Chestertown Vacation Packages
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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.
Top Chestertown Vacation Deals
The Queensbury Hotel
Reviewed on May 10, 2026
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 3 kilometres from the downtown area.
Chestertown Hotel Deals
Six Flags Great Escape Lodge & Indoor Waterpark
A lot of fun for the whole family. Part of the Waterpark was close which was a bummer, but overall a fun time.
Reviewed on May 11, 2026
The Queensbury Hotel
Always an amazing stay at the QUEENSBURY!!
Reviewed on May 10, 2026
Holiday Inn Resort Lake George - Adirondack Area by IHG
Phenomenal staff at every level. Beautiful room, extremely clean. Great view of the Lake. Fantastic restaurant and lounge. Plenty of activities on site.
Reviewed on May 8, 2026
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.
