The original building of what is now The Kennebunk Inn was built as a private residence by Phineas Cole in 1799. Mr. Cole later sold the house to Benjamin Smith, whose family resided there until 1875. In 1876 Dr. Orrin Ross bought the home, giving it to his son, Dr. Frank Ross, in 1880 as a wedding present. Dr. Frank Ross specialized in obstetrics; reportedly never losing a mother in over 1,000 deliveries.

Dr. Frank Ross died in 1926 and the property was sold to Mr. and Mrs. George Baitler. In 1928, George Baitler converted the private home to a hotel known as "The Tavern," adding a 2.5 story wing to produce a total of 50 guest rooms. In the late 1930s the name of the hotel was changed to The Kennebunk Inn.

Another distinctive feature of The Inn is its "haunted heritage." Rumor has it that Silas Perkins, one of The Inn's clerks who passed away in the mid-twentieth century, continues to inhabit his former place of employment – his presence visible occasionally by flying or falling wine glasses and other objects.

In its more than two hundred year history, The Kennebunk Inn has survived and supported both private and public purposes during the tenures of over forty U.S. presidents (one of whom, President George H. W. Bush, resides just a few miles away during the summer months). The Inn is proud to have a part in both the history and the future of what singer James Taylor aptly calls "the great state of Maine".