Of an old-established Cheshire family, Cholmondeley himself was overshadowed by his father, who was, according to his monumental inscription, six times sheriff (five times of Cheshire, once of Flintshire) and vice-president of the council in the marches of Wales. In 1569, while still under age, Cholmondeley marched at the head of 130 men, raised at his father’s expense, to help suppress the rebellion in the north. His name appeared on a list of those fit to be treasurers at war in 1593, and in 1599 or 1600 he took part in a special commission with Thomas Egerton II and Thomas Sackville, Lord Buckhurst, for the suppression of schism. His main residence of Cholmondeley Hall was rebuilt about 1570 in brick and half-timber. Through his marriage Cholmondeley acquired Holford Hall, the ancient seat of the Holford family, which his wife reconstructed. He bought more property in Cheshire, and two cottages in Chancery Lane. As knight for Cheshire he was entitled to attend the subsidy committee appointed on but no activity has been found in his name in the parliamentary journals.2HMC Hatfield, v. 524; Earwaker, East Cheshire, i. 190; APC, passim.
He died at Cholmondeley in 1601 and was buried on 19 Aug. in the church at Malpas, where a richly adorned alabaster tomb was later placed over his grave. His funeral was attended by Sir Thomas Egerton.3HMC Hatfield, iv. 461; Ormerod, ii. 634; Lansd. 43, anon. jnl. f: 171; Cheshire Sheaf (ser. 3), x. 15-20; xvi. 59; xxxv. 46.