Former Jailhouse Is Now One of the Hottest Hotels in Boston

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Deal Expert, New York
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An overnight stint in the slammer isn’t something to brag about. At least not until the former Charles Street Jail became the swanky Liberty Hotel in Boston’s Beacon Hill and offered a Travelzoo deal saving 45% on winter stays.

The building’s infamous roster of guests has included Boston’s most wanted, but two multi-million-dollar renovations and 165 years later, it has evolved into one of the city’s poshest hotels. Its criminal past is not lost on the Starwood Luxury Collection property — the hotel embraces it with a unique sense of humor.


Don’t expect to find “Do Not Disturb” signs hanging on doorknobs. “Solitary” key rings mark your room confinement.

The Liberty features several restaurants and bars aptly named Clink, Catwalk, Alibi and the Yard.

Award-winning chef and Boston local Lydia Shire is the culinary genius behind Scampo (Italian for “escape”), which Esquire Magazine named among the Best New Restaurants during its inaugural year.

Not-so-subtle reminders of the restaurant’s yesteryear, the preserved original brick walls and iron cell doors are focal points in the décor.

A photo posted by Michael Traynor (@mjtraynor) on

Ironically, the jail’s former drunk tank, where the intoxicated were kept overnight, is now Bar Alibi – one of Boston’s hottest see-and-be-seen bars.

But if you’re interested in solitary drinking, your room comes with a fully stocked martini bar – a perk that was not awarded to the prisoners.

A photo posted by @yuliao77 on

The 8-by-10-foot ft. jail cells have since been quintupled in sqaure footage and the newly-renovated rooms feature floor-to-ceiling windows overlooking Cambridge and the Charles River.

The jailhouse chic aesthetic extends itself to the interior design of each guestroom with tally-mark pillows, framed keys, scales of justice and safe nightstands.

A photo posted by Mrs.P | ??? (@ver0ject) on

Even dogs get special treatment at the Liberty, including dog beds and treats.

There’s even a dedicated “Yappie Hour” from May to October.

And during the winter season, the Liberty hosts a variety of events from Saturday workouts with Equinox instructors to interactive fashion shows every Thursday.


For $149-$159 per night, Travelzoo members can check into a Superior Room at the historic Liberty select dates through March.

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