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

Oak Bluffs Vacation Rentals

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Our top choices for Oak Bluffs vacation rentals

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.
The price is CA $350
CA $712 total
includes taxes & fees
Sep 2 - Sep 3
Make Lasting Memories In This Adorable Vineyard Cottage!

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
The price is CA $596
CA $975 total
includes taxes & fees
Sep 1 - Sep 2
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

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.
The price is CA $461
CA $875 total
includes taxes & fees
Aug 30 - Aug 31
Walk to Beach & Lighthouse: Oak Bluffs Studio!

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.
The price is CA $553
CA $1,011 total
includes taxes & fees
Aug 26 - Aug 27
Perfect location! By Beach, Harbor & Town! Gorgeous Gingerbread Upstairs Aptmt

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.
The price is CA $353
CA $883 total
includes taxes & fees
Sep 3 - Sep 4
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

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.
The price is CA $610
CA $1,982 total
includes taxes & fees
Sep 6 - Sep 7
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

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.
The price is CA $694
CA $1,583 total
includes taxes & fees
Aug 24 - Aug 25
Brand New Guest house

8. Charming Vacation Home in Oak Bluffs.

Charming Vacation Home in Oak Bluffs.
Oak Bluffs
The price is CA $2,101
CA $3,109 total
includes taxes & fees
Aug 25 - Aug 26
Charming Vacation Home in Oak Bluffs.

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.
The price is CA $1,198
CA $2,156 total
includes taxes & fees
Sep 1 - Sep 2
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

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.
The price is CA $4,205
CA $6,240 total
includes taxes & fees
Aug 30 - Aug 31
Beautiful Estate with salt water pool & pond with kayaks

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
The price is CA $3,783
CA $5,542 total
includes taxes & fees
Aug 23 - Aug 24
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

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.
The price is CA $666
CA $1,063 total
includes taxes & fees
Sep 3 - Sep 4
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

13. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is CA $545
CA $1,343 total
includes taxes & fees
Sep 1 - Sep 2
Walk to Beach! Oak Bluffs Home & Studio

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.
The price is CA $420
CA $715 total
includes taxes & fees
Aug 23 - Aug 24
Small One Bedroom Private Cottage on Large Quiet Property.

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.
The price is CA $137
CA $465 total
includes taxes & fees
Aug 17 - Aug 18
New Seabury Cape Condo + Pool & Beach Escape

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.
The price is CA $612
CA $1,060 total
includes taxes & fees
Aug 27 - Aug 28
Brand new! Lovely apartment-Vineyard Haven

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.
The price is CA $1,366
CA $2,012 total
includes taxes & fees
Aug 20 - Aug 21
WATERFRONT Downtown Cottage w/ Beach

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

Walking-distance to town, shops, restaurants & ferry!
Tisbury
10.0 out of 10, Exceptional, (26 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.
The price is CA $1,330
CA $1,697 total
includes taxes & fees
Aug 20 - Aug 21
Walking-distance to town, shops, restaurants & ferry!

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.
The price is CA $1,114
CA $2,047 total
includes taxes & fees
Aug 17 - Aug 18
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

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.
The price is CA $420
CA $751 total
includes taxes & fees
Sep 2 - Sep 3
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

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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oak Bluffs vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oak Bluffs vacation rentals we have selected for you start as low as CA $450 per night. Entering your travel dates in the search wizard 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. 

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.