Chestertown Holidays
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Your Chestertown Holiday
There's plenty to like about Chestertown, from its rich history to its spectacular views. When you're ready to spend a bit of time in this interesting city, our Chestertown holiday packages will be ideal for you. Friends Lake, Loon Lake and Loon Lake Beach are just a few of the sights you'll want to see during your trip to Chestertown. Don't put off your visit to this destination any longer. Your dream Chestertown holiday is only a few clicks away with Expedia.
Chestertown Beach Holiday
Escape the stresses of daily life and let your body, mind and soul completely relax during your Chestertown holiday. Few things are more invigorating than the cool sea breeze and the soothing sound of waves lapping at the shore. Organise your trip to Chestertown the quick and easy way by locking in one of our Chestertown holiday deals. Many visitors opt to base themselves near Loon Lake Beach, a must-see only 2 miles from the downtown area.
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 |
Top hotels in Chestertown
The Fern Lodge
I cannot say enough good things about the Fern Lodge. Beautiful atmosphere, wonderful host. Will be returning!
Reviewed on 27 Dec 2025
Elizabeth. A Guest House Near Lake George.
The house was beautiful and charming and plenty of space. We have no complaints but recommend hand towels in the bathrooms. Probably will look up this place again for a skiing trip this winter.
Reviewed on 10 Aug 2025
Eagles Nest at Loon Lake near Gore Mountain
Great house. Great location
Reviewed on 4 Jan 2026
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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. Flight-inclusive packages are ATOL protected.
