Book Kid-Friendly Hotels in Chestertown from $70

Name: Comfort Inn & Suites Chestertown
Price range: $115 total
Rating: 8.6

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Top Chestertown Kid Friendly Hotels

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Chestertown MD

This vacation home featured laundry facilities and barbecue grills.

9.8/10 Exceptional! (87 reviews)

Families like: Kitchen, close to beach, sofa bed, games and toys

Travelers say...

"Great location and private setting on the river"

Reviewed on May 28, 2026

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Comfort Inn & Suites Chestertown

150 Scheeler Road Chestertown MD

Fully refundable

$104 nightly

$115 total

Sep 20 - Sep 21

Total with taxes and fees

This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will ...

8.6/10 Excellent! (966 reviews)

"Boiler went out and there was no hot water at night nor none the next morning. Half of the tv remote buttons didn’t work and 1 of the outlets in between the bed didn’t work. The front desk offered $25 for the inconveniences"

Reviewed on Aug 30, 2026

Driftwood Inn

609 Washington Avenue Chestertown MD

Fully refundableReserve now, pay when you stay

$64 nightly

$70 total

Sep 1 - Sep 2

Total with taxes and fees

Free self parking is available and the motel's front desk is staffed around-the-clock. WiFi in public areas is free. Express check-in and express check-out are ...

5.2/10 (180 reviews)

"Nice clean"

Reviewed on Aug 5, 2026

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

Comfort Inn & Suites Chestertown

150 Scheeler Road Chestertown MD

$104 nightly

$115 total

Sep 20 - Sep 21

Total with taxes and fees

8.6/10 Excellent! (966 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!