Born in Faversham, Kent, the son of the Revd Roger Holloway OBE (died 2010), Holloway was educated at Cranleigh School before going to Magdalene College, Cambridge where he studied social and political sciences, graduating as MA, before postgraduate studies at Imperial College London (MBA).
Prior to his election to Parliament, Holloway was commissioned in the British Army and served with the Grenadier Guards.