The Windermere Hotel was designed by Richard Rickman of Peoria, Illinois and built in 1887 by bankers Charles and Clifford Anthony. Originally a summer cottage for the Anthony family, the building featured a tower typical of lakeside residences.

Patrick Doud purchased the cottage in 1904 and converted it to a resort hotel. Doud, an island contractor, also built the Governor's Summer Residence and Stonecliffe. When he added a third floor to the Windermere Hotel, the tower was removed and a sunroom added. The hotel is currently owned by Jeannette Doud (Mrs. Robert Doud) and her daughter, Margaret Doud.

Anthony Cottage in late 1800s	Windermere Hotel today
Mr. and Mrs. Patrick Doud	Robert Doud
Robert Doud and Wesley Maurer, Sr.