Photo by Julie Miller

Search Resorts in Chestertown

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Check prices for these dates

Next weekend
9 Jum. I - 11 Jum. I
In two weeks
16 Jum. I - 18 Jum. I
In one month
30 Jum. I - 1 Jum. II
In two months
27 Jum. II - 29 Jum. II

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

Six Flags Great Escape Lodge & Indoor Waterpark
Water park

Six Flags Great Escape Lodge & Indoor Waterpark

3.5 star property
7.8 out of 10, Good, (1105)
"Will visit again. "
The price is SAR 379
SAR 421 total
includes taxes & fees
19 May - 20 May
Six Flags Great Escape Lodge & Indoor Waterpark
Fort William Henry Hotel and Conference Center
Lake

Fort William Henry Hotel and Conference Center

3.0 star property
8.4 out of 10, Very Good, (1002)
"Outstanding accommodations and service."
The price is SAR 368
SAR 465 total
includes taxes & fees
11 May - 12 May
Fort William Henry Hotel and Conference Center
Lake George 5 Bed/ 3 Bath home w/ lake & resort access
Outdoor pool

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

9.6 out of 10, Exceptional, (7)
"We had a wonderful stay at this house on Lake George. The resort is well maintained with a lot of great features including two pools! Was a great price for a great house!"
Lake George 5 Bed/ 3 Bath home w/ lake & resort access
Mohican Resort Motel - Townhome, 2 Bedrooms
Terrace/patio

Mohican Resort Motel - Townhome, 2 Bedrooms

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

Mohican Resort Motel - 2 Bedroom Efficiency

Mohican Resort Motel - 2 Bedroom Efficiency
Mohican Resort Motel - 2 Bedroom Efficiency
Pool

Mohican Resort Motel - 2 Bedroom Efficiency

Mohican Resort Motel - 2 Bedroom Efficiency
Cozy 2 Bedroom Cottage
Outdoor pool, a heated pool

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

Trout House Village Resort
Luxury Cabin, 1 Bedroom, Lake View | Living area | 42-inch Smart TV with digital channels, DVD player, streaming services

Trout House Village Resort

3.0 star property
10.0 out of 10, Exceptional, (11)
"Absolutely wonderful place and super friendly staff "
The price is SAR 542
SAR 696 total
includes taxes & fees
5 May - 6 May
Trout House Village Resort
Walk to Million Dollar Beach from this awesome Cottage!
Exterior

Walk to Million Dollar Beach from this awesome Cottage!

10.0 out of 10, Exceptional, (151)
"Had a great time good location and plenty of room."
Walk to Million Dollar Beach from this awesome Cottage!
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS
Interior

ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS

10.0 out of 10, Exceptional, (82)
"Amazing"
The price is SAR 581
SAR 858 total
includes taxes & fees
5 May - 6 May
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS
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.