Located on the grounds of the Cranwell Resort, Spa & Golf Club, this property was originally owned by Reverend Henry Ward Beecher, who sold it to John Sloane in 1894. Sloane built a Tudor-style cottage, which he named Wyndhurst, and commissioned Frederick Law Olmsted, Sr. to design the grounds. In 1926, the property was bought by a developer from Florida and converted into the Berkshires Hunt and Country Club; Wayne Stiles and John Van Kleek were commissioned to design the club’s 18-hole golf course.
In the late 1930s, Edward Cranwell deeded the property to the Society of Jesus of New England, which founded the Cranwell Preparatory School, operated on the site from 1939 to 1975. By the time the school opened its doors, most of Stiles’s original holes had become overgrown. Several students and teachers uncovered them and the school operated a nine-hole course for many years.
With the exception of the first three holes on the front nine, the course reflects Stiles's typical approach. Holes 7 and 8 align parallel to the original entrance drive, with the 7th hole leading uphill to a shelved green by the porte cochere of the estate. Holes 9 through 14 each lies within its own landscape setting. Stiles’s design also included fairways edged with trees and carefully orchestrated vistas to the surrounding mountains.
The mansion and golf course were converted to a resort in 1993. In the early 1990s many of the tees and bunkers were reconstructed with Stiles’s original design in mind.