The coolest hotel in Boston is by far the Liberty Hotel. What was once used as a prison, the semi-newly constructed building has transformed into a posh boutique hotel. For 120 years it held some of Boston’s most notorious criminals, not until 1990 were the last prisoners transferred, and 11 years later construction for the hotel was on its way. Although the hotel definitely plays up the jail-house theme, the eery feeling tends to go away once you step into the extremely lavish lobby and view the cost of staying the night. It’s currently out of my price range, but its a very trendy, fun place to go have a drink.