In 1499, Cholmeley and his younger brother Roger were appointed Constables of Pickering Castle, North Yorkshire and Stewards of the Honour and Foresters of the Royal Forest.
castle | Windsor Castle | Castle | Edinburgh Castle | Balmoral Castle | Castle (TV series) | Prague Castle | Castle Donington | Corfe Castle | Castle Hill | Castle Hill, New South Wales | Powis Castle | Roy Castle | Pickering | Colditz Castle | Castle Combe | New Castle | Nagoya Castle | Dublin Castle | New Castle, Delaware | Lancaster Castle | Hearst Castle | Harold & Kumar Go to White Castle | Cardiff Castle | The Castle of Otranto | Tantallon Castle | Takeshi's Castle | Luttrellstown Castle | Dover Castle | Buda Castle |
By 1255 he was serving as chief justice of the forests north of the Trent, and warden of Bamburgh, Pickering, and Scarborough castles.