Photo by Julie Miller

Search Resorts in Chestertown

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
4 Apr - 6 Apr
In two weeks
11 Apr - 13 Apr
In one month
25 Apr - 27 Apr
In two months
23 May - 25 May

Compare 7 Resorts in Chestertown with updated reviews, rates, and availability.

Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Chestertown

Frequently asked questions

What can I expect from a resort vacation in Chestertown?
You deserve a vacation, and a resort is the ideal place to treat yourself to the amenities and services you need for a relaxing stay in Chestertown. One of the comfortable resorts in the surrounding area might be just what you’re looking for, whether you want great restaurants on site, shopping possibilities, or nightly entertainment options.
What's the best resort in Chestertown?
Our top-rated resorts around Chestertown: Six Flags Great Escape Lodge & Indoor Waterpark - Family-friendly resort, 10-minute walk from Six Flags Great Escape. 21.4 mi (34.5 km) from Chestertown. Has 3 restaurants, 2 bars, and a free water park. Popular for its family-friendly amenities. Fort William Henry Hotel and Conference Center - Family-friendly resort right by Fort William Henry. 16.7 mi (26.8 km) from Chestertown. Highly rated for its great location. Enjoy the 2 restaurants, seasonal outdoor pool, and sauna. Lake George 5 Bed/ 3 Bath home w/ lake & resort access - Ski resort, 5-minute walk from Lake George. 14.4 mi (23.2 km) from Chestertown. Access to ski-in/ski-out access, a water park, and an outdoor pool.
What can I do in Chestertown?
Loon Lake Beach, Friends Lake, and Loon Lake are a few of the interesting sights to visit. For more to see in the area, you can spend time at Hudson River or Tripp Pond.
What's the weather like in Chestertown?
The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chestertown are January, March, November, and December, with each month seeing an average of 13 inches of snowfall.
What's the best way to get to and around Chestertown?
Fly into Glens Falls, NY (GFL-Floyd Bennett Memorial), which is located 23.6 mi (38 km) away from the city center. If you’d like to venture out around the area, you may want to rent a car for your trip.