
Chestertown Vacations from $604
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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.
The Latest Chestertown vacation packages

Days Inn by Wyndham Queensbury/Lake George
Reviewed on Aug 18, 2025

Llama House ADK
Reviewed on Aug 10, 2025

The Alpine Lodge
Reviewed on Aug 25, 2025


Holiday Inn Express Queensbury - Lake George Area by IHG
Reviewed on Aug 11, 2025
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

Pine Tree Motel & Cabins
Reviewed on Aug 13, 2025

Friends Lake Inn
Reviewed on Aug 17, 2025

The Queensbury Hotel
Reviewed on Aug 24, 2025
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.