The Deanery is the most obvious of the survivals of the monastic buildings of the Priory of St. Swithun which was once attached to the mighty cathedral in Winchester. It was originally the house of the Prior on the edge of the 'Little Cloister' and it was here that the head of the monastery lived and entertained important guests. The domestic quarters were, in fact, largely rebuilt after becoming derelict during the Commonwealth, but the facade remains medieval in character due to the survival of the 13th century triple lancet-arch porch. Adjoining is the Prior's Great Hall, built in 1459.

It was at the Prior's House that King Henry VII's queen, Elizabeth of York, gave birth to their eldest son, Arthur, in September 1486. The lady had arrived at Winchester Castle in the hope of producing a son and heir to be named after the great British monarch who had supposedly ruled from the city so many centuries earlier. In the event though, the old stronghold was found to be much too inconvenient and the lady was moved to the Prior's luxurious apartments.

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