Book Kid-Friendly Hotels in Chestertown from $175
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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
Friends Lake Inn
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!
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Recent Chestertown Hotel Reviews By Fellow Wanderers
Holiday Inn Resort Lake George - Adirondack Area by IHG
"I was called to advise my room was ready and when we got there and received our keys we lugged our luggage to the room and immediately realized we were given the wrong room. I felt the front desk staff were very confused . My sister in law was checking in same day. They could not get it straight on who was who. I never received an apology for having to walk very far with a ton of luggage and walk back with luggage to get correct room keys. I advised them it was her room and further advised when they called me to say room was ready they asked for me by name. Then my sister in law called and asked if her room was ready they said no- when I advised them of this they said her room isn’t ready I says yes it is you just gave me her keys and they kept referring to me as her name. Then asked me to call her to tell her that her room was ready!! They ended up calling her. Needless to say besides all that-the actual hotel was very clean. The trivia was fun but the pool as well."
