfront Gem: Hot Tub, Fire Pit & Private Beach! 3 Bed, 1.5 Baths, Sleeps 6

Next to Cragville beach with warm sea water at a quiet and family friendly villa

Next to Cragville beach with warm sea water at a quiet and family friendly villa
Barnstable
9.4 out of 10, Exceptional, (14 reviews)
"The location of this property is really great! It’s close to two public beaches. But if you have allergies to mold, I would not recommend staying in this house."
United States
Heidi J.
The price is CA $287
CA $991 total
includes taxes & fees
Jun 4 - Jun 5
Next to Cragville beach with warm sea water at a quiet and family friendly villa

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 $409
CA $833 total
includes taxes & fees
May 27 - May 28
Amazing Onset Getaway in the Starfish Suite
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 260 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 Flying Horses Carousel.

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.