Chester is a village in Orange County, New York, United States. The population was 3,993 at the 2020 census. It was named after the City of Chester in the Cheshire region of northwest England. Chester is part of the Poughkeepsie–Newburgh–Middletown, NY Metropolitan Statistical Area as well as the larger New York–Newark–Bridgeport, NY-NJ-CT-PA Combined Statistical Area.