The building dates back to the colonial era and the site was one of the original land grants from the English Crown to the New World.

[3] The property changed over time from a private home to a working farm, and then again to a riding academy.

In 1980 Harry Meyerhoff of St. Michaels, along with sons Tom and Jack, converted it into a six-room hotel with a small restaurant.

In September 1989, Sir Bernard Ashley purchased the property and began a two-year expansion that transformed The Inn at Perry Cabin into a 41-room luxury hotel.

By 2003, the company completed a $17 million improvement program designed by the architecture firm of Cooper, Robertson & Partners, which included three new buildings and 38 guest suites to bring the total room count from its original 41 up to 79.