Chestertown Holidays
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Your Chestertown Holiday
There's plenty to like about Chestertown, from its rich history to its spectacular views and beyond. When you're ready to spend a bit of time in this fascinating city, our Chestertown holiday packages will be just the thing. You'll want to sightsee during your trip to Chestertown. Carve out some time for leading attractions such as Friends Lake, Loon Lake and Loon Lake Beach. Your dream Chestertown holiday is clicks away. Browse airfares, hotels and more on Expedia for a getaway that's tailored just for you.
Chestertown Holiday
Chestertown Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 680 |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 24ºC |
Top Sights | Gore Mountain Ski Resort, Loon Lake Beach and Natural Stone Bridge and Caves |
Our pick of the best Chestertown Hotel Deals
Pine Tree Motel & Cabins
5537 State Route 8 Chestertown NY
9.2/10 Wonderful! (146 reviews)
We attended the Warrensburg Largest Garage Sale Weekend. The Motel is only 20 minutes away from the event. Located near Chestertown so you can go out to eat or grab groceries at the local Grocery Store. Motel is Dog Friendly and we did not have any issues with the Wi-Fi.
Reviewed on 5 Oct 2025
Friends Lake Inn
963 Friends Lake Rd Chestertown NY
8.6/10 Excellent! (102 reviews)
Staff was great. The inn is unique. Perfect!
Reviewed on 7 Sept 2025
The Fern Lodge
46 Fiddlehead Bay Rd. Chestertown NY
9.8/10 Exceptional! (45 reviews)
Absolutely beautiful
Reviewed on 22 Oct 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
