colorful gingerbread houses, cottages in Oak Bluffs center, Martha's Vineyard island in Massachusetts USA on a sunny summer day

Oak Bluffs Vacation Rentals

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Our top choices for Oak Bluffs vacation rentals

Beautiful Estate with salt water pool & pond with kayaks

Beautiful Estate with salt water pool & pond with kayaks
Oak Bluffs
10.0 out of 10, Exceptional, (1 review)
"I can’t say enough about this beautiful property. pictures don’t do any justice for this piece of heaven. The flowers were everywhere , it’s so apparent that the property owners take such pride in this beautiful property. The place was spotless when we walked in the door. We met the owners on arrival , they surprised us with a beautiful ballon to celebrate my 50th birthday. My family enjoyed the pool and the fun Tiki. The outdoor fireplace was inviting after the sun went down. I was a little...
United States
Miriam D.
The price is CA $2,830
CA $4,505 total
includes taxes & fees
Jun 29 - Jun 30
Beautiful Estate with salt water pool & pond with kayaks

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Oak Bluffs
9.6 out of 10, Exceptional, (10 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 $955
CA $1,938 total
includes taxes & fees
Jun 24 - Jun 25
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
9.2 out of 10, Wonderful, (5 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 $573
CA $1,364 total
includes taxes & fees
Jun 25 - Jun 26
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
9.2 out of 10, Wonderful, (89 reviews)
"The location of this property cannot be beat! Our second time staying here."
United States
Ashley S.
The price is CA $605
CA $989 total
includes taxes & fees
Jun 24 - Jun 25
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

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 $672
CA $1,075 total
includes taxes & fees
Jun 30 - Jul 1
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 $202
CA $514 total
includes taxes & fees
Jun 28 - Jun 29
1 Mi to Ferry: 'sea Street Cottage' in Hyannis

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, (92 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 $425
CA $876 total
includes taxes & fees
Jul 12 - Jul 13
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

Sal's Place

Sal's Place
2.0 star property
Hyannis
The price is CA $1,911
CA $2,356 total
includes taxes & fees
Jun 27 - Jun 28
Sal's Place

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 $1,132
CA $1,939 total
includes taxes & fees
Jun 29 - Jun 30
New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!

Beach Pass Included!

Beach Pass Included!
Barnstable
Beach Pass Included!

Charming studio in tranquil Falmouth with AC

Charming studio in tranquil Falmouth with AC
Falmouth
The price is CA $224
CA $339 total
includes taxes & fees
Jun 29 - Jun 30
Charming studio in tranquil Falmouth with AC

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)
"Great stay! Close to the beach!"
United States
Heather L.
Next to Cragville beach with warm sea water at a quiet and family friendly villa

The SandDollar Suite - Private Deck with Gorgeous Views of Onset Beach

The SandDollar Suite - Private Deck with Gorgeous Views of Onset Beach
Onset
9.4 out of 10, Exceptional, (10 reviews)
"Top floor is the best! "
United States
Alyssa A.
The price is CA $324
CA $699 total
includes taxes & fees
Jun 24 - Jun 25
The SandDollar Suite - Private Deck with Gorgeous Views of Onset Beach

4-bedroom house in lovely Edgartown..Centrally located

4-bedroom house in lovely Edgartown..Centrally located
Edgartown
10.0 out of 10, Exceptional, (1 review)
"Awesome place! Clean! Great communication! Clean and well stocked. A pleasure to deal with."
United States
Kelly H.
The price is CA $637
CA $1,715 total
includes taxes & fees
Jun 24 - Jun 25
4-bedroom house in lovely Edgartown..Centrally located

The Sky-High Beach House: Panoramic Waterfront views

The Sky-High Beach House: Panoramic Waterfront views
Fairhaven
The price is CA $345
CA $711 total
includes taxes & fees
Jul 14 - Jul 15
The Sky-High Beach House: Panoramic Waterfront views

5 Mi to Beach: Cape Cod Getaway w/ Grill

5 Mi to Beach: Cape Cod Getaway w/ Grill
3.0 star property
Sandwich
The price is CA $311
CA $847 total
includes taxes & fees
Jun 28 - Jun 29
5 Mi to Beach: Cape Cod Getaway w/ Grill

Backyard Retreat / 5 Min > Beach & Main St

Backyard Retreat / 5 Min > Beach & Main St
Fairhaven
The price is CA $363
CA $1,006 total
includes taxes & fees
Jun 24 - Jun 25
Backyard Retreat / 5 Min > Beach & Main St

serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower

serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower
West Tisbury
The price is CA $665
CA $1,408 total
includes taxes & fees
Jul 11 - Jul 12
serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower

Coastal Retreat: Game Room,BBQ Fire Pit & BeachNEARBY

Coastal Retreat: Game Room,BBQ Fire Pit & BeachNEARBY
Barnstable
The price is CA $975
CA $2,236 total
includes taxes & fees
Jul 1 - Jul 2
Coastal Retreat: Game Room,BBQ Fire Pit & BeachNEARBY

Barefoot Walk to Beaches • Extended Family Friendly • Fast WiFi • Pet Friendly

Barefoot Walk to Beaches • Extended Family Friendly • Fast WiFi • Pet Friendly
Hyannis
9.6 out of 10, Exceptional, (52 reviews)
"We had a great trip and stay. The location is perfect for walking to three different beaches but still on a quiet, shady street. The house was well stocked and included a shed full of everything we could need for our beach days. "
United States
Julia H.
The price is CA $2,378
CA $3,999 total
includes taxes & fees
Jul 10 - Jul 11
Barefoot Walk to Beaches • Extended Family Friendly • Fast WiFi • Pet Friendly
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?

Quaint, ranch style home in Oak Bluffs with central air: Visitors give good reviews to this Oak Bluffs vacation home rental, which is located near the beach and has a balcony, a garden, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Other favorite homes for rent in Oak Bluffs are Bright old-world cottage with two porches & large yard - walk to town & beaches and Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs.

How many vacation rentals will I find in Oak Bluffs?

Choose from 267 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.