Criccieth Castle a distant relation of Llywelyn ap Gruffudd, began an uprising against English rule that spread quickly through Wales. Several English-held towns were razed and Criccieth (along with Harlech Castle and Aberystwyth Castle) were besieged that winter. Its residents survived until spring when the castle was resupplied. In the 14th century the castle had a notable Welsh constable called Hywel ap Gruffydd, known as Howell the Axe, who fought for Edward III at the Battle of Poitiers in 1356. The castle was used as a prison until 1404 when Welsh forces captured the castle during the rebellion of Owain Glyndŵr. The
Owain Glyndwr Hotel dates from this time. It was supposedly the site of the first public Welsh Eisteddfod in 1789. The hotel building was enlarged with an extra wing and re-roofed about 1890. The inn is said to be haunted by the ghost of a young woman who had an affair with a local clergyman which outraged the locals. The exterior walls of the two-storey main building are painted, coursed and square stone. The hipped slate roof has three gabled dormers and red-tiled decorative cresting with finials. The later wing has a similar roof, albeit with two paired sets of dormers on either