Guy's Cliffe has been occupied since Saxon times and derives its name from the legendary Guy of Warwick. Guy is supposed to have retired to a hermitage on this site, this legend led to the founding of a chantry in 1423 and the rock-carved stables and storehouses still remain.

The house has had many uses and notably a hospital during World War I and in the World War II became a school for evacuated children. Guy's Cliffe estate was broken up and sold in 1947. The new owner of the house intended to convert it into a hotel, but these plans came to nothing and the house fell into disrepair. The steady and sad decline of this historic site is now the romantic partial ruin we see today.