Percy Dwight Bentley was born in La Crosse, Wisconsin on January 30, 1885, the son of a banker. He studied architecture and graduated from Ohio Wesleyan University in 1907. He did further study at the Armour Institute of Technology (now Illinois Institute of Technology) in Chicago. While in Chicago Bentley spent a great deal of time at the Art Institute of Chicago. Both Louis Sullivan and Frank Lloyd Wright maintained offices in close proximity to the Art Institute and Bentley was accustomed to seeing them on a regular basis. This heightened awareness of them led to his study of their styles and philosophies.

Bentley returned to La Crosse before completing his studies and became an apprentice in the office of Wells E. Bennett. He left shortly thereafter with a residential commission from Edward C. Bartl and opened his own office in 1910. He hired Otto A. Merman as his draftsman, and eventual partner, and they continued to design primarily Prairie style residences in Wisconsin and Minnesota. Bentley occasionally partnered with other Prairie architects on his commissions. He had George Mann Niedecken design the furniture, lighting and carpeting for the Henry A. Salzer house of La Crosse, Wisconsin in 1912.

The partnership of Bentley and Merman ended with the death of Merman in 1935, and Bentley left La Crosse for Oregon in 1936.