He was the son of William Huddesfield of Shillingford by his wife Alice Gold, daughter of John Gold of Seaborough and Sampit in Dorchester, MP for Dorchester in 1391, and was the grandson of William Huddesfield of Honiton, Devon.
Secondly to Katherine Courtenay, a daughter of Sir Philip Courtenay of Powderham, Devon, by his wife Elizabeth Hungerford, daughter of Walter Hungerford, 1st Baron Hungerford, and sister of Peter CourtenayBishop of Exeter and of Sir Philip Courtenay of Molland, MP and Sheriff of Devon in 1471. She requested in her will to be buried in the Greyfriars Church, Exeter "before St Francis beside the High Altar", but was probably buried at Shillingford with her husband. A monumental brass of Huddesfield and his second wife Katherine Courtenay survives in Shillingford St George Church. His sister-in-law Phillipa Courtenay married his step-son Sir Thomas Fulford, the eldest son and heir of Sir Baldwin de Fulford by his first wife Jane Bosome By his second wife Katherine Courtenay he had one daughter, according to Pole:
A monumental brass of Huddesfield and his second wife Katherine Courtenay survives in Shillingford St George Church, and the arms of Bosome survive in a stained glass window in the same church. The brass is affixed to the wall on the north side of the chancel, above a chest tomb, with grey marble slab on top, set into an Easter Sepulchre style alcove remade in the 19th century. Around the edge of the slab is an ident for an inscription in brass, now lost, but transcribed in 1630 by the Devon historian Thomas Westcote as follows:
The brass depicts a knight and a lady, both kneeling under a double canopy, with a son and two daughters. The bare headed knight is fully dressed in armour, over which he wears a tabard showing the arms of Huddesfield with a crescent for difference, with sword and spurs. in front of him is a prie dieu, on which is an open book, and his gauntlets are on the floor by his side, with his helmet on top of which is his crest, a boar rampant. The lady wears a pedimental head-dress and lappets, with gown, ornamented girdle with pomander hanging therefrom. Over all she wears a robe of estate showing the arms of Courtenay: Or, three torteaux a label of three points azure. Behind her kneels her only son by her second husband George Rogers, and behind him her two daughters Elizabeth and Katherine. The following inscription, partly in Latin, appears below :
A framed rubbing of the brass hangs in the chapel of Powderham Castle.