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Vacation rentals in Chestertown
Find and book unique accommodations on Airbnb
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
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Guest favorite
Home in Chestertown
5 out of 5 average rating, 21 reviewsBlue Bay Retreat - Loon Lake Lakefront w/ Hot Tub
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Guest favorite
Guesthouse in Bolton Landing
4.96 out of 5 average rating, 89 reviewsBolton Landing - Cozy Adirondack Cabin Home
![](https://a0.muscache.com/im/pictures/hosting/Hosting-44551946/original/78792ee8-1510-46ea-ac0d-40ba5893f1e0.jpeg?im_w=720)
Guest favorite
Cabin in Chestertown
4.99 out of 5 average rating, 75 reviewsPosh Camp the Quintessential Adirondack Cabin
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Guest favorite
Cabin in Chestertown
5 out of 5 average rating, 8 reviewsThe Charming Loon
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Guest favorite
Home in Chestertown
4.96 out of 5 average rating, 27 reviewsADK Spacious Home! Huge yard, campfire, games, AC
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Guest favorite
Guesthouse in North Creek
5 out of 5 average rating, 61 reviewsWelcome to a Private Chalet w/ a home feeling!
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Guest favorite
Cabin in Warrensburg
4.95 out of 5 average rating, 44 reviewsBearpine Cottage
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Guest favorite
Home in Chestertown
5 out of 5 average rating, 17 reviewsThe Hayes Homestead
Quick stats about vacation rentals in Chestertown
Total rentals
10 properties
Nightly prices starting at
$90 before taxes and fees
Total number of reviews
280 reviews
Family-friendly rentals
10 properties are a good fit for families
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
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