 He married Barbara Elizabeth Errington on 30 December 1915, and on 9 Nov 1916 had a daughter, Roshnara Barbara Wingfield-Stratford (who married and later divorced Richard John Wrottesley, 5th Baron Wrottesley)

Wingfield-Stratford's first substantial work was "The History of English Patriotism" (2 vols., 1913), a theme to which he several times returned.The most lasting of his books remains "The History of British Civilization" (2 vols., 1928) which stands comparison with the better-known one-volume histories of England by G. M. Trevelyan and Keith Feiling.Trevelyan (thanked in the preface along with Eileen Power) was one of a number of professional historians, which also included R. H. Tawney and John and Barbara Hammond, who were his neighbours in the country and provided companions for long walks during which historical issues provided the staple of conversation.