Welcome to the Holiday Inn Express & Suites Hotel in Chestertown, Maryland near Washington College. Our hotel provides comfortable hotel rooms in Chestertown, Maryland. Our Chestertown hotel is located near several Chestertown attractions including the Hopkins Game Farm, Rock Hall with its many marinas, shops and restaurants, Goose Valley Farms, Crumpton Auctions, and the Sultana Project. Guests can further enjoy their Chestertown vacation by taking advantage of the one-of-a-kind shopping experience historic downtown Chestertown offers. Downtown Chestertown, just minutes from our hotel, houses several locally owned and operated stores. Conveniently located near the Chester River, guests of our hotel in Chestertown, Maryland, can enjoy Maryland's picturesque Mid-Atlantic scenery while paddling or riding down the Chester River. Visitors can also take walking tours of historic Chestertown, MD, discover Chestertown's rich maritime history or take daytime or sunset sailing tours. Unlike other Chestertown hotels, the Holiday Inn Express & Suites Hotel in Chestertown, Maryland, offers comfortable rooms and is conveniently located near Washington College. During your Chestertown visit, enjoy our hotel's signature Express Start hot breakfast bar (a breakfast bag to go currently during Covid) along with other amenities such as high-speed and wireless Internet access. Make your reservations at our hotel today.