Vacation rentals in Chestertown
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Top-rated vacation rentals in Chestertown
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chestertown vacation rentals
Other great vacation rentals in Chestertown
Guest favorite
Cabin in Johnsburg
4.97 out of 5 average rating, 69 reviews2 bdrm ADK cabin 10 mins to GORE MTN
Nov 30 – Dec 7
G$31,146 GYD per night
Guest favorite
Cabin in Warrensburg
4.93 out of 5 average rating, 30 reviewsBearpine Cottage
Sep 11 – 18
G$29,110 GYD per night
Guest favorite
Vacation home in Chestertown
5.0 out of 5 average rating, 23 reviewsGreen Mansions Vacation Condo, 2 bedroom & 2 bath
Jan 4 – 11
G$29,180 GYD per night
Guest favorite
Barn in Chestertown
4.98 out of 5 average rating, 46 reviewsAdirondack Base Camp by Loon Lake and Gore Mt.!
Sep 14 – 21
G$38,536 GYD per night
Guest favorite
Home in Chestertown
4.96 out of 5 average rating, 67 reviewsModern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
May 10 – 17
G$68,923 GYD per night
Guest favorite
Cottage in Chestertown
4.93 out of 5 average rating, 14 reviewsPrivate, Loon Lake front cozy cabin on 3 Acres
Jan 27 – Feb 3
G$39,294 GYD per night
Guest favorite
Home in Minerva
4.96 out of 5 average rating, 94 reviewsCozy Central Adirondack Charmer
Jun 2 – 9
G$21,546 GYD per night
Guest favorite
Apartment in Warrensburg
4.89 out of 5 average rating, 70 reviewsCozy Adirondack Getaway
Dec 29 – Jan 5
G$21,968 GYD per night
Quick stats about vacation rentals in Chestertown
Total rentals
10 properties
Popular amenities
Kitchen, Wifi, and Pool
Wifi availability
10 properties include access to wifi
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
270 reviews
Nightly prices starting at
G$18,759 GYD before taxes and fees
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