St. Charles HotelSt. Charles Hotel

Also known as the Brawner Hotel, this was one of Port Tobacco's best known and most prosperous tavern-hotels. St. Charles Hotel was a large, two-story frame structure built over a partially elevated brick-walled cellar. In the late 18th century it was advertised as having 25 bedrooms, a dining room that seated 200, a game room, breakfast room, reception rooms, a proprietors' suite and quarters for servants.

St. Charles Hotel is another possible location where John Wilkes Booth planned his attempt to kidnap President Abraham Lincoln. James Brawner, owner of the hotel, sold a boat owned by himself and Richard Smoot to Booth. During the Civil War the hotel also saw the likes of the 8th Illinois Calvary, who were stationed in the Port Tobacco courthouse in June 1864. Extensive excavation was carried out on the St. Charles Hotel in the 1960s by local archaeology enthusiasts, but no reports, notes, or intact collections of artifacts survive from that work.