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.
Choose the perfect accommodation for your trip at AllTheRooms.com. We aggregate Airbnb, Homeaway, VRBO and more. Chestertown has 222 hotels, vacation rentals and other unique places to stay, with prices to suit budget travelers, luxury travelers and everything in between. For those trying to keep costs down, the lowest priced place to stay in Chestertown comes in at $25 per night. The average price of accommodation in is $286 per night.
Those looking to get some work done during their trip to Chestertown can pick from 136 places to stay that provide WiFi. We have 11 accommodations that come with a breakfast included. You can keep up with your workout regime by staying at one of 3 accommodations that provide gym facilities. Driving to Chestertown? Then choose one of the 126 places to stay that comes with a parking spot included. 5 accommodations come with a pool or jacuzzi
Those traveling with a dog, cat or some other animal can stay in one of 38 accommodations that are designated as pet-friendly.
We combine a wide variety of Chestertown accommodations including vacation rentals, homestays, hostels and other unique places to stay into one easy search. We show results from more than 5 providers, including 78 places to stay from Airbnb, 32 accommodations from Homeaway and 20 places to stay from VRBO.
140 of our accommodations in Chestertown have been reviewed and rated. 67% are rated excellent or good. 87 places to stay in are instantly bookable.