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
Friends Lake Inn
"Staff was very friendly, food was excellent, room was cozy, but the property was a little disheveled. Also, no real access to the lake"
Reviewed on Aug 17, 2026
Pine Tree Motel & Cabins
Hotels With Pools in Chestertown
Friends Lake Inn
Book a stay at the best kid-friendly hotels in Chestertown
How much does it cost to stay in a family hotel in Chestertown?
You can book a stay at a kid-friendly resort in Chestertown from just $175 per night. Our prices range up $495 per night if you want to enjoy the high life.
How many family-friendly hotels are there in Chestertown?
With over 1,636 hotels in Chestertown, you have a great selection of kid-friendly places to stay. Whether you’re looking for a cheap-and-cheerful property with plenty of space or an activity-filled kid-friendly resort, there’s a getaway to suit your style and your budget at Travelocity.
What is Travelocity’s cancellation policy for family hotels in Chestertown?
We offer free cancellation on select hotels. Policies can vary per property so it's best to check before you book. If you need to amend or cancel your vacation, just visit our Customer Service Portal.
What are the best kid-friendly hotels in Chestertown?
At Travelocity, you can book the best family-friendly Chestertown hotel for you and your family by filtering your search by price, property type, and a range of amenities such as breakfast included or free airport shuttle. Use the map to see where the hotels are and the attractions they’re near.
What should I expect in the family-friendly hotels in Chestertown?
When you book a kid-friendly Chestertown resort, you can expect fun for all the family. Think pools, waterparks, and hot tubs. Think babysitting, kids’ menus, games rooms, and sport facilities—discover your ideal family vacation. Many resorts keep the kids happy, so you can indulge in bars, restaurants, and spas. Check details for each property as offers may vary.
How can I find family hotel deals in Chestertown?
Just enter your travel dates and sort your results by price. You can even filter your results by budget, so you’ll only see the deals that are right for your pocket. It’s easy to find great deals on family-friendly hotels in Chestertown with Travelocity.
When is the cheapest time to go to Chestertown with your family?
The cheapest time to visit Chestertown is usually .
When is the best time to go to Chestertown with your kids?
The most popular months are and are great for booking in at a Chestertown kid-friendly resort. If you want a quieter vacation—or the kids aren’t in school yet— are usually less busy, but you can find incredible deals all year round with Travelocity.
Why book a Chestertown child-friendly hotel with Travelocity?
Because we search the entire market, so you don’t have to. You’ll find great deals on everything from weekend trips to two-week family vacations. Whatever your budget or your wish list, we’ve got what you’re looking for.
Package deals, things to do & more in Chestertown
Fun things to do with kids in Chestertown
Best flights+hotels package deals to Chestertown
Our top All Inclusive family-friendly hotels in Chestertown
Villas, cabins and more rentals in Chestertown
Recent Chestertown Hotel Reviews By Fellow Wanderers
Adirondack Retreat Inn & Suites
"Great place to stay. Friendly staff and the pool was very warm and nice. The playground had things to do for the kids. The rooms were"
