The original town of Winchelsea grew up as a Saxon fishing settlement during the 11th century. It was built on a massive shingle bank that extended northeast from Fairlight Head, across what is now Rye Bay, to Lydd and beyond.
This location is at the root of Winchelsea's name. The suffix -chelsea comes from the Saxon word chesil, which refers to a shingle beach or embankment. The prefix Win- may be derived from the word gwent meaning a level and refers to the marshland behind the old town.
The historian Cooper reported the unlikely proposition that the prefix was derived from the word wind and referred to Old Winchelsea's exposed position on the coast. Other authors have favoured wincel- meaning corner (of the great shingle bank) and win- derived from market. Behind the great shingle bank on which Old Winchelsea was sited, a wide shallow bay called the Camber (from chamber) was formed by the conjoint estuaries of the Rivers Brede, Rother and Tillingham.