Book Kid-Friendly Hotels in Chestertown from $652

Name: Friends Lake Inn
Rating: 8.6

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Top Chestertown Kid Friendly Hotels

The Fern Lodge

46 Fiddlehead Bay Rd. Chestertown NY

$587 nightly

$652 total

Jan 6 - Jan 7, 2026

Total with taxes and fees

This bed & breakfast's 8 hot tubs and gym are among the featured amenities. Enjoy the sauna and free perks like local cuisine breakfast and free self parking. ...

9.8/10 Exceptional! (46 reviews)

I cannot say enough good things about the Fern Lodge. Beautiful atmosphere, wonderful host. Will be returning!

Reviewed on Dec 27, 2025

Lily Pad South at Loon Lake near Gore Mountain

Chestertown NY

This apartment features a garden, laundry facilities, and barbecue grills.

9.6/10 Exceptional! (48 reviews)

Fun Week

We had a great time at the Lily Pad. Spent a day at Lake Placid and another day at Lake George...plus took in some of the sights and enjoyed the nearby beach and kayaksThe place was very nice...we would stay there again

Reviewed on Jun 28, 2025

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Pine Tree Motel & Cabins

5537 State Route 8 Chestertown NY

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a picnic area, and express check-in are also on offer.

9.2/10 Wonderful! (146 reviews)

We attended the Warrensburg Largest Garage Sale Weekend. The Motel is only 20 minutes away from the event. Located near Chestertown so you can go out to eat or grab groceries at the local Grocery Store. Motel is Dog Friendly and we did not have any issues with the Wi-Fi.

Reviewed on Oct 5, 2025

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Friends Lake Inn

963 Friends Lake Rd Chestertown NY

A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a garden, ...

8.6/10 Excellent! (102 reviews)

Staff was great. The inn is unique. Perfect!

Reviewed on Sep 7, 2025

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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.

Hotels With Pools in Chestertown

Friends Lake Inn

963 Friends Lake Rd Chestertown NY

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8.6/10 Excellent! (102 reviews)

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!