In 1853, the Reverend Henry Ward Beecher purchased Blossom Hill, where the Cranwell Mansion now stands, for $4,500. He loved the views from the top of the hillside. His sister Harriet Beecher Stowe, who grew to considerable fame after writing Uncle Tom's Cabin, inherited the property after the Reverend passed away.  General John F. Rathbone purchased the property in 1869 and moved Beecher's farmhouse to the side of the hill so that the new home would have the commanding view of the countryside. The home he built, Wyndhurst, was enormous by any standards of the day.

At the same time, on the back side of the hill, another family was building yet another cottage. U.S. Naval Captain John S. Barnes, Flag Officer of the North Atlantic Fleet during the Civil War, purchased the land for $10,000 in 1882 and erected Coldbrooke, now known as Beecher's Cottage. John Sloane, a relative of the Vanderbilts and co-owner of the famous furniture firm, W & J Sloane, became the next owner of the property when he built his cottage in 1894. After tearing down Rathbone's Wyndhurst, Sloane constructed another Wyndhurst, which rivaled the enormity and elegance of the first. He also commissioned Frederick Law Olmsted, the landscape architect responsible for creating Central Park, to design the grounds.

This new Wynhurst stands on the hill today. After a brief stint as the Berkshire Hunt and Country Club in the 1920s, Edward Cranwell deeded the estate to the Society of Jesus of New England to be turned into a private school for boys named after the generous benefactor. After prospering for many years, the school slipped into decline, closing its doors in 1975. It was converted into a luxury resort and country club in 1993. In 2002 the 35,000-square-foot Spa at Cranwell opened with state-of-the-art facilities, offering over 50 services.