Book Kid-Friendly Hotels in Chestertown from $70

Name: Comfort Inn & Suites Chestertown
Price range: $118 total
Rating: 8.6

Find & compare hotels, resorts and vacation rentals for the whole family

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

$106 nightly

$118 total

Jul 5 - Jul 6

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! (922 reviews)

"There are no other options in the area. We traveled a few hours for a 4 pm wedding. Arrived at 2:15. Empty parking overall and room was ready. They would not release early unless we paid $50. We had no choice as we had to get ready and could not wait until 3:00. Our son and his wife arrived at 2:30. ..."

Reviewed on Jun 13, 2026

Driftwood Inn

609 Washington Avenue Chestertown MD

Fully refundableReserve now, pay when you stay

$64 nightly

$70 total

Jun 15 - Jun 16

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 (177 reviews)

"surprisingly, this place was nice, room was semi-clean. Man at counter was nice even though his tone seemed rough but overall he was just a nice man. Bed sheets were still dirty. the bed my daughter slept on had a small blood stain on it. There was little black stuff all over the bed but besides ..."

Reviewed on May 28, 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

$106 nightly

$118 total

Jul 5 - Jul 6

Total with taxes and fees

8.6/10 Excellent! (922 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!

Package deals, things to do & more in Chestertown

Recent Chestertown Hotel Reviews By Fellow Wanderers

Hampton Inn Baltimore/Glen Burnie

5 out of 5

Posted 3 hours ago

Travelocity Verified Review

"The staff was great, our suite was clean and spacious. Everything worked, no issues. Would recommend to anyone going to Maryland with or without children. Shopping area all around hotel for convenience."

A verified traveler stayed at Hampton Inn Baltimore/Glen Burnie

Comfort Inn & Suites Chestertown

2 out of 5

Posted 21 hours ago

Travelocity Verified Review

"There are no other options in the area. We traveled a few hours for a 4 pm wedding. Arrived at 2:15. Empty parking overall and room was ready. They would not release early unless we paid $50. We had no choice as we had to get ready and could not wait until 3:00. Our son and his wife arrived at 2:30. We told them not to pay and they can get ready in our room. At 2:52, they went to the desk to see if they could get their room. They would not release a READY room unless he paid the $50. EIGHT MINUTES!! Our room had dirty stained carpet and a dirty, worn out shower. Our sons room was so smelly and musty, he had to request another. Air conditioner continuously shut off throughout the night and eventually turned back on. Avoid this place if you can."

A verified traveler stayed at Comfort Inn & Suites Chestertown

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

2 out of 5

Posted 3 days ago

Travelocity Verified Review

"The hotel is the worst hotel I have ever stayed in. The check in lady was beyond unprofessional from the first moment. Everything is super dirty and old. The only thing that was good was the breakfast. Good food and clean court. Otherwise I will never stay there again. Also charged me $25 for early checkin when the expedia email clearly stated the check in times. "

A verified traveler stayed at La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

Annapolis Waterfront Hotel, Autograph Collection

3 out of 5

Posted 3 days ago

Travelocity Verified Review

"One elevator didn’t work and the other elevator was unreliable. The restaurant is closed. The hallway and rooms feel more like a 1970’s Best Western - well worn and not without a musty odor. The HVAC in room 518 is either off or cooling the room to 65 degrees (nothing in the middle). It’s an older property and ,other than scraping it, I don’t know how you could correct all of the issues."

A verified traveler stayed at Annapolis Waterfront Hotel, Autograph Collection