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
Hugh Waterton of Eaton Tregoz near Ross-on-Wye in Herefordshire, which by an inquisition taken after his death was found to contain castle buildings and a deer park of 144 acres. By 1377 he was one of Gaunt's retainers, and in 1399 an executor of his will. From the late 1370s he was also associated with Gaunt's son, Henry Bolingbroke, the future Henry IV, becoming a Privy Councillor and by 1386 was Bolingbroke's chamberlain. On 10 July 1386 he was among those who gave evidence in the celebrated case between Richard le Scrope, 1st Baron Scrope of Bolton, and Sir Robert Grosvernor as