
Chestertown Vacations
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Your Chestertown Vacation
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 vacation 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 vacation is only a few clicks away with Expedia.
Discover the most popular places to visit in Chestertown
Loon Lake Beach
If a restful vacation is part of your travel plans, Loon Lake Beach might be the perfect place to seek out during your trip to Chestertown. While you're in the area, stroll along the lakeside.
Chestertown Hotel Deals

Friends Lake Inn
"I was in need of a hotel room at relatively short notice for a basketball tournament that I was refereeing. I came across the Finger Lakes Inn as it was just a short drive away from where the tournament was being held. Nestled in the Adirondack, it is a pleasant and quaint place to stay. If you like ..."
Reviewed on May 18, 2026

The Queensbury Hotel
"Everything was great"
Reviewed on Jun 1, 2026

Six Flags Great Escape Lodge & Indoor Waterpark
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Reviewed on Jun 1, 2026
Find the Best Chestertown Vacation Packages
Chestertown Beach Vacation
Escape the stresses of daily life and let your body, mind and soul completely relax during your Chestertown vacation. Few things are more invigorating than the cool sea breeze and the soothing sound of waves lapping at the shore. Organize your trip to Chestertown the quick and easy way by locking in one of our Chestertown vacation deals. Many visitors opt to base themselves near Loon Lake Beach, a must-see only 2 miles (3 km) from the downtown area.
Chestertown Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 680 |
Max Temp Winter | 30ºF |
Max Temp Summer | 75ºF |
Top Sights | Gore Mountain Ski Resort, Loon Lake Beach and Natural Stone Bridge and Caves |



















