Photo by Julie Miller

Find Family Hotels in Chestertown, NY

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Pick from 6 Chestertown Family Hotels and compare room rates, reviews, and availability. Most hotels are fully refundable.

Lily Pad South at Loon Lake near Gore Mountain
Sledding, skiing, snowboarding at Dynamite Hill
Lily Pad South at Loon Lake near Gore Mountain
9.8 out of 10, Exceptional, (39)
"What I loved most was it was like staying in your own home, quiet, clean, and private. The only drawback was no coffee in the kitchen. Otherwise absolutely give stars. I want to stay in this exact house again if welcome. They were very nice, too, and accommodating. "
Lily Pad South at Loon Lake near Gore Mountain
The Fern Lodge
Room
The Fern Lodge
3.5 star property
9.8 out of 10, Exceptional, (42)
"Paradise just simply heavenly. And so well appointed. Feel so at home"
The price is AED 2,079
AED 2,297 total
includes taxes & fees
24 Jun - 25 Jun
The Fern Lodge
Pine Tree Motel & Cabins
Exterior
Pine Tree Motel & Cabins
2.0 star property
9.0 out of 10, Wonderful, (113)
"Cutest cabins, friendly owners, dog friendly ❤️ supporting small businesses definitely going back next year. "
The price is AED 643
AED 713 total
includes taxes & fees
24 Jun - 25 Jun
Pine Tree Motel & Cabins
Friends Lake Inn
Property entrance
Friends Lake Inn
4.0 star property
9.0 out of 10, Wonderful, (77)
"The food was made to order and very good prices were fair. The cost to stay there is overpriced."
The price is AED 1,036
AED 1,150 total
includes taxes & fees
23 Jun - 24 Jun
Friends Lake Inn
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See all available properties in Chestertown
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's Chestertown like for family-friendly vacations?
You might want to consider the remote destination of Chestertown if you’ve been thinking about a trip for the whole family. The boating, horseback riding, and canoeing are just a few things that make this an attractive vacation spot for families. Fly into Glens Falls, NY (GFL-Floyd Bennett Memorial), which is located 23.6 mi (38 km) from the city center.
How many family-friendly hotels will I be able to find in Chestertown?
Expedia has 18 hotels in Chestertown that are great for families.
When's the best time to book a family-friendly vacation 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 there to see and do with your family in Chestertown?
While you are visiting Chestertown, you and the family might want to check out some interesting spots such as Gore Mountain Ski Resort, Revolution Rail Co., and Strand Theater. Make sure you have lots of time for activities like Blue Line Outdoor Center and Up Yonda Farm Environmental Education Center.

Recent reviews of Chestertown hotels
Expedia verified reviews

Six Flags Lodge & Indoor Waterpark

Six Flags Lodge & Indoor Waterpark

5/5 Excellent
Awesome Family Get Away!
"We had an amazing time! Theme park was not packed and the hotel has its own quick entrance in. Indoor water park was cute had lots of slides for kids of all ages! We loved the arcade as it had lots of games to keep my girls busy!! "
A verified traveler stayed at Six Flags Lodge & Indoor Waterpark
Posted 11 hours ago
Six Flags Lodge & Indoor Waterpark