Best Chestertown (MD) Hotels With 18+ Check-In (Updated November 2024)

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.

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Top 18+ Hotels in Chestertown

Yes, you can generally book a hotel room at 18 in Chestertown, but many hotels have a minimum check-in age of 21. Policies vary, so it's best to check the hotel's website or call directly for confirmation.

Other Hotels From Maryland You Can Check In When You're 18 Years Old

A Aberdeen Annapolis B Baltimore Barton Bowie C California Cape St. Claire Capitol Heights Catonsville Chestertown Columbia Cordova Cumberland E East New Market Easton Edgewood Elkton Ellicott City F Frederick Frostburg Fruitland G Gaithersburg Grantsville Greenbelt H Hagerstown Hancock Havre de Grace I Indian Head J Jessup K Keedysville L La Plata Largo Linthicum M Maryland City O Oakland Ocean City Odenton Oxford Oxon Hill P Pocomoke City Prince Frederick Princess Anne Q Quantico R Rosedale S Salisbury Silver Spring Snow Hill Solomons South Laurel St. Michaels Stevensville Suitland T Takoma Park Taneytown Thurmont Tilghman Island Timonium W Westminster White Marsh