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The Liberty Hotel, Boston
Rates: From $295

Highlights: It's no mystery how this hotel got its name: The building began life in 1851 as the Charles Street Jail. A thorough renovation (the last of the prisoners left in 1990) has mixed a few historical details, such as vestiges of jail cells in the lobby, with luxurious amenities befitting the Liberty's location in Beacon Hill. Travelers can take advantage of the 24-hour fitness center, free overnight shoeshine, VoIP phones with touchscreen hotel services, and a special "solitary dining" room-service menu, where you can mix and match items to customize a meal.

Don't miss: The cheekily named Clink restaurant.

NEXT: Trump International, Chicago
Last updated May 23 2008: 12:36 PM ET