The 1885 Lake's Atlas of Shenandoah and Page Counties notes the "Shenandoah House" stood on this site. It would have served travelers on the Valley Turnpike and from the nearby rail line.
Sometime in the last decade of the 19th century/first decade of the 20th century the Holtzman family purchased the structure and renamed it the Hotel Holtzman. It was one of many such businesses they operated in several county towns.
In 1907 the Shenandoah Herald reported it was one of the last two bars operating in the Town of Woodstock. The Holtzman Hotel's bar would operate until alcohol was outlawed in 1907. At the time the Shenandoah Herald reported only it and the Holtzman Hotel across the street were operating bars. It, and the Geary Hotel across the street generated over $500 annually in town liquor taxes so their business must have been brisk. Lawyers representing the two businesses fought efforts to outlaw alcohol, but they were unsuccessful. The "dry" won by one vote.
On September 26, 1916 the Holtzman Hotel was the site of an address by Lila Valentine, President of the Equal Suffrage League of Virginia. The Shenandoah Herald noted it was an "excellent address" and would have been designed to promote the women's suffrage movement in Shenandoah County.
The hotel would operate into the 1920s when it was purchased by the Dalke Family. They opened the Uptown Theater here and rented commercial space in the front to a barbershop. After the Dalke's opened the Community Theater two blocks away the Uptown Theater primarily showed westerns and other cheaper films.
In 1947 a fire heavily damaged the building and it was demolished. In 1974 Shenandoah County purchased this land and built a new circuit court house here.