The earthworks from an 11th century motte-and-bailey castle can be seen on the high ground to the southwest of the present castle. This early castle was abandoned in the 12th century when a new castle centred on a massive stone keep was built. The keep is one of the largest in England and would have provided palatial accommodation for its time.

The timber palisades that surrounded the keep were replaced by a stone curtain wall in about 1300, and in the first half of the 15th century an extensive building programme transformed the castle into a comfortable residence with new chambers and lodgings built within the courtyard against the outer walls.

In the 15th century Middleham Castle was home to several of the greatest lords of their time, including Salisbury, Warwick and Gloucester. Richard, Duke of Gloucester, later Richard III, was particularly fond of Middleham, preferring it to any of his other castles.