Book Kid-Friendly Hotels in Chestertown from $159
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Top Chestertown Kid Friendly Hotels
Lily Pad South at Loon Lake near Gore Mountain
"The apartment was clean and comfortable!"
Reviewed on Jul 4, 2026
The Fern Lodge
"The Fern is a beautiful B&B on the Lake. We stayed in the Oak room and the view was spectacular. I highly recommend the Fern if you are looking for a quiet romantic getaway."
Reviewed on Aug 3, 2026
Pine Tree Motel & Cabins
"Really clean. Very quaint. Lovely owners. Close to “town” and close to lake. Perfect for our purposes."
Reviewed on Aug 23, 2026
Friends Lake Inn
"The staff was amazing and the restaurant was fantastic the little bit we got to try it. Unfortunately, the restaurant was closed two of the three days we were there however the nightly price increased each day. The grounds are in need of some TLC however the room was clean and comfortable. I think ..."
Reviewed on Aug 20, 2026
Hotels With Pools in Chestertown
Friends Lake Inn
Chestertown Kid-Friendly Hotels
It’s not a family vacation if you can’t bring the entire clan with you, is it? Next time you have a few days off from work, plan a family-friendly getaway. Set off on an adventure the entire family will love, and book your stay at one of the kid-friendly hotels in Chestertown.
Your little ones are the most important thing in your life, so make sure they enjoy your accommodation as much as you do. From a kids-only room service menu (macaroni and cheese, anyone?) to special perks like in-room video game consoles, these lodgings provide a little something extra for the smaller members of your crew. The best family-friendly hotels in Chestertown may even offer playgrounds and other activities to keep the kiddos busy. What’s more, some hotels provide a babysitting service so you can get a few hours to yourself!
Whether you’re traveling with one small child or hauling around your entire extended family, Travelocity is here to help. Let us hook you up with hotels for kids in Chestertown that will keep your youngsters happy without breaking the bank. You can save even more when you bundle your flight and hotel together, so what are you waiting for? Grab your family and get ready to explore!
Package deals, things to do & more in Chestertown
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Recent Chestertown Hotel Reviews By Fellow Wanderers
Baymont by Wyndham Queensbury / Lake George
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