Holzman has had a number of acting spots, primarily cameo roles on her own TV shows and a role as a therapist on Curb Your Enthusiasm. She also had a small role in the film Jerry Maguire. She wrote and performed several personal essays at the Un-Cabaret spoken word shows in Los Angeles and is featured on their CD Play the Word (Vol. 1).
Holzman is married to actor Paul Dooley, with whom she has one daughter, Savannah Dooley (born 1985), who is also a writer, and with whom Winnie has collaborated on various short films. Holzman and her daughter penned a TV pilot based on the Sasha Paley novel Huge, which ABC Familygreenlit in January 2010 with a direct-to-series order.Huge premiered in late June 2010. The series was cancelled on October 4, 2010 due to low ratings compared with the network's other summer hits.