Berkhamsted Castle was taken prisoner at the Battle of Poitiers. When the Black Prince fell ill following his campaigning in France, he retired to Berkhamsted and died there in 1376. Richard II inherited Berkamsted Castle in 1377; initially the use of it was given to his favourite, Robert de Vere and, after de Vere's fall from power and exile in 1388, to John Holland. Henry IV lived in the castle after he deposed Richard in 1400, and he used the property to detain rival applicants to the throne. During this period Geoffrey Chaucer, later famous for his "Canterbury Tales", oversaw renovation work
Clan Ramsay was claimed by the Douglases who became jealous and William Douglas, Lord of Liddesdale captured Alexander Ramsay with a strong force of men, imprisoning him in Hermitage Castle, where he was starved to death. Alexander's brother, William Ramsay, was captured by the English at the Battle of Neville's Cross but was not killed by them as he lived to tell the tale. In 1400 another Sir Alexander Ramsay held out in Dalhousie Castle against a siege by the English, who were forced to retreat due to Ramsay's resolute resistance. In 1513 during the Anglo-Scottish Wars, Sir Alexander's descendant, another Alexander