The George was established in about 1620 by Margaret Cleyton, the owner of the adjoining Gate House and many other properties in the area.

During the English Civil War, several military officers staying at the inn were killed in their rooms by intruders in separate incidents.

[1] In later centuries the George became a centre of Chepstow's social and community life, with inquests and petty sessions sometimes being held there.

In the late eighteenth and early nineteenth centuries, it became one of Chepstow's main coaching inns and a popular base for tourists on the "Wye Tour".

"In May 1896, the daughter of the landlord, Joseph Collins, discovered a fire in the building, apparently originating in a room behind the bar.

Rebuilding of the hotel was delayed by Watkins' death in 1897, but was completed in 1899 by the Cardiff architects Veall and Sant, with a frontage described by architectural historian John Newman as "stark neo-Tudor".