Best Chestertown (MD) Hotels With 18+ Check-In (Updated August 2025)

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 hotels and motels in Chestertown that allow reservations for guests under 21, including those aged 18, 19, and 20. From cheap options to more adult-focused accommodations, there's a variety of places to rent that fit your needs and preferences!

Please note that hotel policies regarding the minimum check-in age in Chestertown can change at any time. While we aim to keep our information updated, we recommend confirming the minimum age requirement with the hotel or motel before making a reservation.