The castle was founded as a fortified tower house by Hugo de Gourlay before 1300, making it one of the oldest constructions of its kind in Scotland.

The de Gourlays, a Northumbrian family, supported the English in the Wars of Independence, and their land was forfeited by order of the Scottish Crown.

In July 1547, during the war of the Rough Wooing, John Lord Borthwick was made keeper of the 'place and fortalice of Halis.'

He took possession on 21 February 1548 and wrote, "the house is for the bigness of such excellent beauty within, as I have seldom seen any England except the King's Majesty's, and of very good strength.

[9] In 1567 James Hepburn, 4th Earl of Bothwell, entertained Mary, Queen of Scots, at Hailes Castle, shortly before the battle of Carberry Hill.

By the mid-19th century the castle was being used as a granary, Sir David Dalrymple, Bt., having taken advantage of the more settled times to move his family to the mansion of Newhailes.

Fifteenth century work includes a roofless chamber in which the remains of what appear to be an ambry and a piscina suggest it was a chapel rather than a hall.