Holland Cunningham was born in Roanoke, Virginia in 1967 and was educated at the University of Virginia with a BA in Art History and Studio Art. She has studied at the Art Students League, the National Academy, and the New York School of the Arts in New York City. She was a fellow at the Bau Institute in Otranto, Italy during the summer of 2012. In the Spring of 2022, she was a visiting artist at the American Academy in Rome. Her art is in numerous public and private collections all over the world. She continues to work and live in New York City and London, England.