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

Oak Bluffs Vacation Rentals

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Oak Bluffs vacation rentals

Property grounds

1. Make Lasting Memories In This Adorable Vineyard Cottage!

Make Lasting Memories In This Adorable Vineyard Cottage!
Oak Bluffs
9.8 out of 10, Exceptional, (153 reviews)
"Cute, compact, and had everything we needed for ourstay. I'd definitely stay there again."
United States
Karen C.
$457 nightly
The price is $510
Sep 2 - Sep 3
Total with taxes and fees
Make Lasting Memories In This Adorable Vineyard Cottage!
Smart TV

2. 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, (92 reviews)
"Memorial Day weekend on the Vineyard was perfect."
United States
Cassandra
$623 nightly
The price is $696
Sep 1 - Sep 2
Total with taxes and fees
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
Terrace/patio

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

Walk to Beach & Lighthouse: Oak Bluffs Studio!
Oak Bluffs
8.8 out of 10, Excellent, (8 reviews)
"Very accommodating early check in and great communication "
United States
Katelyn K.
$561 nightly
The price is $627
Aug 22 - Aug 23
Total with taxes and fees
Walk to Beach & Lighthouse: Oak Bluffs Studio!
Exterior

4. Perfect location! By Beach, Harbor & Town! Gorgeous Gingerbread Upstairs Aptmt

Perfect location! By Beach, Harbor & Town! Gorgeous Gingerbread Upstairs Aptmt
Oak Bluffs
10.0 out of 10, Exceptional, (47 reviews)
"Great accommodations and a perfect location for the beach, shopping and great food."
United States
Hugh M.
$651 nightly
The price is $727
Aug 26 - Aug 27
Total with taxes and fees
Perfect location! By Beach, Harbor & Town! Gorgeous Gingerbread Upstairs Aptmt
Property grounds

5. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Oak Bluffs
6.8 out of 10, (9 reviews)
"We had a perfect pre-/off-season stay with plenty of sleeping space. The location is fantastic—right between Vineyard Haven and Edgartown—making it easy to bike to both, plus there’s a beach across the street. The WiFi wasn’t working when we first arrived, but the owner was incredibly responsive and went above and beyond to fix it quickly. We’ll definitely be back!"
United States
Bethann N.
$567 nightly
The price is $633
Sep 7 - Sep 8
Total with taxes and fees
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Exterior

6. 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, (6 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
$1,266 nightly
The price is $1,414
Sep 6 - Sep 7
Total with taxes and fees
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
Coffee/tea maker, fridge, microwave, oven

7. Brand New Guest house

Brand New Guest house
Oak Bluffs
10.0 out of 10, Exceptional, (5 reviews)
"This is a new, beautiful and tastefully decorated 2 bedroom one bathroom house with a really nice big yard. Owner was very responsive and We had everything we needed for an enjoyable stay!"
United States
Elizabeth O.
$1,011 nightly
The price is $1,129
Aug 24 - Aug 25
Total with taxes and fees
Brand New Guest house
Sun loungers, beach towels

8. Charming Vacation Home in Oak Bluffs.

Charming Vacation Home in Oak Bluffs.
Oak Bluffs
$1,983 nightly
The price is $2,215
Aug 23 - Aug 24
Total with taxes and fees
Charming Vacation Home in Oak Bluffs.
TV, fireplace, books

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

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.6 out of 10, Exceptional, (7 reviews)
"The host was very responsive.We definitely recommend this house as family friendly."
United States
Karen M.
$1,377 nightly
The price is $1,538
Sep 1 - Sep 2
Total with taxes and fees
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Exterior

10. 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.
$3,749 nightly
The price is $4,188
Aug 30 - Aug 31
Total with taxes and fees
Beautiful Estate with salt water pool & pond with kayaks
Interior

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, (11 reviews)
"TLDR: House is nice,"
United States
Rachel
$3,537 nightly
The price is $3,951
Aug 23 - Aug 24
Total with taxes and fees
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Interior

12. 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, (94 reviews)
"Great place to stay in Oak Bluffs"
United States
Stephen S.
$680 nightly
The price is $760
Aug 24 - Aug 25
Total with taxes and fees
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Terrace/patio

13. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
$858 nightly
The price is $958
Sep 1 - Sep 2
Total with taxes and fees
Walk to Beach! Oak Bluffs Home & Studio
TV

14. Small One Bedroom Private Cottage on Large Quiet Property.

Small One Bedroom Private Cottage on Large Quiet Property.
Tisbury
10.0 out of 10, Exceptional, (16 reviews)
"My wife and I really enjoyed our stay. This Cottage is the perfect size for a couple. We enjoyed the beautiful quiet setting that was close to town. The host thought of everything and the cottage was so clean it felt like we were the first people who ever rented the unit. We walked into town several times and loved the location. Do not hesitate to rent this cottage. "
United States
Timothy G.
$457 nightly
The price is $510
Aug 23 - Aug 24
Total with taxes and fees
Small One Bedroom Private Cottage on Large Quiet Property.
TV

15. New Seabury Cape Condo + Pool & Beach Escape

New Seabury Cape Condo + Pool & Beach Escape
New Seabury
10.0 out of 10, Exceptional, (85 reviews)
"Great condo, great location. Fully equipped kitchen and awesome patio. "
United States
Jeff V.
$291 nightly
The price is $333
Aug 17 - Aug 18
Total with taxes and fees
New Seabury Cape Condo + Pool & Beach Escape
Interior

16. Brand new! Lovely apartment-Vineyard Haven

Brand new! Lovely apartment-Vineyard Haven
Tisbury
9.8 out of 10, Exceptional, (30 reviews)
"Lovely and all brand new accommodation's that are clean and comfy! A quiet location too! "
United States
Nancy K.
$626 nightly
The price is $700
Aug 27 - Aug 28
Total with taxes and fees
Brand new! Lovely apartment-Vineyard Haven
Terrace/patio

17. WATERFRONT Downtown Cottage w/ Beach

WATERFRONT Downtown Cottage w/ Beach
Tisbury
10.0 out of 10, Exceptional, (51 reviews)
"Very beautiful, very clean with incredible views of the Vineyard Haven harbor views"
United States
John M.
$1,285 nightly
The price is $1,435
Aug 20 - Aug 21
Total with taxes and fees
WATERFRONT Downtown Cottage w/ Beach
Coffee/tea maker, fridge, microwave, oven

18. Walking-distance to town, shops, restaurants & ferry!

Walking-distance to town, shops, restaurants & ferry!
Tisbury
10.0 out of 10, Exceptional, (25 reviews)
"I rented this for my staff, and they said it was the best place they have stayed on Martha's Vineyard."
United States
else r.
$1,084 nightly
The price is $1,211
Aug 20 - Aug 21
Total with taxes and fees
Walking-distance to town, shops, restaurants & ferry!
Exterior

19. NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
Tisbury
10.0 out of 10, Exceptional, (18 reviews)
"We had an amazing time at this beautiful home. Great, clean space to spend an evening visit with friends and family. Great location with easy access around the island. Would highly recommend! "
United States
Jennifer T.
$1,308 nightly
The price is $1,461
Aug 17 - Aug 18
Total with taxes and fees
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
Interior

20. 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, (6 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.
$446 nightly
The price is $498
Sep 2 - Sep 3
Total with taxes and fees
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
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

AutoCamp Cape Cod

AutoCamp Cape Cod

10/10 Excellent
"Everything was easy and we loved our stay! Definitely recommend it and we will come back again!"
Xuezhu 1-night trip
Posted 7 hours ago
AutoCamp Cape Cod

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 $321 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?

Victorian cottage overlooking downtown Oak Bluffs and the Harbor.: Visitors give good reviews to this Oak Bluffs vacation home rental, which offers a fireplace, a balcony, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 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 Quaint, ranch style home in Oak Bluffs with central air and Bright old-world cottage with two porches & large yard - walk to town & beaches.

How many vacation rentals will I find in Oak Bluffs?

Choose from 278 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.