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Find Family Hotels in Chestertown, MD from CA $87

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Top Chestertown Family Hotels

Popular hotels great for families

Most favorite kid-friendly stays in Chestertown in 2024
Hotels with pools in Chestertown

Hotels with pools

Hotels with pools
Hotels with kitchenette in Chestertown

Hotels with kitchenette

Hotels with kitchenette

Chestertown Family Hotels information

 

Family Hotels in Chestertown

5

Highest price
CA $156
Cheapest price
CA $87
Number of guest reviews
822
Total number of hotels in Chestertown
997

 

Frequently asked questions

What's Chestertown like for family-friendly vacations?
If you’ve been thinking about a trip with your kids, the historic destination of Chestertown is a good choice. The boating, festivals, and wildlife are just a few things that make this an attractive vacation spot for families. Arrange a flight into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) from the city center.
What's the best place to stay when traveling with kids to 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 family trip.
How many hotels that welcome families are there in Chestertown?
Expedia has 6 family-friendly hotels and other accommodations in Chestertown.
When's the best time to book a family-friendly vacation in Chestertown?
The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.
What's there to see and do with your family in Chestertown?
While you are vacationing in Chestertown, you and the family might want to see interesting spots such as Rolphs Wharf Marina and Historical Society of Kent County Maryland. Make sure you have lots of time for activities like Garfield Center for the Arts at the Prince Theater and Crumpton Auction.

Recent Reviews in Chestertown
Expedia verified reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

5/5 Excellent
"Lovely historic Inn, excellent help, excellent valet. "
A verified traveller from Brooklyn stayed at Historic Inns of Annapolis
Posted 1 day ago
Historic Inns of Annapolis