Born in Winchester, Virginia, Holliday was the son of Dr. R.J. and Mary Catherine Taylor Holliday. He attended Winchester Academy and Yale University before earning degrees in philosophy, political economy, and law from the University of Virginia. He was the Commonwealth's Attorney for Frederick County, Virginia from 1861–65. Holliday traveled the world after his term as Governor. He died in 1899 and was buried in Mount Hebron Cemetery in Winchester, Virginia.