Cooling Castle was built in the 1380s by John Cobham on the edge of marshes at Cooling, six miles north of Rochester, Kent. It is now about two miles inland. It was besieged by Thomas Wyatt the younger during Wyatt's rebellion in 1554; Lord Cobham surrendered after a brief resistance. Though he claimed to have surrendered to superior force, he had previously sympathized with Wyatt's cause, and he was briefly imprisoned for his role in the affair. The castle has also been the property of the Lollard leader John Oldcastle – executed for his beliefs, and later the source for Shakespeare's Falstaff – through his marriage to Joan Oldcastell, 4th Baroness Cobham.
During the 1990s, the property was owned by the Rochester bridge wardens. The more recent residential parts of the castle are still in use – as of 2006 it is owned by musician Jools Holland.[1] The main part of the castle is in ruins with a private house inside.[1] The gatehouse is in good condition and can be seen from the road. The barns at Cooling Castle are mainly used for weddings and civil events.
The castle was put on the English Heritage "Heritage at Risk" register in 2009.[1]