FREE HIGH SPEED INTERNET access in all rooms! Enjoy evening fresh-baked cookies, heated indoor pool, spacious suites with refrigerator, microwave,... more

With a fanciful gingerbread-trimmed triple-porch facade, this three-story brick building is a focal point along the main street of Chesterto... more

609 Washington Ave
Chestertown, MD 21620

500 Double Creek Point Rd
Chestertown, MD 21620

The new and exciting Holiday Inn Express Hotel and Suites Chestertown is located off Route 213, within walking distance to beautiful downtown Chest... more

239 High St
Chestertown, MD 21620

206 Washington Ave
Chestertown, MD 21620

108 Spring Ave
Chestertown, MD 21620

In the middle of all that Colonial grandeur sits this Victorian lady, an 1877 beauty with five guest rooms, all with king-size or queen-size... more

Washington may have had a drink at this tavern, but now you can sleep here. This 1730 inn has six comfortable Colonial guest rooms. The form... more