
Originally constructed for Charles O'Malley in 1852 as a beachfront resort, the Island House was one of the first summer hotels on Mackinac Island. In 1865 Captain Henry Van Allen, a Great Lakes skipper, purchased the resort, thus beginning a family tradition that would last nearly 75 years. During this time he moved the hotel about 300 feet off the shore to its present location to allow for future expansion. Under Captain Van Allen's direction,the Island House was deemed the Island's "best family hotel" as Mackinac Island was voted the most popular summer destination in America.

~~
Upon his passing, Captain Van Allen bestowed the property to his daughter. Mrs. Rose Van Allen Webster became proprietor of the hotel in 1892. Together with her husband, whom she met while he was stationed at Fort Mackinac, the Webster's added the distinctive looking East and West wings in 1895 and 1912. The Island House enjoyed the benefits of these additions for the next 25 years as Chicago, Detroit, St. Louis and New York socialites were treated to afternoon high teas and full orchestra ballroom dancing. Mrs. Webster retained ownership of the Island House until her passing in 1938.
