Holiday Rentals in Dukes County
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Top Cities in Dukes County
Vineyard Haven
Our top choices for Dukes County holiday rentals
Apartment in Chilmark
Cozy efficiency apartment/heated pool9.6 out of 10, Exceptional, (21)
"We loved this property and would love to return!"
Clifford L.
The price is €367
includes taxes & fees
31 Dec - 1 Jan 2026
Apartment in Oak Bluffs
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View9.4 out of 10, Exceptional, (88)
"Very happy. Thank you for the stay."
Gillian S.
The price is €434
includes taxes & fees
29 Dec - 30 Dec
Holiday Home in Katama
Newly Renovated Martha's Vineyard Vacation Rental!9.6 out of 10, Exceptional, (47)
"We really enjoyed our stay. The house was conveniently located near Edgartown and South Beach in a quiet neighborhood. The house had everything we needed and more and was in great shape. Would definitely stay here again. "
Patrick S.
The price is €543
includes taxes & fees
30 Dec - 31 Dec
Holiday Home in Katama
The Seashell Cove - Martha's Vineyard9.8 out of 10, Exceptional, (24)
"Property was perfectly kept and very comfortable. "
Steve D.
The price is €500
includes taxes & fees
5 Jan - 6 Jan 2026
Holiday Home in Oak Bluffs
MOST CHIC SPOT! Your Martha's Vineyard Getaway!10.0 out of 10, Exceptional, (7)
"Our kids and their friends had so much fun in the beautifully finished basement. Easy access to beach and ferry, would love to go back every year, the host was wonderful."
Swathanthra M.
The price is €1,056
includes taxes & fees
29 Dec - 30 Dec
Holiday Home in Oak Bluffs
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!9.4 out of 10, Exceptional, (3)
"This house was perfect for our getaway. Rebecca, the host, was extremely responsive and helpful during our trip. The house was as advertised. It was clean, well equipped, and the location was perfect as well "
Louis R.
The price is €779
includes taxes & fees
29 Dec - 30 Dec
Holiday Home in Tisbury
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!10.0 out of 10, Exceptional, (16)
"The house is clean, peaceful and perfectly appointed with everything you need for a great week on the Vineyard."
Celeste P.
The price is €945
includes taxes & fees
30 Dec - 31 Dec
Apartment in Oak Bluffs
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.9.4 out of 10, Exceptional, (91)
"Great place to stay in Oak Bluffs"
Stephen S.
The price is €559
includes taxes & fees
8 Jan - 9 Jan 2026
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
Vineyard Harbor Motel - Private Beach
10/10 Excellent
Find out more about Dukes County
Holiday Homes in Dukes County
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