It was built in the 1380s by the Cobham family, the local lords of the manor, to guard the area against French raids into the Thames Estuary.

The castle has an unusual layout, comprising two walled wards of unequal size next to each other, surrounded by moats and ditches.

It was captured after only eight hours when Sir Thomas Wyatt besieged it in January 1554 during his unsuccessful rebellion against Queen Mary.

In 1379, during the second phase of the Hundred Years' War, a French raid devastated towns and villages along the Thames Estuary.

"[4] Cobham fell out of the king's favour shortly after the castle was completed and he was exiled for a while, but was eventually able to return and died at Cooling in 1408.

[5] Cooling Castle saw action only once, in 1554, when it was attacked by the forces of the Kentish landowner Sir Thomas Wyatt during his rebellion against Queen Mary's engagement to King Philip II of Spain.

It is unclear why, while ostensibly marching on London, he attacked Cooling as the detour gave Mary more time to prepare her own defences.

Cobham and his son were imprisoned in the Tower of London on suspicion of having deliberately failed to defend the castle, but were soon released and allowed to return to their estates.

[1] Between 1650 and 1670, Sir Thomas Whitmore built a farmhouse within the castle's outer ward, which has undergone many alterations over the years.

An L-shaped range of outbuildings was also constructed in the outer ward, including a timber-framed barn that was built in the 17th century.

The ownership of the castle is split three ways; the barn is used as a party and wedding venue, the inner ward was owned for many years by the Rochester Bridge Wardens, and the house's current occupant is the musician Jools Holland.

It could only be accessed through an inner gatehouse halfway along the western wall of the outer ward, crossing the moat by means of a drawbridge.

[3][12] The eastern tower incorporates a copper plate on which is enamelled the following inscription, set out both in wording and in design as an imitation of a contemporary deed: Knouwyth that beth and schul be That I am mad in help of the cuntre In knowing of whyche thing Thys is chartre and wytnessyng.