A row of colorful, historic houses with a central path.

Oak Bluffs Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Oak Bluffs vacation rentals

A living room with a flat-screen TV on a stand, a black leather chair, and a sofa. There are two windows with curtains, one of which offers a view of the sea.

1. 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, (97 reviews)
"Memorial Day weekend on the Vineyard was perfect."
United States
Cassandra
$446 nightly
The price is $498
Oct 18 - Oct 19
Total with taxes and fees
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
A single-story house with a covered porch, a hammock, and a brick pathway leading to the front door.

2. Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
Oak Bluffs
9.8 out of 10, Exceptional, (10 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
$1,224 nightly
The price is $1,367
Oct 17 - Oct 18
Total with taxes and fees
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
An outdoor seating area with Adirondack chairs and a table, surrounded by trees.

3. Walk to Beach & Lighthouse: Oak Bluffs Studio!

Walk to Beach & Lighthouse: Oak Bluffs Studio!
Oak Bluffs
7.6 out of 10, Good, (14 reviews)
"The unit was clean and sufficient for 2 people. Outside could use some attention."
United States
Donna R.
$561 nightly
The price is $627
Oct 20 - Oct 21
Total with taxes and fees
Walk to Beach & Lighthouse: Oak Bluffs Studio!
A spacious living room with a wooden staircase, a fireplace, and a leather sofa.

4. < 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs
Oak Bluffs
7.4 out of 10, Good, (3 reviews)
"House was neat architectural wise and family history of home ownership was very cool. However, listing noted there was a washer/dryer and there was not. House also noted that there was a fire pit and it was rusted through. Screen door handles were broken, windows need repair, and house has animals living in the downstairs bathroom wall. House needs updates to charge what was being charged a night. In addition, there was a Nor’easter that hit the island and we attempted to contact the host to let...
United States
Kate K.
$841 nightly
The price is $939
Oct 17 - Oct 18
Total with taxes and fees
< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

5. Oak Bluffs 4BR • 5 Min Drive to Downtown

Oak Bluffs 4BR • 5 Min Drive to Downtown
Oak Bluffs
10.0 out of 10, Exceptional, (1 review)
"This place was just what we needed! Would definitely stay again. Cozy and feels very homey! Thanks!"
United States
Chris S.
$667 nightly
The price is $745
Nov 11 - Nov 12
Total with taxes and fees
Oak Bluffs 4BR • 5 Min Drive to Downtown
A circular stone patio with Adirondack chairs and a small table in a forested area.

6. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Oak Bluffs
7.0 out of 10, Good, (12 reviews)
"Loved this spot. Perfect central island location. Fantastic owner with an incredible response time. Would recommend this property to all5 stars"
United States
Eli R.
$640 nightly
The price is $715
Oct 20 - Oct 21
Total with taxes and fees
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Room

7. Sunlit Studio Retreat with Incredible Outdoor Deck on Martha’s Vineyard

Sunlit Studio Retreat with Incredible Outdoor Deck on Martha’s Vineyard
Oak Bluffs
$264 nightly
The price is $295
Nov 4 - Nov 5
Total with taxes and fees
Sunlit Studio Retreat with Incredible Outdoor Deck on Martha’s Vineyard
A spacious living area with a high ceiling, a dining table, and a kitchen area.

8. A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.6 out of 10, Exceptional, (10 reviews)
"A clean accommodating space with an accommodating host - I recommended!"
United States
Collins E.
$965 nightly
The price is $1,078
Oct 17 - Oct 18
Total with taxes and fees
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
A backyard with a seating area, a white fence, and a variety of plants.

9. Delightful 3-bedroom house with AC in Oak Bluffs

Delightful 3-bedroom house with AC in Oak Bluffs
Oak Bluffs
$1,025 nightly
The price is $1,145
Oct 30 - Oct 31
Total with taxes and fees
Delightful 3-bedroom house with AC in Oak Bluffs
A room with a view of the sea through large windows, a wooden deck, and a pier with structures.

10. 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, (98 reviews)
"Danny was a great host. Unit clean. Walking distance to everything"
United States
Alvin
$480 nightly
The price is $536
Oct 23 - Oct 24
Total with taxes and fees
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
A modern interior with a wooden staircase, a kitchen area, and a living space with a sofa and coffee table.

11. MOST CHIC SPOT! Your Martha's Vineyard Getaway!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Oak Bluffs
9.8 out of 10, Exceptional, (12 reviews)
"This was an excellent stay at a beautiful property in Oak Bluffs! Rebecca was a great host who provided clear instructions and helped answer questions in a timely manner. Rooms were spacious, most tastefully decorated and we had everything that we needed. I definitely recommend staying here to have an unparalleled experience of the Vineyard."
United States
Priyanka D.
$1,980 nightly
The price is $2,212
Oct 17 - Oct 18
Total with taxes and fees
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
A deck with a portable grill, blue Adirondack chairs, and a wooden table.

12. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
$836 nightly
The price is $934
Oct 20 - Oct 21
Total with taxes and fees
Walk to Beach! Oak Bluffs Home & Studio
A two-story house with a stone facade, a covered patio, and a well-maintained garden.

13. 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, (3 reviews)
"Brenda and Derek were amazing hosts. They have a beautifully landscaped property with all the amenities needed for a relaxing family vacation. They are super responsive and take a lot of pride in giving their guests a top-notch experience. We will definitely consider staying at their properties again."
United States
Lamar A.
$3,426 nightly
The price is $3,827
Oct 18 - Oct 19
Total with taxes and fees
Beautiful Estate with salt water pool & pond with kayaks
A modern kitchen with a marble countertop, a central island, and a hanging light fixture.

14. Brand new! Lovely apartment-Vineyard Haven

Brand new! Lovely apartment-Vineyard Haven
Tisbury
10.0 out of 10, Exceptional, (33 reviews)
"Fabulous property! Clean and very comfy."
United States
Claudia
$484 nightly
The price is $541
Oct 18 - Oct 19
Total with taxes and fees
Brand new! Lovely apartment-Vineyard Haven
A view through a window with a wooden frame, overlooking a garden with various plants and a body of water in the background.

15. Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.

Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
Tisbury
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful view of the lagoon; ideal place for a couple or single. Leisurely walk to town and close to public transportation."
United States
Adrienne W.
$497 nightly
The price is $555
Oct 23 - Oct 24
Total with taxes and fees
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
A coastal hotel with multiple beachside rooms, a large covered area, and a beach with umbrellas.

16. The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (371 reviews)
"The New Seabury resort is beautiful & has excellent customer service. The 4/5 stars is because the unit we stayed in needs some updating. However, the layout, cleanliness, & location is good."
United States
Kathleen
$173 nightly
The price is $198
Nov 1 - Nov 2
Total with taxes and fees
The Club at New Seabury
A residential area with a well-maintained lawn, a stone retaining wall, and a two-story house with a blue door.

17. New 4 BR house near center and beaches with bikes

New 4 BR house near center and beaches with bikes
Katama
9.8 out of 10, Exceptional, (13 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
$1,492 nightly
The price is $1,667
Oct 18 - Oct 19
Total with taxes and fees
New 4 BR house near center and beaches with bikes
A spacious living area with wooden beams, a dining table, and a sofa.

18. The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard
Katama
9.8 out of 10, Exceptional, (31 reviews)
"Nice and clean house, good location on the island, nice neighborhood "
United States
Eric C.
$1,000 nightly
The price is $1,117
Oct 18 - Oct 19
Total with taxes and fees
The Seashell Cove - Martha's Vineyard
A beach with clear water and a sandy shore.

19. New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL

New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL
Little Neck Bay
9.8 out of 10, Exceptional, (54 reviews)
"We had the best week at 67 Tide Run! The property is gorgeous. We enjoyed kayaking and fishing from the dock. It was plenty big enough for our family of 10. We are going to miss the views. It’s perfect! You cannot go wrong booking Jamie’s home."
United States
cindy w.
$906 nightly
The price is $1,037
Oct 30 - Oct 31
Total with taxes and fees
New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL
A modern living room with a sofa, chairs, a coffee table, and a dining area.

20. New Seabury Cape Condo + Pool & Beach Escape

New Seabury Cape Condo + Pool & Beach Escape
New Seabury
10.0 out of 10, Exceptional, (92 reviews)
"Great condo, great location. Fully equipped kitchen and awesome patio. "
United States
Jeff V.
$280 nightly
The price is $321
Oct 22 - Oct 23
Total with taxes and fees
New Seabury Cape Condo + Pool & Beach Escape
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

Summercamp

Summercamp

10/10 Excellent
"Property was in an ideal location. Walking distance to all the key spots. Very clean and very supportive desk personnel. We had 1st floor room which was great. I saw others struggling with luggage up stairs. I did like the fact they had huge lockers for early arrivals in case room was quite available. My only complaint was the bathroom sink. Very small but after 2 days it was acceptable"
Ernestine 4-night trip
Posted 1 hour ago
Summercamp

Find out more about Oak Bluffs

Everything you need to know about Oak Bluffs vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Oak Bluffs vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oak Bluffs vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Oak Bluffs vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oak Bluffs. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Oak Bluffs in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $198 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Oak Bluffs rentals

At Expedia, we put the best Oak Bluffs vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Oak Bluffs rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oak Bluffs vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oak Bluffs. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

Coastal Retreat | Walk to Inkwell Beach, Dining & Flying Horses Carousel: Visitors give good reviews to this Oak Bluffs vacation home rental, which is located near the beach and has a balcony, a garden, and a barbecue grill 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 you can cook with friends or family. Other favorite homes for rent in Oak Bluffs are Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs and Quaint, ranch style home in Oak Bluffs with central air.

How many vacation rentals will I find in Oak Bluffs?

Choose from 270 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.