A coastal cliff with a sandy beach and the ocean.

Vacation Homes in Dukes County

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Top Cities in Dukes County

Our top choices for Dukes County vacation homes

1. Quaint home across from bike paths with large furnished deck, grill, & W/D

Quaint home across from bike paths with large furnished deck, grill, & W/D
West Tisbury
10.0 out of 10, Exceptional, (8 reviews)
"Very clean house, very family friendly, loved the games closet and proximity to both sides of the island. Would love to stay here again if we have the opportunity. "
United States
Kathryn W.
Quaint home across from bike paths with large furnished deck, grill, & W/D

2. 4-bedroom house in lovely Edgartown..Centrally located

4-bedroom house in lovely Edgartown..Centrally located
Edgartown
10.0 out of 10, Exceptional, (3 reviews)
"Awesome place! Clean! Great communication! Clean and well stocked. A pleasure to deal with."
United States
Kelly H.
4-bedroom house in lovely Edgartown..Centrally located

3. Coastal Retreat | Walk to Inkwell Beach, Dining & Flying Horses Carousel

Coastal Retreat | Walk to Inkwell Beach, Dining & Flying Horses Carousel
Oak Bluffs
10.0 out of 10, Exceptional, (1 review)
Coastal Retreat | Walk to Inkwell Beach, Dining & Flying Horses Carousel

4. Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!

Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!
Aquinnah
9.8 out of 10, Exceptional, (54 reviews)
"Amazing stay again. Already booked another."
United States
Brad G.
Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!

5. Cozy getaway in a central location w/ a full kitchen & furnished deck

Cozy getaway in a central location w/ a full kitchen & furnished deck
Oak Bluffs
6.0 out of 10, (1 review)
"It was a good location"
United States
Barbara G.
Cozy getaway in a central location w/ a full kitchen & furnished deck

6. Oak Bluffs - Quiet neighborhood

Oak Bluffs - Quiet neighborhood
Oak Bluffs
9.2 out of 10, Wonderful, (50 reviews)
"Perfectly situated!"
United States
Damani B.
Oak Bluffs - Quiet neighborhood

7. COZY 3 BR/2 BA CAPE COD IN QUIET NEIGHBORHOOD. CLOSE TO OB CENTER AND LAGOON.

COZY 3 BR/2 BA CAPE COD IN QUIET NEIGHBORHOOD. CLOSE TO OB CENTER AND LAGOON.
Oak Bluffs
10.0 out of 10, Exceptional, (11 reviews)
"Wonderful stay at this charming Oak Bluffs home right by the Lagoon. The home was just as described and the hosts were warm and responsive. We will definitely be back!"
United States
Barbara B.
COZY 3 BR/2 BA CAPE COD IN QUIET NEIGHBORHOOD. CLOSE TO OB CENTER AND LAGOON.

8. Victorian cottage overlooking downtown Oak Bluffs and the Harbor.

Victorian cottage overlooking downtown Oak Bluffs and the Harbor.
Oak Bluffs
9.0 out of 10, Wonderful, (8 reviews)
"Check in was simple. The house was as represented and perfectly located. The host was responsive and there were great neighbors. We enjoyed our stay and would definitely visit again."
United States
L R.
Victorian cottage overlooking downtown Oak Bluffs and the Harbor.

9. Private cottage nestled in center of the Vineyard

Private cottage nestled in center of the Vineyard
West Tisbury
10.0 out of 10, Exceptional, (66 reviews)
"We thoroughly enjoyed our stay, the cottage’s central location made it easy for us to enjoy the entire island! We would definitely recommend this to anyone is looking for seclusion and relaxation. "
United States
Keith O.
Private cottage nestled in center of the Vineyard

10. Nana's Backyard Treehouse with deck, electric/gas grills, kitchenette

Nana's Backyard Treehouse with deck, electric/gas grills, kitchenette
West Tisbury
Nana's Backyard Treehouse with deck, electric/gas grills, kitchenette

11. Charming 4-bedroom house with AC and WiFi in beautiful Edgartown

Charming 4-bedroom house with AC and WiFi in beautiful Edgartown
Edgartown
10.0 out of 10, Exceptional, (7 reviews)
"The home was spacious. Set in a quiet location but less than 10 minutes drive to downtown Edgartown, with easy access to other towns. Lisa was responsive and the checkout process was the easiest I’ve experienced across any stay of mine."
United States
Omari E.
Charming 4-bedroom house with AC and WiFi in beautiful Edgartown

12. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Oak Bluffs
6.6 out of 10, (11 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 AED 1,161
AED 2,605 total
includes taxes & fees
31 Aug - 1 Sep
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

13. Coastal Contemporary in Katama / South Beach/ Edgartown / Bike Paths/ Air Field

Coastal Contemporary in Katama / South Beach/ Edgartown / Bike Paths/ Air Field
Katama
10.0 out of 10, Exceptional, (45 reviews)
"Fantastic place!"
United States
Robert O.
Coastal Contemporary in Katama / South Beach/ Edgartown / Bike Paths/ Air Field

14. Spacious 4BR+ Katama Home-Edgartown South Beach Area-Open Aug 14-28 2027 w ferry

Spacious 4BR+ Katama Home-Edgartown South Beach Area-Open Aug 14-28 2027 w ferry
Katama
9.8 out of 10, Exceptional, (59 reviews)
"We all had a wonderful time. Everything was great. The bikes were a very nice addition. We really enjoyed using them. The location was very convenient. The house was excellent and we would love to stay here again."
United States
Stephanie H.
Spacious 4BR+ Katama Home-Edgartown South Beach Area-Open Aug 14-28 2027 w ferry

15. Downtown brand new construction 3 bed & 3 bath

Downtown brand new construction 3 bed & 3 bath
Tisbury
10.0 out of 10, Exceptional, (5 reviews)
"Owner went above and beyond for their guests and all communication was swift and effective. Everything just as described. Highly recommend and would def stay again. "
United States
L B.
Downtown brand new construction 3 bed & 3 bath

16. Quaint, ranch style home in Oak Bluffs with central air

Quaint, ranch style home in Oak Bluffs with central air
Oak Bluffs
8.4 out of 10, Very Good, (5 reviews)
"Exactly as expected. Very clean and was nice and cool upon arrival. Well stocked and had everything we needed for our stay, including towels, linens, toiletries, and cleaning supplies. Very quick responses from property management. Phenomenal location. Perfect for anyone looking for a solid, clean and comfortable camp on the island. "
United States
Siobhan W.
Quaint, ranch style home in Oak Bluffs with central air

17. Spacious home for entertaining, centrally located to beach, ferry, and airport.

Spacious home for entertaining, centrally located to beach, ferry, and airport.
Edgartown
10.0 out of 10, Exceptional, (5 reviews)
"We loved this home, its amenities and how easy the process was! We would recommend it to anyone!! Thank you!"
United States
Timothy R.
Spacious home for entertaining, centrally located to beach, ferry, and airport.

18. Luxury Loft Historic Center Oak Bluffs

Luxury Loft Historic Center Oak Bluffs
Oak Bluffs
9.6 out of 10, Exceptional, (51 reviews)
"Would stay here again! "
United States
Stacey N.
Luxury Loft Historic Center Oak Bluffs

19. Sanctuary House: An ocean-view farmhouse retreat

Sanctuary House: An ocean-view farmhouse retreat
West Tisbury
10.0 out of 10, Exceptional, (42 reviews)
"This pet-friendly farm was ideal for our family vacation! The hot tub was a hit, and you can’t beat the view from almost every room in the house. We loved visiting the horses and chickens, taking hikes along the trails right near the house and playing in the large yard. The beds were comfy and the hosts were helpful and quick to respond. We would absolutely stay here again! "
United States
Tracy B.
Sanctuary House: An ocean-view farmhouse retreat

20. Soulas Martha's Vineyard, Walk to Inkwell Beach & Town

Soulas Martha's Vineyard, Walk to Inkwell Beach & Town
Oak Bluffs
10.0 out of 10, Exceptional, (6 reviews)
"I would rent again."
United States
Joan T.
Soulas Martha's Vineyard, Walk to Inkwell Beach & Town
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

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