Built in 1899 on the site of a former inn which was destroyed by fire in 1896, by the architects Veall and Sant of Cardiff, (who were responsible for some of Cardiff's best schools). The old inn was built c.1610 by Margaret Cleyston who owned Gate House and was run by her as an inn until her death in 1626.

A three storey hotel in a simplified 17th century style built of coursed, rock-faced stone with ashlar dressings and brick decorative banding with rubbed brick relief panels. It has a slate roof with a deep moulded eaves cornice and tall corniced brick stacks. It has a wide frontage, being a 15-window range in all, grouped into 4 bays. The ground floor has cross windows with mullions and transoms within an ashlar surround, and the upper two storeys have horned sashes and multipane upper lights. The main entrance is to the centre right, and has a doorway with a moulded Tudor-arch, and a leaded overlight to recessed, double, 6-panelled, part-glazed doors. Above, is a small, heavily moulded balcony on wide brackets with quatrefoil decoration, which is in front of the double light, first floor, window. There is a brick and stone plinth. On the downhill side to the left is the pedestrian link with the High Street which was created in the early 20th century.

Internally the lobby has an inner glazed door with a 6-panelled overlight containing decorative leading. The interior retains some heavy mouldings, including dado rails, door surrounds and a staircase with heavy newel posts.
(Source; Cadw listing database) S Fielding RCAHMW 20/12/2006

During the cycling craze of the 1880s and 1890s, the George Hotel was the headquarters of the Chepstow branch of the Cyclists Touring Club. It was also the headquarters of Chepstow Hockey Club.

Daryl Leeworthy, RCAHMW, 24 March 2011.