Jefferson designed all five of the Pavilions on the east Lawn, including Pavilion VIII, in fifteen days in June 1819. The appearance of the Pavilions was inspired by the classical orders as described in Andrea Palladio's Four books of Architecture and Freart de Chambray's Parallele de 1'Architecture. Pavilion VIII draws from the Corinthian order, adapted from Diocletian's Baths as illustrated by Chambray in the 1766 edition of Parallele.
Construction on this structure took place between April 1821 and September 1824 for a total cost of $10,786.86. Many of the contractors and workmen involved were already familiar to Jefferson. The lumber and carpentry were the responsibility of James Dinsmore and the bricks were supplied by John M. Perry and Abiah B. Thorn. Because the stone native to Charlottesville was too hard to carve into Corinthian capitals, Bernard Peyton sourced marble from Carrara, Italy. Artisans such as Edward Lawber of Philadelphia and W.J. Coffee worked on the glazing and ornamentation, respectively.
Many professors have lived and taught from Pavilion VIII. There are conflicting reports as to Pavilion VIII's first resident. Some sources give the distinction to Charles Bonnycastle, a lecturer on National Philosophy, others to Professor of Mathematics Thomas Hewitt Key. Each professor received a salary of $1,500 and an additional $25 for each student. By the mid-1800s, however, the Pavilions were no longer used for classes. University President Colgate Darden moved his office to Pavilion VIII in 1948.
After President Frank Hereford moved his offices to Madison Hall, restoration work began on Pavilion VIII. It had undergone several modifications since its construction, including expansions and painting. In 1985, restorations workers used surgical scalpels to remove layers of paint in order to determine the original colors. Individuals trained in graining, a process of finishing pine to resemble mahogany, were also employed. Ultimately, the restoration helped return Pavilion VIII to a close approximation of its original appearance.