Holladay House: 1899-1989

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


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


The Holladay Family

Antique medical equipment from Dr. Lewis Holladay

Some of Dr. Holladay's antique medical
equipment displayed during a special
event at the Holladay House

Dr. Lewis Holladay (1868-1946) purchased the property in 1899, and it is he and his progeny that are this Virginia Bed and Breakfast’s namesake. Born on Christmas Day, 1868, Dr. Lewis Holladay was an accomplished physician, and ran his medical practice in Orange until his death in 1946. The Holladay family is an ancient and prolific Virginia family with roots reaching as far back as the early eighteenth century in Essex County. Through many generations, the Holladay family had a lengthy tradition of service in professional fields, such as lawyers, physicians, and dentists. Lewis’s grandfather, Dr. Lewis Littlepage Holladay (1803-1869), had attended the College of William and Mary (also the Innkeeper's alma mater!)  and was also a physician. He lived near Rapidan, Virginia, on a farm called “Dunlora.” Lewis Holladay’s father, Henry Thompson Holladay, owned land and a mill near Rapidan, and it was on his farm that Dr. Lewis Holladay (1868-1946) was born.

Dr. Lewis Holladay (1868-1946) married Sally Helen Price in 1892. Shortly after their first daughter was born in 1898, the Holladays moved to Orange after purchasing the McDonald’s (formerly the Chapman’s) house in 1899. At that time, only the brick portion of the house existed, and the Holladays made several additions to the building while they lived there—the two most notable in 1910 and 1917, when the frame structure on the rear of the house was completed. They also added a wrap-around porch, the front portion of which has since been removed and the façade returned to its original appearance. The side porch is still a comfortable place to enjoy a glass of Virginia wine from Orange County vineyards!


Holladay House as it appeared around 1930  Holladay House Bed and Breakfast

The Holladay House Bed and Breakfast in Orange, Virginia, circa 1930. Note what appears to be a 1930 Ford or Chevrolet Sport Coupe in the driveway, and the front porch that has since been removed.


The Holladay House Bed and Breakfast as it appears today. The Holladay House offers accommodations in Orange, VA, complete with historic suites and whirlpool suites.


Dr. Holladay served the citizens of Orange County as their physician for nearly five decades.  Educated at Hampden-Sydney College and the University of Virginia, Dr. Holladay was Dean of Physicians for Orange County throughout his medical career. In 1911, he was appointed a member of the State Board of Medical Examiners, where he served until his death. He was the Orange County Coroner and the company surgeon for the Chesapeake and Ohio Railway. In addition to his medical career, Dr. Holladay served the town as Director of the National Bank of Orange, and as the ruling elder of Orange Presbyterian Church.

Doctor Lewis Holladay Antique Sign

The original sign that was on the front of the Holladay House
in Orange, Virginia identifying Dr. Holladay’s medical practice.
Dr. Holladay cared for many patients, and numerous
long-time town residents remember that they, their siblings,
or their ancestors were born here. Now an 
accommodation in Virginia
, the  Holladay House continues
to offer care and hospitality to visitors.

Prominently located at the crossroads in the Town of Orange, The Doctor Holladay House (as it was then called) was a familiar landmark in town. In the 1920s and 1930s, the Holladays also constructed a small schoolhouse and a second home on the property. The house still stands on the west side of the Holladay House, but the schoolhouse is no longer extant. At first, the schoolhouse was just to the left of the main house, near the street, but the family eventually moved it to the rear of the house when the second home was built. Eventually, the Holladays sold the school house and moved it off of the property, presumably to a new but unknown location elsewhere in Orange County. Dr. Holladay’s daughter, Louise Holladay, taught local children in this one-room private schoolhouse, including the noted local historian, Civil War re-enactor, and Civil War Tourguide, Frank S. Walker, author of the authoritative book on Orange County history entitled Remembering: A History of Orange County, Virginia.

This photograph, taken in June 1937, shows Louise Holladay standing in the doorway of the one-room school house on the Holladay’s property in Orange, VA. This is the only known photograph of the school house. Note the Presbyterian Church across the street which still stands today. Neither the fence along the street nor the schoolhouse itself exist anymore, although one can still see the large stone slab on the ground that was once at the foot of the schoolhouse stairs, as well as remnants of the stone walkway that led to it. 

Louise Holladay, circa 1902. 

Lewis Holladay and his wife had six children while they lived at the Holladay House. Their oldest, Louise, never married and lived in what is now the Oak Room for many years. She remained in the house all her life, and cared for Dr. Holladay after the death of her mother. The Holladays' youngest child, Aubry Price Holladay, married William Hamilton and moved into the house next door, on the west side (which now stands on the site of the former schoolhouse). Henry Thompson was the oldest son. Lewis Holladay, Jr. and James Porter were twins, and Helen was their other younger sister. Both Aubry and Louise were school teachers, and a number of long-time town residents remember being their students. 


Sally Helen Price Holladay, wife
of Dr. Lewis Holladay, with
her twin sons, circa 1906.

As a prominent local physician, Dr. Holladay and his family received numerous mentions in the Washington Post’s social pages for attendance at various balls, horse shows, and other social engagements. Lewis Holladay apparently knew the duPont family well, for the social columns sometimes mention the two families together at the same functions.

The Holladays were also frequent attendees of the duPont's steeplechase races. The duPonts owned James Madison’s Montpelier for most of the late nineteenth and twentieth centuries, and operated a large-scale equestrian stable and race track there. The annual Montpelier Hunt Races have been a happy tradition in Orange, Virginia for over 75 years. The Hunt Race is still one of the most popular equestrian events in Virginia, boasting some of the oldest continually-used steeplechase hedge rows in the country. Attendees from all over the country stay at our Virginia bed and Breakfast to see this exciting event, where elaborate tents, tailgating, and traditional hats are the order of the day! For more information on the Montpelier Hunt Races, see our calendar of events and Virginia Travel Guide.


Journal of JP Dornan July 1918


Excerpt from the handwritten journal of J.P. Dornan,
published in the Fall 2007 Newsletter of the Orange
County Historical Society. On Thursday, July 25, 1918,
Mr. Dornan, an employee of the duPonts living at
Montpelier, wrote “Nine convalescent
soldiers arrived

on [Southern Railway train] #15. Mrs & Miss duPont,
       JPD Dr. Holloday, Dr Ricketts met them.”

During World War I, Dr. Holladay administered physical examinations for the Selective Service System. In 1918, the duPont family operated a hospital for convalescing soldiers, and Dr. Holladay attended these wounded heroes as they recovered in the serenity of James Madison’s Montpelier. In fact, the house used as the hospital at Montpelier now houses students and archaeologists during Montpelier’s annual Archaeology Field School.


When America entered World War II, Dr. Holladay was again called to serve the Selective Service System. One life-long resident of Orange, Virginia, Mr. Robert Lee remembers Dr. Holladay as the man who examined him and sent him to war.

In the tradition established by John Madison Chapman, two more wedding celebrations took place at the Holladay House. Helen Holladay and Aubry Holladay were married in the early 1930s. The Holladay House continues to be a popular wedding venue in Virginia. Visit our Weddings in Virginia page for more information!


After Dr. Holladay died in 1946, the house on the west side passed to his daughter Aubry and husband Henry Thompson. The house on the east side passed to his daughter Helen, and his son, James Porter. The main house passed to Louise and Lewis, Jr. Louise continued to live here, and at varying times she rented space in the Holladay House to boarders and to local businesses.

In 1984, Louise gave her interest in the property to her brother, Lewis Holladay, Jr. When he died, the property passed to his wife, Mildred. Mildred Holladay then passed the property to her son, Lewis “Pete” Holladay III.

The Holladay family remains important in the Town of Orange and in the quiet hamlet of Rapidan (a 10 minute scenic drive north of Orange). In Rapidan, many members of this historic Virginia family are buried in the churchyard of Waddell Memorial Church. Built in the 1870s, Waddell Memorial Church is one of the finest extant examples of nineteenth century “carpenter gothic” architecture in the Commonwealth of Virginia. Situated in a comfortable and quiet setting near the Rapidan River, a short visit to this scenic and architecturally important church is warranted!

Waddell Memorial Church in the serene hamlet of Rapidan, VA, just a short scenic drive outside of Orange. It is impossible to drive anywhere in our area without experiencing charming towns, historic churches, Victorian mansions, manicured horse farms, and Blue Ridge Mountain views. Our Virginia Bed and Breakfast is ideally situated at the epicenter of some of the most scenic roads in Virginia! 


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.