Castleview Hotel

Chepstow sits on the River Wye, about 2 miles upstream of its confluence with the River Severn. The location was named Striguil (or Estrighoiel) in Norman times - from the Welsh word ystraigyl meaning a bend in the river - but by about the 14th century had become known in English as Chepstow, from the old English ceap / chepe stowe meaning market place. The Welsh name for the town, Cas-gwent (being short for Castell Gwent), means "castle of Gwent", the name Gwent itself deriving ultimately from the Roman name Venta applied to what is now called Caerwent, some 5 miles west of Chepstow.

The oldest known site of human habitation around Chepstow is at Thornwell, near the modern motorway junction, where archaeological investigations in advance of recent housing development revealed continuous human occupation from the Mesolithic period of around 5000 BC until the end of the Roman period, about 400 AD.