A tiny hamlet in Warren County, Chestertown offers plenty of fun for visitors, despite it’s tiny size. Nearby are other Adirondack destinations that mean Chestertown is a popular stopping-off point.
Both Friends Lake and Loon Lake are great for swimming, cruising the waters on a boat, or hanging out on the shores with a picnic. The lakes are also particularly beautiful at sunset.
Horseback riding is a popular pastime here too, with a local family-run ranch hosting tours to explore the Adirondacks through miles of trails, forests and fields. Elsewhere, seasonal fun can be had in the nearby Dynamite Hill Park area with acres of land pefect for hiking or skiing and ice skating in winter.
After a long day exploring, check out the farmers' markets and local restaurants to savor local produce and ingredients.
Chestertown is best visited in the late spring and early summer for ideal weather to be outdoors.
Browse accommodations from all your favorite providers including Airbnb, Homeaway, VRBO and many more at AllTheRooms.com. We have 221 vacation rentals, hotels and other accommodation types in Chestertown ranging from low-cost options to luxury places to stay. A trip to Chestertown can be budget-friendly - the cheapest price accommodation is available at $40 a night. In general, a place to stay in Chestertown will cost you $287 per night.
Those needing to get some work done during their trip to Chestertown can pick from 133 places to stay that include WiFi. We have 9 accommodations that come with breakfast included. If you are driving to Chestertown, you'll want to pick from 122 places to stay that provide parking.
If you're traveling with your best friend, then make sure to choose one of the 40 pet-friendly accommodations available.
We compare vacation rentals, hotels and other unique accommodation types from loads of providers in Chestertown, including 75 places to stay from Airbnb, 32 accommodations from Homeaway and 19 places to stay from VRBO
137 of the accommodations in Chestertown have been reviewed by previous guests. They rated 68% as great. 76 places to stay in are instantly bookable.