Fall Getaways Near Westchester County 2011: The Liberty Hotel in Boston, MA

Give Me Liberty

The Liberty Hotel

215 Charles St // Boston, MA
(617) 224-4000 // libertyhotel.com

Distance from White Plains: 4 hours

A trendy Beacon Hill crowd starts to arrive at the Liberty Hotel lobby. You grab a drink from the lobby bar—perhaps a Juniper Blossom, made of Tanqueray, St. Germain, and grapefruit—and look out onto the soaring four-story atrium. The grand space is marked with towering arched windows, wrought-iron chandeliers, and mahogany furniture. If you didn’t know, you might never guess that the place was once a jail.

- Advertisement -

Yes, until the 1990s, the hotel was the old Charles Street Jail, which housed inmates such as Sacco and Vanzetti and James Michael Curley (who was imprisoned there for fraud but ran a successful campaign for alderman while he was interred). Developer Carpenter and Company and architect Cambridge Seven Associates teamed up to repurpose the property. The old cellblocks are now stylish catwalks with sitting areas for guests, the original “drunk tank” has (fittingly) been turned into a bar, and some of the original jail cells are now dining nooks at the on-site restaurants. Eighteen of the 298 guest rooms also are set up within the landmark jail building (with the rest in a newly constructed 16-story tower).

While there are many nods to the Liberty Hotel’s history, thankfully, there’s nothing prison-like about the guest accommodations. Spa-like is more apt, with luxurious bathrooms with separate deep bathtubs and rainfall showerheads. And, with a spot right at the foot of the Longfellow Bridge, many of these rooms look out over the Charles River.

That location also makes the hotel the perfect jumping-off point for exploring the rest of the historic Beacon Hill neighborhood. Walk the cobblestone avenues, browse the tony shops on Charles Street, and gawk at houses that once belonged to the likes of Louisa May Alcott and Sylvia Plath. Hike or bike down the riverside Esplanade, or take a walk to the gold-domed Massachusetts State House and Boston Common.

But, when those historic gas lamps start to shine, it’s time to return to the Liberty. There are a few different bars and restaurants in the hotel—Scampo for Italian cuisine infused with global influences, Alibi for loud music and cocktails, and the perfectly named Clink for drinks and modern American cuisine or classic New England seafood, among others—but they all seem to spill out into the hotel lobby, which becomes a scene at night. Which may be the first time it’s said that people want to end up in an old jail after a night of partying.

The Nitty-gritty: Rates for standard rooms begin at $259 and suites begin at $550 per night, based upon seasonality and double occupancy.

Our Westchester Home Design Awards event is June 26!

Our Wine & Food Festival returns June 4-9!

Our Wunderkinds event takes place on May 23!

Our Best of Business Ballot is open through May 15!

Our Healthcare Heroes Awards event takes place on May 9!

Our Westchester Home Builders Awards take place on April 4!

Our Diversity, Equity & Inclusion Forum is March 14!

Unveiled: A Boutique Bridal Brunch is February 25!

Our Best of Westchester Elimination Ballot is open through March 6!

Holiday flash sale ... subscribe and save 50%

Limited time offer. New subscribers only.