Liberty Hotel, Boston
This storied 19th-century Charles Street Jail in tony Beacon Hill lay vacant for 15 years before developer Carpenter & Company turned it into one of Boston’s most stylish hotels in 2007. The original four-wing main structure has 18 rooms, a tapas restaurant called Clink and a cocktail bar named Alibi. Across a courtyard that used to be the prison exercise yard is a museum dedicated to the building’s history (forger Frank Abagnale, Jr. was a former inmate), and a modern 16-story tower with 280 rooms topped by a sprawling President’s Suite. Sit on its terrace deck with views of the Charles River, Cambridge and Boston below, and you may very well turn away the rescue helicopter.