Book Kid-Friendly Hotels in Chestertown from $194

You can book a stay at a kid-friendly resort in Chestertown from just $194 per night. Our prices range up $652 per night if you want to enjoy the high life.

With over 1,545 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.

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. 

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.

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.

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. 

The cheapest time to visit Chestertown is usually .

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. 

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.