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Discover the past lives of these historic hotels

    Want to spend the night in a former jail or a Gilded Age mansion? Guests can take a trip into the past at these historic properties.


    The Liberty Hotel in Boston was once the Charles Street Jail.

  • Charles Street Jail

    • Hotel: Liberty Hotel
    • Pearls: 4
    • Location: North End and Beacon Hill, Boston
    • Price: $333/avg. per night


      For nearly 150 years, the tall granite building at 215 Charles Street was known as the Charles Street Jail and housed some of Boston's most heinous criminals. In 2007, after a painstaking restoration that preserved elements of the prison design, it reopened as the Liberty Hotel. The result is stunning, with 298 rooms, a 90-foot-tall atrium, winding catwalks, and high, circular windows that flood the lobby with light.
    The New York Palace was formerly a private mansion during the Gilded Age.

    The New York Palace was formerly a private mansion during the Gilded Age.

    Gilded Age Mansion

    The Hotel Monaco began as a post office in the 19th century.

    The Hotel Monaco began as a post office in the 19th century.

    19th-Century Post Office

    • Hotel: Hotel Monaco, Washington D.C.
    • Pearls: 4
    • Location: Penn Quarter, Washington, D.C.
    • Price: $326/avg. per night


      There are seven Kimpton-brand hotels in the District, but the Monaco is the only one in a National Historic Landmark building. The Greek Revival General Post Office, designed by Washington Monument architect Robert Mills and finished in 1839, was reborn as this 183-room hotel in 2002. The four-floor lodging takes up an entire city block on the eastern edge of the Penn Quarter neighborhood.