Winterset can refer to:
- Winterset, Iowa, a city in Madison County, Iowa
- Winterset City Park, a public, city-owned park in Winterset, Iowa
- Winterset Township, Russell County, Kansas (population: 67)
- Winterset (play), a play by Maxwell Anderson
- Winterset (film), a 1936 film adaptation of the play
- Winterset Award, a Newfoundland and Labrador literary award
- Rachel Unthank and the Winterset, a British folk music group