Born at Fyling Hall, near Whitby in Yorkshire, he was the second son of Sir Hugh Cholmeley, 1st Baronet and his wife Elizabeth Twysden, daughter of Sir William Twysden, 1st Baronet and Anne Finch.
[3] and was afterwards appointed Governor of Tangier in Morocco by King Charles II of England.
[4] From February to August 1679, he was a Member of Parliament (MP) for Northampton,[5] and from 1685 to 1687 for Thirsk.
[4] Cholmeley was described by Samuel Pepys, as a 'fine, worthy and well-disposed gentleman' with a seeming frustration for the Monarchy.
In 1663, in partnership with John Lawson and the Earl of Teviot, then governor of Tangier, he set about the building of a mole harbour, of which he became ultimately the sole contractor.