In 1661, Winston became Member of Parliament for Weymouth, and as a mark of royal favour he received rewards for losses incurred fighting against the Parliamentarians during the civil war, including the appointment as a Commissioner for Irish Land Claims in Dublin in 1661.
I 1661 blev Winston medlem af parlamentet for Weymouth, og som et tegn på kongelig gunst fik han også belønninger for tab, han havde lidt under kampen mod parlamentet under borgerkrigen, herunder en udnævnelse til kommissær for irske jordrettigheder i Dublin i 1662.