Hotels with Parking in Chestertown

This 19th century estate is located on Maryland’s Eastern Shore and features lush gardens, outdoor seating, and a large wrap-around terrace with ceiling fans. Chestertown centre is 2 miles away.

Each uniquely decorated guest room at Brampton 1860 boasts an en suite bathroom with plush bathrobes and luxury toiletries. A flat-screen TV with DVD player is included.

CATHLEEN United States of America

We chose the Emory suite for our wedding anniversary, to enjoy additional comfort and it’s peaceful surroundings. The rooms were delightful and we enjoyed the convenience of the location in main building. We thoroughly loved the manor, sitting on the porch outside, listening to the rain while sampling the fine selection of teas and baked goods available to guests round the clock. The breakfast options were amazing, the charcuterie tray and Cheese boards (available for order) were delicious and satisfying, and the wine and chocolate pairing was an informative and memorable experience. We loved our mid week, anniversary getaway and we plan to return!

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Comfort Inn & Suites Chestertown is less than 1 mile from Washington College. Free Wi-Fi is available throughout the hotel.

Every room at the Comfort Inn & Suites Chestertown features a flat-screen TV, microwave, and refrigerator. They are decorated in soft colours and dark wood furnishings.

Zoraida Puerto Rico

The breakfast was excellent! All the staff was very friendly and able to answer any questions. They always had a smile!

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This motel is located just a 6-minute walk from Washington College. It offers free Wi-Fi and a 24-hour front desk. Downtown Chestertown, Maryland is 2 miles from the motel.

The Driftwood Inn has rooms decorated in rustic wood paneling and soft neutral colors. All rooms include a cable TV with HBO channels, a microwave, and refrigerator.

John United States of America

The place isn't attractive from the outside, but the condition on the inside was very surprising and nice inside. not the best place to stay but it was comfy and worth the price.

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