A coastal cliff with a sandy beach and the ocean.

Dukes County Vacation Rentals

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Top Cities in Dukes County

An aerial view of a coastal area with a lighthouse, a sandy beach, and a marina.
Vacation RentalsVacation Rentals

Edgartown

Edgartown
A dock with boats, a small wooden structure, and a forested shoreline.
Vacation RentalsVacation Rentals

Chilmark

Chilmark

Our top choices for Dukes County vacation rentals

A view through a window with a wooden frame, overlooking a garden with various plants and a body of water in the background.

1. 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, (10 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 $412
CA $736 total
includes taxes & fees
Oct 21 - Oct 22
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
A modern kitchen with a marble countertop, a central island, and a hanging light fixture.

2. Brand new! Lovely apartment-Vineyard Haven

Brand new! Lovely apartment-Vineyard Haven
Tisbury
10.0 out of 10, Exceptional, (32 reviews)
"This property is quiet yet close enough to the business areas. Very clean, well maintained lovely unit with balcony. The host Joziane commutated with us from minutes after the booking to the end of stay, very helpful."
United States
Unspecified U.
The price is CA $381
CA $760 total
includes taxes & fees
Oct 10 - Oct 11
Brand new! Lovely apartment-Vineyard Haven
A rocky beach with clear water, a sandy shore, and a hilly landscape in the background.

3. 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.
The price is CA $511
CA $1,197 total
includes taxes & fees
Oct 4 - Oct 5
Oak Bluffs 4BR • 5 Min Drive to Downtown
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.

4. 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, (96 reviews)
"Memorial Day weekend on the Vineyard was perfect."
United States
Cassandra
The price is CA $426
CA $758 total
includes taxes & fees
Oct 4 - Oct 5
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
An outdoor seating area with Adirondack chairs and a table, surrounded by trees.

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

Walk to Beach & Lighthouse: Oak Bluffs Studio!
Oak Bluffs
7.8 out of 10, Good, (12 reviews)
"The unit was clean and sufficient for 2 people. Outside could use some attention."
United States
Donna R.
The price is CA $467
CA $886 total
includes taxes & fees
Oct 4 - Oct 5
Walk to Beach & Lighthouse: Oak Bluffs Studio!
A residential area with a well-maintained lawn, a stone retaining wall, and a two-story house with a blue door.

6. 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, (11 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
The price is CA $752
CA $2,066 total
includes taxes & fees
Oct 11 - Oct 12
New 4 BR house near center and beaches with bikes
A circular stone patio with Adirondack chairs and a small table in a forested area.

7. 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.
The price is CA $448
CA $1,015 total
includes taxes & fees
Oct 4 - Oct 5
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
A single-story house with a covered porch, a hammock, and a brick pathway leading to the front door.

8. 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, (9 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
The price is CA $565
CA $1,940 total
includes taxes & fees
Oct 2 - Oct 3
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
A spacious living area with a high ceiling, a dining table, and a kitchen area.

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, (9 reviews)
"The host was very responsive.We definitely recommend this house as family friendly."
United States
Karen M.
The price is CA $703
CA $1,530 total
includes taxes & fees
Oct 4 - Oct 5
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
A spacious living room with a wooden staircase, a fireplace, and a leather sofa.

10. < 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.
The price is CA $620
CA $1,333 total
includes taxes & fees
Oct 3 - Oct 4
< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs
A spacious living area with wooden beams, a dining table, and a sofa.

11. 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.
The price is CA $1,064
CA $1,720 total
includes taxes & fees
Oct 18 - Oct 19
The Seashell Cove - Martha's Vineyard
A two-story house with a swimming pool, a covered patio, and a fenced backyard.

12. Cozy efficiency apartment/heated pool

Cozy efficiency apartment/heated pool
Chilmark
9.6 out of 10, Exceptional, (26 reviews)
"This is a great property for an individual or a couple looking to explore the island!"
United States
Jillian G.
The price is CA $562
CA $854 total
includes taxes & fees
Oct 13 - Oct 14
Cozy efficiency apartment/heated pool
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.
The price is CA $3,548
CA $5,277 total
includes taxes & fees
Oct 18 - Oct 19
Beautiful Estate with salt water pool & pond with kayaks
A room with a view of the sea through large windows, a wooden deck, and a pier with structures.

14. 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
The price is CA $426
CA $758 total
includes taxes & fees
Oct 7 - Oct 8
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.

15. 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.
The price is CA $1,916
CA $3,164 total
includes taxes & fees
Oct 2 - Oct 3
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
An outdoor seating area with Adirondack chairs and a table, surrounded by trees.

16. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is CA $552
CA $1,325 total
includes taxes & fees
Oct 4 - Oct 5
Walk to Beach! Oak Bluffs Home & Studio
A coastal hotel with multiple beachside rooms, a large covered area, and a beach with umbrellas.

17. 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
The price is CA $228
CA $261 total
includes taxes & fees
Nov 1 - Nov 2
The Club at New Seabury
A pool area with lounge chairs and flags.

18. The Cove at Yarmouth by Westgate Resorts

The Cove at Yarmouth by Westgate Resorts
3.0 star property
West Yarmouth
9.2 out of 10, Wonderful, (268 reviews)
"P Indoor pool and hot tub loved and the outdoor Shack was great"
United States
BELKIS
The price is CA $162
CA $186 total
includes taxes & fees
Oct 25 - Oct 26
The Cove at Yarmouth by Westgate Resorts
A modern living room with a sofa, chairs, a coffee table, and a dining area.

19. New Seabury Cape Condo + Pool & Beach Escape

New Seabury Cape Condo + Pool & Beach Escape
New Seabury
10.0 out of 10, Exceptional, (90 reviews)
"Great condo, great location. Fully equipped kitchen and awesome patio. "
United States
Jeff V.
The price is CA $125
CA $457 total
includes taxes & fees
Oct 4 - Oct 5
New Seabury Cape Condo + Pool & Beach Escape
A boat docked at a concrete pier with a sandy shore in the background.

20. Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!
Seconsett Island
10.0 out of 10, Exceptional, (44 reviews)
"Great stay!"
United States
Kian S.
The price is CA $248
CA $653 total
includes taxes & fees
Oct 7 - Oct 8
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!
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 Dukes County Hotel Reviews

Summercamp

Summercamp

10/10 Excellent
"Staff was very kind and helpful! Property is in a great location and def has a fun summer camp vibe - the lobby and common areas are so inviting!"
Jennifer 4-night trip
Posted 11 hours ago
Summercamp

Find out more about Dukes County

Everything you need to know about Dukes County 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 Dukes County 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 Dukes County vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Dukes County vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Dukes County. 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 Dukes County 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 Dukes County vacation rentals we have selected for you start as low as CA $758 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Dukes County rentals

At Expedia, we put the best Dukes County 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 Dukes County 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 Dukes County 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 Dukes County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.