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Beantown has history in spades but the old Charles Street Jail, which housed Boston’s notorious ne’er-do-wells between 1851 and 1990, is the only place you can spend the night surrounded by stories. Following a $150-million (U.S.) conversion, the jail became the Liberty Hotel in 2007, but recently had an $11-million guestroom revamp as part of the Starwood Luxury Collection.

Towering and brooding, the grey granite exterior is straight out of film noir and the Liberty Hotel has all of the gravitas you’d expect for a national historic landmark, but inside it softens with a warm welcome and a cold glass of bubbly at check-in.

The Charles Street Jail became the Liberty Hotel in 2007.

LOCATION, LOCATION

Boston’s Beacon Hill is within shopping bag swinging distance. Along the lantern-lined cobbled sidewalks of chi-chi Charles Street are antique shops and boutique bakeries galore. It’s a short stroll to Boston Common to join the historic Freedom Trail and the whole city is easily walkable – or runnable if you want to jog along Charles River with the Bostonians. North End’s winding streets of old Little Italy are nearby: Grab some cannoli from Mike’s Pastry and explore revolutionary Paul Revere’s house.

Suites are decked out in a palette of slates and cloudy greys, with studded plump headboards, safe-style cabinets and framed keys on the wall.

DESIGN

Previously the 298 rooms had been accused of being “vanilla,” but interior designer Bill Rooney’s do-over will change that verdict.

The reimagining takes a dignified rather than Disneyfied approach to incorporating the building’s hoosegow history: palette of slates and cloudy greys, tactile wallpaper decorated with subtle herringbone chain patterns, studded plump headboards, safe-style cabinets and framed keys on the wall. Hang your solitary sign on the door if you don’t want to be disturbed. Note, 18 rooms are in the historic old jail building, the remainder in an adjoining 16-storey tower.

Clink, a restaurant in the converted Charles Street Jail cells of Boston's Liberty Hotel.

EAT IN OR EAT OUT?

Solitary confinement (a.k.a. room service) is available, but it’s more fun to head down to Clink for chef Anthony Dawodu’s top-notch seafood dishes in the converted cells.

Celebrity mugshots line the walls of the cocktail bar, Alibi, which was once the drunk tank: some locals (hazily) remember spending a night there in the 1970s.

At the cozy Italian eatery Scampo (Italian for escape) in the old infirmary, try the inventive lobster pizza. Summertime means the Yard opens for al fresco yoga.

Scampo is located in the former infirmary.

BEST AMENITY

Watch out for whiplash when you enter the lively lobby. It’s impossible not to snap your head up in awe to check out the huge octagonal centrepiece of the original jail, complete with catwalks circling above. Architecturally it’s a wonder, but it’s also a buzzing bar space and home to Liberty Affairs – a series of regular fashion, art and yoga events for guests.

Boston's Liberty Hotel an $11-million guestroom revamp as part of the Starwood Luxury Collection.

ROOM WITH A VIEW

Planning a bank heist? Splash out on the 2,200-square-foot Ebersol Suite, complete with wrap-around balcony with views of the city and Charles River. If you’re doing less time then opt for a city-facing room in the tower on the 12th floor or higher for similar sweeping views.

IF I COULD CHANGE ONE THING

It’s surprising that a hotel with so much attention to detail missed the finishing touches, such as the light-coloured wood on the underside of the bathroom sink that gives away the painted dark wood.

The hotel's revamp did seem to miss a few finishing touches.

WHOM YOU'LL MEET

Sidle up to the bar and you might rub shoulders with visiting movie stars such as Matt Damon and Mark Wahlberg. Design-savvy travellers are attracted by the unique architecture and history buffs come to get a kick out of spending the night in the same place where legends in trouble with the law, such as Malcolm X, once bedded down.

The Liberty Hotel, 215 Charles St., Boston; libertyhotel.com; 298 rooms from $375 (U.S.)

The writer was a guest of the hotel.

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