A coastal cliff with a sandy beach and the ocean.

Dukes County Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Top Cities in Dukes County

Our top choices for Dukes County 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. 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.

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. 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!

5. 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.

6. 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

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

New 4 BR house near center and beaches with bikes
Katama
10.0 out of 10, Exceptional, (7 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
The price is CA $743
CA $2,048 total
includes taxes & fees
Sep 7 - Sep 8
New 4 BR house near center and beaches with bikes

8. 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

9. 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

10. Walk to Town/Golf Club - Renovated Edgartown Home

Walk to Town/Golf Club - Renovated Edgartown Home
Edgartown
10.0 out of 10, Exceptional, (46 reviews)
"Great house in a great location—just a short, easy walk to downtown Edgartown"
United States
Steven M.
The price is CA $820
CA $1,583 total
includes taxes & fees
Sep 2 - Sep 3
Walk to Town/Golf Club - Renovated Edgartown Home

11. 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

12. 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

13. Wooded Vineyard Retreat Near Beaches & Town

Wooded Vineyard Retreat Near Beaches & Town
Edgartown
The price is CA $778
CA $1,537 total
includes taxes & fees
Aug 18 - Aug 19
Wooded Vineyard Retreat Near Beaches & Town

14. The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard
Katama
9.8 out of 10, Exceptional, (28 reviews)
"Nice and clean house, good location on the island, nice neighborhood "
United States
Eric C.
The price is CA $1,051
CA $1,699 total
includes taxes & fees
Sep 6 - Sep 7
The Seashell Cove - Martha's Vineyard

15. Walk to downtown Edgartown in quiet neighborhood - Perfect Location!

Walk to downtown Edgartown in quiet neighborhood - Perfect Location!
Edgartown
10.0 out of 10, Exceptional, (5 reviews)
"One of the most well equipped vacation rentals I’ve stayed in. A simple, but well curated place. Thank you to our hosts!"
United States
Anonymous traveller
The price is CA $1,051
CA $1,788 total
includes taxes & fees
Aug 31 - Sep 1
Walk to downtown Edgartown in quiet neighborhood - Perfect Location!

16. 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

17. Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site

Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
Tisbury
10.0 out of 10, Exceptional, (37 reviews)
"Great place, awesome location!"
United States
Connor B.
The price is CA $1,190
CA $1,519 total
includes taxes & fees
Sep 6 - Sep 7
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site

18. 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!

19. 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 3 - Sep 4
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

20. 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!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Dukes County Hotel Reviews

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 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.