Middletown is a city in Orange County, New York, USA, in New York's Hudson Valley region, near the Walkill River, in the foothills of the Shawangunk Mountains. The City of Middletown lies along the northern boundary of the New York Metropolitan Area, an imaginary line that runs from Poughkeepsie through Newburgh, Middletown, and Port Jervis, New York. The population of Middletown was 25,388 at the 2000 census. Middletown apartments for rent comparison page shows most up to date rent information on Middletown apartments and houses. Rent information is obtained from multiple rental sources but we cannot guarantee their accuracy.