Chestertown Holidays
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- Better togetherSave up to £750 when you book a flight and hotel together*
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- Rest easyPackages with flights are ATOL protected
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 Queensbury Hotel
"I love the charm and history of the Queensberry. Walkable to many shops and restaurants in a quaint downtown. The staff is great and the on-site restaurants are amazing as well."
Reviewed on 24 Jun 2026
Six Flags Great Escape Lodge & Indoor Waterpark
"loved it. I'll definitely ho again and again"
Reviewed on 27 Jun 2026
Holiday Inn Resort Lake George - Adirondack Area by IHG
"Love this place! The kids have a great time, love their restaurant. We don't go anywhere else for Breakfast. Great amenities look no further."
Reviewed on 27 Jun 2026
Stay near popular Chestertown attractions
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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.
