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
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 18 Resorts in Chestertown with updated reviews, rates, and availability.

Six Flags Lodge & Indoor Waterpark

3.5 star property
7.8 out of 10, Good, (1047)
"The indoor waterpark is great! We had lots of fun with the kids. "
The price is SAR 459
SAR 676 total
includes taxes & fees
26 Jan - 27 Jan
Six Flags Lodge & Indoor Waterpark

Fort William Henry Hotel and Conference Center

3.0 star property
8.2 out of 10, Very Good, (1004)
"Good stuff"
The price is SAR 451
SAR 557 total
includes taxes & fees
19 Jan - 20 Jan
Fort William Henry Hotel and Conference Center

Lake George 5 Bed/ 3 Bath home w/ lake & resort access

9.6 out of 10, Exceptional, (7)
"This house was perfect for our group of 8 adults in town for a long weekend. There was plenty of room for us and more if we wanted. House was clean, listing was accurate and location was perfect. Todd was very helpful with our many questions. Will book again for next year."
Lake George 5 Bed/ 3 Bath home w/ lake & resort access

Mohican Resort Motel - Townhome, 2 Bedrooms

Mohican Resort Motel - Townhome, 2 Bedrooms

Cozy 2 Bedroom Cottage

Cozy 2 Bedroom Cottage

Mohican Resort Motel - Townhome, 2 Bedrooms

Mohican Resort Motel - Townhome, 2 Bedrooms

Mohican Resort Motel - 2 Bedroom Efficiency

The price is SAR 582
SAR 664 total
includes taxes & fees
31 Jan - 1 Feb
Mohican Resort Motel - 2 Bedroom Efficiency

Mohican Resort Motel - 2 Bedroom Efficiency

Mohican Resort Motel - 2 Bedroom Efficiency

Mohican Resort Motel - Townhome, 2 Bedrooms

Mohican Resort Motel - Townhome, 2 Bedrooms

Mohican Resort Motel - Townhome, 2 Bedrooms

Mohican Resort Motel - Townhome, 2 Bedrooms

Mohican Resort Motel - Townhome, 2 Bedrooms

Mohican Resort Motel - Townhome, 2 Bedrooms

Mohican Resort Motel - Townhome, 2 Bedrooms

Mohican Resort Motel - Townhome, 2 Bedrooms

Mohican Resort Motel - 2 Bedroom Efficiency

Mohican Resort Motel - 2 Bedroom Efficiency

Mohican Resort Motel - 2 Bedroom Efficiency

Mohican Resort Motel - 2 Bedroom Efficiency

Mohican Resort Motel - 2 Bedroom Efficiency

Mohican Resort Motel - 2 Bedroom Efficiency

Mohican Resort Motel - 2 Bedroom Efficiency

Mohican Resort Motel - 2 Bedroom Efficiency

Mohican Resort Motel - 2 Bedroom Efficiency

Mohican Resort Motel - 2 Bedroom Efficiency

Mohican Resort Motel - Townhome, 2 Bedrooms

Mohican Resort Motel - Townhome, 2 Bedrooms
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Chestertown
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Chestertown

Peaceful Lakeside Retreat with Private Beach

9.2 out of 10, Wonderful, (17)
"It was clean, nicely decorated, everything was new and in working order. Would suggest adding some face/wash cloths and top sheet for bed. Also, bed was comfortable but squeaked every time you made a move. All in all nice property and enjoyed our time :)"
Peaceful Lakeside Retreat with Private Beach

Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George

10.0 out of 10, Exceptional, (55)
"We could not have been happier or more comfortable in this spacious, yet cozy rental home. The property itself is so beautiful and peaceful. We used this as a home base for skiing at nearby (17 min away) Gore Mountain, and it was the perfect place to return to for an evening of relaxation by the fireplace. The hosts and property managers are lovely. "
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George

Cozy retreat with fireplace, kayaks, and shared beach/pond access

9.0 out of 10, Wonderful, (16)
"Beautiful place wood location"
Cozy retreat with fireplace, kayaks, and shared beach/pond access
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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 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, 10-minute walk from Lake George. 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.