Photo by Julie Miller

Search Resorts in Chestertown

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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

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

Six Flags Great Escape Lodge & Indoor Waterpark
Exterior

Six Flags Great Escape Lodge & Indoor Waterpark

3.5 star property
7.8 out of 10, Good, (1064)
"We enjoyed ski and water!"
The price is AED 586
AED 813 total
includes taxes & fees
5 Mar - 6 Mar
Six Flags Great Escape Lodge & Indoor Waterpark
Fort William Henry Hotel and Conference Center
Outdoor pool

Fort William Henry Hotel and Conference Center

3.0 star property
8.4 out of 10, Very Good, (1007)
"Great hotel. Friendly staff. The food at the restaurant was great! Shout out to Marie at the restaurant for being absolutely incredible and accommodating. Marie is the BEST!! She made our stay better and would love to visit again. "
The price is AED 521
AED 634 total
includes taxes & fees
23 Feb - 24 Feb
Fort William Henry Hotel and Conference Center
Lake George 5 Bed/ 3 Bath home w/ lake & resort access
Exterior

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
Bathroom

Mohican Resort Motel - Townhome, 2 Bedrooms

Mohican Resort Motel - Townhome, 2 Bedrooms
Mohican Resort Motel - 2 Bedroom Efficiency
Bathroom

Mohican Resort Motel - 2 Bedroom Efficiency

Mohican Resort Motel - 2 Bedroom Efficiency
Mohican Resort Motel - 2 Bedroom Efficiency
Bathroom

Mohican Resort Motel - 2 Bedroom Efficiency

Mohican Resort Motel - 2 Bedroom Efficiency
Cozy 2 Bedroom Cottage
Private kitchen

Cozy 2 Bedroom Cottage

Cozy 2 Bedroom Cottage
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.
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Other property types in Chestertown

Eagles Nest at Loon Lake near Gore Mountain

Eagles Nest at Loon Lake near Gore Mountain

10.0 out of 10, Exceptional, (106)
"A fantastic location for those looking to get away in the Adirondacks. Conveniently close to Chestertown, as well as many outdoor activities, Eagles Nest was an awesome location to stay at with friends and family. "
Eagles Nest at Loon Lake near Gore Mountain
Lakefront cabin with beautiful loft, game room, views, private dock

Lakefront cabin with beautiful loft, game room, views, private dock

9.2 out of 10, Wonderful, (35)
"Loved everything from the coffee maker to the views at this place. Fantastic!"
Lakefront cabin with beautiful loft, game room, views, private dock
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
Great Room

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

10.0 out of 10, Exceptional, (57)
"Incredible place and stay, highly recommended!"
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
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 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. Amenities include 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.