The History of the Holladay House Bed and Breakfast in Orange, VA

Holladay House Bed and Breakfast, circa 1895


Holladay House Historic District    Soldier of Faith by Mort Kunstler        Portrait of Dr. Lewis Holladay, ca. 1940    An Historic Bed and Breakfast in Virginia
1830-1849  1849-1883  1883-1899  1899-1989    1989-Present


Built circa 1830, the Holladay House Bed and Breakfast in Orange, Virginia has witnessed almost 180 years of American history, and is on the nationally-recognized Journey Through Hallowed Ground. The namesake of this charming bed and breakfast is Dr. Lewis Holladay, who purchased the home in 1899 and operated his medical practice here. Now a Virginia Bed and Breakfast inn, the Holladay House is one of the two oldest standing structures in historic downtown Orange, VA, and is registered with the National Register of Historic Places as a property that contributes to the Orange Downtown Commercial Historic District. In the the photo above, taken around 1895, the Holladay House is the first house on the left.

At the intersection of historic Routes 15 and 20 (James Madison Highway and Constitution Highway), the Holladay House is situated at an important crossroads in American history. Three miles to the west, James Madison, the author of the U.S. Constitution, made his home with Dolley Madison (the first “first lady”) at James Madison’s Montpelier. Numerous historical circumstances and architectural similarities connect these two properties. The Holladay House property is the only present-day inn in Orange County that was standing during the lifetime of President James Madison, and the house shares many of the same architectural elements as James Madison’s Montpelier. In addition, one of the early owners of the Holladay House was John Madison Chapman, a grand-nephew of President James Madison. The Holladay House connections to Montpelier continue even into the 20th century. During World War I, the duPont family established a hospital for convalescing soldiers on the Montpelier property, and Dr. Holladay attended them there.

Painting of the Holladay House by Linda Boudreaux Montgomery            Water color of James Madison's Montpelier, painted ca. 1830
Painting of the Holladay House by Linda Boudreaux Montgomery
Ca. 1830 water color depicting James Madison’s Montpelier at the time the Holladay House was built.


 The famous Brigadier General
J.E.B Stuart attended a wedding
reception at the Chapman’s
home, now a bed and breakfast
in Orange, VA.

The Holladay House also contributed to local Civil War history. As Virginia’s commemoration of the American Civil War Sesquicentennial attests, Orange County played a pivotal role for both the North and the South during the Civil War. During this painful time in the American historical narrative, the Holladay House witnessed and hosted events and personalities that were important to the conduct of the war.

In 1862, open war exploded in front of the house as Union and Confederate cavalry soldiers skirmished up and down Main Street, killing between 20 and 50 Americans. An unverified local legend tells that a Confederate soldier died on the Holladay House’s front steps. A year later, during the winter of 1863/64, Robert E. Lee’s army took refuge in Orange after its bitter defeat at Gettysburg. As a prominent house on the Main Street of Orange, important Confederate leaders such as Robert E. Lee, J.E.B Stuart, A.P. Hill, and Jefferson Davis passed by its doors as they conducted the administration of war. 

In February 1864, the Chapman family hosted a wedding reception for their daughter and her new husband, an officer in Robert E. Lee’s army. Attendees included a number of high-ranking Confederates, including the charismatic Brigadier General J.E.B. Stuart. One block away, the St. Thomas Episcopal Church (where Robert E. Lee worshipped while headquartered in Orange) became a temporary hospital for wounded soldiers after the battles of Cedar Mountain, Chancellorsville, the Wilderness, and Spotsylvania Court House.

This colorful historic tradition of the Holladay House and the Town of Orange continues today. Throughout the last two centuries, the Holladay House has served the citizens of Orange, Virginia as a residence, a law office, a doctor’s office, a dentist’s office, and a Virginia Bed and Breakfast inn. In the early 20th century, a private schoolhouse for local children was on the property. Only a handful of proprietors have owned this historic home, and the Holladay family was its steward for over 100 years. This historic bed and breakfast still boasts much of its original woodwork, including floors, mantels, doors and period antiques from the Holladay family. The current owners, Samuel and Sharon Elswick, consider themselves to be stewards of this Virginia Bed and Breakfast’s rich history, and are anxious to share the experiences of those that came before with the diverse guests that visit the inn each day!

Follow the links below for more historical information!

1830 - 1849: Construction and Early Residents

1849 - 1883: The Chapman Family and the American Civil War

1883 - 1899: MacDonald Family and the Methodist Parsonage

1899 - 1989: The Holladay Family

1989 - Present: Holladay House Bed and Breakfast

For information about local historical sites and heritage tourism, see our Travel Guide for Charlottesville, Orange, and Central Virginia.

To begin an adventure into history, visit our Virginia Travel Packages page, which includes special packages and itineraries for Heritage Tourism, Archaeology Travel, Civil War Sesquicentennial Events, and Civil War Tours.