
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
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Popular amenities for Chestertown vacation rentals
Other great vacation rentals in Chestertown
Guest favourite

Home in Johnsburg
5 out of 5 average rating, 8 reviewsRivendell - 1st Flr: Secluded 1-bedroom w/ hot tub
Top guest favourite

Cottage in Adirondack
5 out of 5 average rating, 254 reviewsWater's Edge at Beaver Pond
Top guest favourite

Home in Chestertown
4.94 out of 5 average rating, 89 reviewsFamily friendly Adirondack dream, no cleaning fee!
Top guest favourite

Cabin in Chestertown
4.99 out of 5 average rating, 80 reviewsPosh Camp a Classic Adk Mtn. Cabin & Guide Srvc.
Guest favourite

Home in Chestertown
4.91 out of 5 average rating, 11 reviewsBase Camp
Guest favourite

Cabin in Bolton
4.91 out of 5 average rating, 57 reviewsCamp Martin
Top guest favourite

Vacation home in Chestertown
5 out of 5 average rating, 37 reviewsGreen Mansions Vacation Condo, 2 bedroom & 2 bath

Cabin in Chestertown
5 out of 5 average rating, 9 reviewsQuaint Adirondack Condo
Destinations to explore
- Plainview Vacation rentals
- New York City Vacation rentals
- Long Island Vacation rentals
- Montreal Vacation rentals
- Boston Vacation rentals
- Greater Toronto and Hamilton Area Vacation rentals
- Greater Toronto Area Vacation rentals
- East River Vacation rentals
- Mississauga Vacation rentals
- Hudson Valley Vacation rentals
- Philadelphia Vacation rentals
- Jersey Shore Vacation rentals
- Saratoga Race Course
- Six Flags Great Escape Lodge & Indoor Water park
- Gore Mountain
- Whiteface Mountain Ski Resort
- Saratoga Spa State Park
- Fort Ticonderoga
- West Mountain Ski Resort
- Pico Mountain Ski Resort
- Dorset Field Club
- National Museum of Racing and Hall of Fame
- Lake George Expedition Park
- Northern Cross Vineyard
- Autumn Mountain Winery
- Adirondack Extreme Adventure Course
- Willard Mountain
- Gooney Golf
- Lincoln Peak Vineyard
- Whaleback Vineyard