Best Family Friendly Hotels in Chestertown (MD) (Updated June 2026)
Welcome to Chestertown, Maryland! A charming destination nestled on the banks of the Chester River on Maryland's Eastern Shore. This quaint town is a treasure trove of history, culture, and outdoor adventures - a perfect getaway for young travelers aged 18 and above.
With its rich Colonial and Victorian architecture, Chestertown paints a picture of a bygone era. Its vibrant arts scene, bustling farmers market, and unique local shops offer a delightful mix of old and new.
For nature enthusiasts, the town's scenic river and trails offer a multitude of activities, from kayaking to bird-watching. Foodies can indulge in the freshest seafood and local produce at the many farm-to-table restaurants. Whether you're in for a weekend escape or a longer stay, Chestertown promises an experience filled with discovery and relaxation.
Below is a list of the best family friendly hotels in Chestertown. Whether you want a hotel with a pool, kids' activities, spacious suites, or convenient access to attractions, you'll find options for every family and budget!
Hotel amenities and family policies may change at any time. We recommend confirming family friendly features directly with the hotel before booking.
Top Family Friendly Hotels in Chestertown
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Comfort Inn & Suites Chestertown150 Scheeler Road, Chestertown, 21620 -
Driftwood Inn609 Washington Avenue, Chestertown, 21620
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Red Roof Inn & Suites Chestertown160 Scheeler Rd, Chestertown, 21620
Look for hotels with amenities like spacious rooms, cribs, kids' clubs, pools, playgrounds, and family dining. Read reviews from other families and check the hotel's website for up-to-date information on services and policies.