The oldest part of the Feathers, including the world-famous timber façade, was built in 1619 (during the reign of King James I) by Rees Jones, a successful attorney in the town, who had frequently appeared before the Council of the Marches, which from 1536 until 1689 was situated in Ludlow, making the town in effect the capital of Wales.

The name of the hotel springs from the motifs of ostrich feathers forming part of the timber framed façade. They can still be seen by the discerning eye on the collars of the three street gables, although now weathered by the centuries. Ostrich feathers (traditionally the badge of the Prince of Wales) were still very much in vogue in the town at the time that the timber façade was being constructed following celebrations in 1616 for the investiture of Charles (the future King Charles I) as Prince of Wales.

Ludlow was a town with Royalist sympathies and remained loyal throughout the English Civil War, during which it is thought that Royalist soldiers were billeted at the Feathers. Indeed Rees Jones' son Thomas Jones fought as a Captain in the King's Army and well after the Civil War he converted the Feathers to an inn, around 1670.

The Feathers remained an inn for the next 200 years during which time, as well as providing sleeping accommodation, food and much beer, the inn was occasionally used as a venue for cock-fighting and prize-fighting. It was also at the centre of politics in the town when candidates for parliamentary elections would make speeches from the hotel balcony then invite voters inside for a drink to help secure their votes.

From 1863 the Feathers became known as a hotel and since then has gradually evolved and expanded through the acquisition of properties on either side of the original house to become established as Ludlow's leading hotel with a fine international reputation.