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.

Anthony Cottage in late 1800s

Windermere Hotel today