Charles Ashley Hardy, a prominent Boston stockbroker, acquired the land that now houses Chatham Bars Inn in 1912. A year later the Main Inn, nine seaside cottages, and a golf course had been constructed. And at four o'clock in the afternoon on June 9, 1914, Hardy officially opened Chatham Bars Inn, an elegant oceanfront resort surrounded by piazzas and terraces. 

Overlooking Pleasant Bay and the Atlantic, with "surf and still-water bathing, sailing, and motor boating in land-locked waters, the best of deep-sea fishing, harbor fishing, and shore bird shooting," it became a popular hunting lodge for well-to-do sportsmen. In 1915 a pier was constructed to connect the main beach to a sand bar and in 1922 the golf course opened to the public. 

A tragic hunting accident brought Hardy's life to an abrupt end in 1924, and the ownership of the hotel was transferred to newly created Chatham Associates. During World War II, the Chatham Bars Inn served as a welcome retreat for the Dutch Royal Family while they were in exile in the United States (other famous guests include Henry Ford, Henry Morganthau and William Rockefeller). In 1953 Chatham Associates sold the inn to a local businessman, and in 1961 the hotel pier was dismantled. 

In 1988, Chatham graduated into a year-round resort and five years later a series of extensive renovations began, including a complete restoration of the Main Inn that elevated Chatham Bars Inn to its regal, relaxing present-day status.