The tower of Crossbasket was erected in the early 15th century and was a jointure, or dower-house of the Lindsays of Dunrod, whose principal residence was the slightly earlier Mains Castle. John Lindsay of Dunrod had been granted the lands of Kilbride by King Robert the Bruce in 1382 after the estate had been forfeited by the Comyns, who had fought against the King. Lindsay was the successor to James Lindsay, who had assisted the King in killing John III Comyn, Lord of Badenoch - also known as Red Comyn. Crossbasket remained in the hands of the Lindsays until the beginning of the 17th century, when the extravagance of Alexander of Dunrod ruined the family and caused the alienation of the estates.

By 1747, the castle was in the possession of the Peter family, who had acquired it from John Kincaid in the first decade of the 18th century. Kincaid himself had purchased the property in 1661. The most notable member of the Peter family, and resident of Crossbasket, was Thomas Peter, who was the Dean of Guild of Glasgow from 1708-9, perhaps purchasing and moving to Crossbasket after this date. A later generation of Peter was a Lieutenant-General, and it is thought that the distinctive General's Bridge of 1790 nearby was either built by or named after him.

Crossbasket House was occupied by many families during the 19th century, including Alexander Downie, John Caddell, and most famously by the inventor and raincoat manufacturer, Charles Macintosh (1766–1843). Charles Macintosh was the celebrated inventor of waterproof cloth, used in the manufacture of raincoats. Many of his experiments involved dyes; the mill on the River Calder at the rear of the house was originally constructed as a dye mill.

By 1878, ownership of the castle passed from Charles Macintosh to Alexander Downie and then John Cabbell. The latter sold the castle to Robert Clark. His son, James Clark, was a partner in the Glasgow textile and trading company James Finlay & Co. He died at Crossbasket in 1876, and his son, John Kerr Clark, continued the Clark family ownership of the castle until 1891, when it was sold to George Neilson and it was under the ownership of George Neilson that the building we recognise today was formed.

The pattern of ownership continued. The merchant Thomas Dunlop Findlay owned the property from just after World War 1 until 1932, when it was sold to James Little. James Little donated the castle to Dr Barnardo's homes around 1945. In the 1960s the James Little College was established at Crossbasket as a further education centre in Scotland. The castle was sold in 1981 to the Latter Rain Ministries, who ran the property as the Crossbasket Christian Centre until 2005. It was then sold to a developer with plans to turn the building into a series of apartments. After the developer went into administration, the building lay empty and near derelict until 2011, when it was then bought by current owners Steve and Alison Reid-Timoney, who have invested £9m into transforming it into the luxurious hotel and event venue which it is today.