Book Kid-Friendly Hotels in Chestertown from $90

Name: Comfort Inn & Suites Chestertown
Price range: $113 total
Rating: 8.4

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Top Chestertown Kid Friendly Hotels

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

Chestertown

This vacation home featured laundry facilities and barbecue grills.

9.8/10 Exceptional! (61 reviews)

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

Travelers say...

The house and hospitality exceeded all expectations! We had a wonderful long weekend away and would definitely return. The kids especially loved fishing, kayaking, and the paddle boat. The farmer’s market was enjoyable Saturday morning, too. We had beautiful weather for yard games and the fire pit. ...

Reviewed on Sep 1, 2025

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Comfort Inn & Suites Chestertown

150 Scheeler Road, Chestertown, MD

Fully refundableReserve now, pay when you stay

$102 nightly

$113 total

Oct 27 - Oct 28

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 ...

8.4/10 Very Good! (831 reviews)

The thermostat controls were easy to adjust. Night desk lady was friendly and pleasant.

Reviewed on Oct 15, 2025

Driftwood Inn

609 Washington Avenue, Chestertown, MD

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 ...

5/10 (174 reviews)

Rooms are clean, staf was helpful

Reviewed on Aug 18, 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

Comfort Inn & Suites Chestertown

150 Scheeler Road, Chestertown, MD

$102 nightly

$113 total

Oct 27 - Oct 28

Total with taxes and fees

8.4/10 Very Good! (831 reviews)

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 $90 per night. Our prices range up $113 per night if you want to enjoy the high life.

How many family-friendly hotels are there in Chestertown?

With over 1,073 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.