A stately Federal-style home (circa 1830), the Holladay House was standing during President James Madison's lifetime and is only 3 miles away from his Montpelier plantation. John Madison Chapman, grand nephew of James Madison, owned the Holladay House for most of the mid-19th century.
During the Confederate Winter encampment of 1863/64, John Madison Chapman's daughter, Emma, married Robert Boykin, a Captain in General Lee's army. According to the diary of John Samuel Apperson, a hospital steward who had pitched his tent across the street, several famous Confederate officers, including J.E.B Stuart and others, celebrated this war-time wedding in the house until 4am.
In 1899, Dr. Lewis Holladay, the inn's namesake, purchased the home and it remained in his family for over 100 years.
The Holladay House, now an historic inn welcoming guests, keeps much of its original woodwork, mantles, hardware and windows.