Winifred Watson lived her life in Newcastle upon Tyne. Although she was expected to attend university, as had her sisters, she was unable due to the Depression and its impact on her father's business. She began working as a typist to help support the family. Winifred once said "The person I worked for never gave me any work until the afternoon -- he told me to bring some knitting in. So I wrote the whole book in the office." Fell Top was written in part as a result of a dare from her brother-in-law after she remarked that what she was reading was rubbish and could do better herself. After finishing Fell Top, she put the manuscript away and did not attempt to publish until years later when her sister saw an advertisement from a publisher. The publisher accepted Fell Top which was published in 1935, and asked if there were any more manuscripts. Reviewers were impressed with Fell Top and it was adapted into a BBC radio play. (Fell Top was the kind of rustic novel that Stella Gibbons caricatured in her novel, Cold Comfort Farm.) Her second novel, Odd Shoes was published in 1936.

With the exception of Miss Pettigrew, all of Watson's novels are set in the countryside. Miss Pettigrew Lives For A Day, was Watson's third novel and was initially rejected. Watson had wanted to write a fun story after her work on two dramas. She and her publisher compromised and she agreed to write another drama set in the country similar to her previous work if they would publish Miss Pettigrew Lives for a Day. Upyonder was published in 1938. As Ms. Watson predicted, Miss Pettigrew was an immediate success...in England, Australia and the United States. It was translated and published in France, and was about to be printed in Germany when World War II started. A musical film version was planned, starring Billie Burke as Miss Pettigrew, but Pearl Harbor put paid to that. "I wish the Japanese had waited six months," Watson said 60 years later.

Watson married Leslie Pickering, manager of a local timber firm, in January 1936. Once married, she wrote every day. She published her sixth and final novel, Leave and Bequeath, in 1943 when she was 37. She had a son, Keith, who survived the Blitz by pure chance. Watson had put him upstairs but he was fussy so she brought him downstairs. A bomb destroyed the house next door and the fireplace was blown onto his cot. Being downstairs, he survived. Sometimes she said she had written all she wanted to write. Other times, however, she stated it was her circumstances that made it impossible to write. During the Blitz, she and her mother and the family next door moved in with Watson's in-laws: "I just quit. It became impossible to write in a strange house with only one room for us all and my mother living with us, too. All my creative energy went into Keith."

Persephone Books published Miss Pettigrew Lives For A Day first in 2001, then in 2003, 2004, and 2005, and finally as a Persephone Classic in 2008 with a preface by Henrietta Twycross-Martin.

She died in Newcastle upon Tyne on August 5, 2002. The film version of Miss Pettigrew Lives for a Day was released in 2008 with Frances McDormand in the lead role and Amy Adams as Delysia LaFosse.