January in Winchester is the windiest and the coldest month of the year. In January, the weather in Winchester is typically cold. Average daily high temperature in January is about 7 degrees above zero. On average, Winchester has 20 rainy, 5 sunny, 4 cloudy, and 2 partly cloudy days in January. The rains are usually moderate. January as well as February, March, November, and December is considered the most uncomfortable time to visit Winchester.