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Find Family-Friendly Hotels in Chestertown, MD

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Check availability on Chestertown Family-Friendly Hotels

Top Chestertown Family-Friendly Hotels

Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (780)
"Comfortable room, friendly staff. "
The price is £92
includes taxes & fees
17 Aug - 18 Aug
Comfort Inn & Suites Chestertown
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Terrace/patio

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

9.8 out of 10, Exceptional, (81)
"Beautiful location on the river. We were visiting family in the fall so did not use the kayaks available—maybe next time! Nice to have a dog-friendly place too. Great and prompt communication with the hosts."
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Driftwood Inn
Front of property – evening/night

Driftwood Inn

2.0 star property
5.2 out of 10, (171)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
The price is £53
includes taxes & fees
28 Jul - 29 Jul
Driftwood Inn
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.

Frequently asked questions

What's Chestertown like for family-friendly holidays?
If you've been thinking about a trip with your children, the historic destination of Chestertown is a good choice. The boating, festivals and wildlife are just a few things that make this an attractive holiday destination for families. Arrange a flight into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) from the city centre.
What's the best family accommodation in Chestertown?
Comfort Inn & Suites Chestertown is a hotel with free parking and free full breakfast, and it's a top choice on Expedia for families. Red Roof Inn & Suites Chestertown is another good option for your child-friendly holiday.
How many hotels that welcome families will I be able to find in Chestertown?
Expedia has 6 family-friendly hotels and other accommodation options in Chestertown.
When's the best time to book a family-friendly holiday in Chestertown?
The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.
What's there to see and do with your family in Chestertown?
While you are holidaying in Chestertown, you and the family may want to see some interesting spots such as Historical Society of Kent County Maryland and Rolphs Wharf Marina. Make sure that you have lots of time for activities such as Garfield Center for the Arts at the Prince Theater and Crumpton Auction.