The Liberty Hotel Review: A Former Prison Turned Lively Hotel in Boston’s Beacon Hill Neighborhood

The entrance to The Liberty Hotel in Boston. Photo by Jamie Sanders

There are fewer hotel experiences more unique than staying in one that used to be a prison. There is a current trend toward reimagining old buildings like schoolhouses, convents, and, yes, prisons, into hotels —but The Liberty Hotel in Boston, which opened back in 2007, took on the challenge earlier than most.

I’m no stranger to Boston; my family vacationed there in the late ’90s and I’ve been visiting my brother there multiple times a year since he first went to Boston University in 1999. But on my most recent visit, I was treated to a stay at The Liberty Hotel, and I must say, I couldn’t wait to check in.

The Best Spas in Boston

The Liberty Hotel was designed by Bill Rooney, whose work has also included The Peninsula New York and The Peninsula Chicago. The hotel, which is a Luxury Collection Hotel, has 298 rooms and suites with playful nods to the building’s past as the Charles Street Jail.

A set of escalators leads up to the hotel lobby. Photo by Jamie Sanders

As soon as you pull into the circular drive, the immense stone structure looms up at you. Although the prison closed in 1990, the building is a National Historic Landmark, which means much of the building’s original design bones are still there to this day.

Heading up the escalator to the lobby, you can’t help but feel a sense of awe as you take in the exposed-brick atrium, 90-foot-tall rotunda, and 33-foot-high arched windows. The effect is dramatic and breathtaking.

The hotel’s exposed-brick atrium features dramatic arched windows and a tall rotunda. Photo by Jamie Sanders

There’s no denying the overall attitude and aesthetic of The Liberty Hotel — it’s incredibly lively. The lobby features a bar, overstuffed leather armchairs and couches, and loud music pumping through the surrounding speakers.

I was shocked and delighted, however, to discover that the actual hotel rooms are blissfully silent. As soon as you step off the guest elevators, you’re treated to an almost reverent hush.

The hotel’s “Do not disturb” sign is a strip of cloth that says “SOLITARY” attached to an oversized metal ring. Photo by Jamie Sanders

The rooms themselves are an oasis amongst what may be considered chaos below. My room had a delightfully comfortable king bed with an almost-imposingly large navy leather headboard taking up one wall.

Each of the hotel’s 298 rooms and suites have been renovated to maintain the historic nature of the landmark building. Photo by Jamie Sanders

In one corner is a rich, sleek leather armchair with a matching ottoman. The floor-to-ceiling windows overlooked the entire city of Boston — I could see the famed CITGO sign blinking on and off, and landmarks like the Prudential Center and Fenway Park.

My room also included a comfortable leather armchair and floor-to-ceiling windows that showcased city views. Photo by Jamie Sanders

The bathroom was large and included many creature comforts; my favorite among them was the plush terrycloth robe and the Molton Brown products in the shower.

There is a separate glassed-in shower with a rain showerhead, and a large soaking tub perfect for taking a bath at the end of a long day.

The spacious bathroom included a deep soaking tub. Photo by Jamie Sanders

Throughout the space, you’ll find nods to the hotel’s former time as a prison. Framed jail keys and maps of the city line the walls, and the rug features a pattern of jail keys and clocks.

My favorite was the “Do not disturb” sign, which is a strip of cloth that says “SOLITARY” attached to an oversized metal ring.

Room decor included framed jail keys, maps of the city, and more. Photo by Jamie Sanders

There’s a vast array of restaurants and bars to choose from here, which are all — of course — prison-themed. My family dined at Scampo (which translates to “escape”), an upscale Italian restaurant with unique takes on pizzas and pastas.

We dined at Scampo, an upscale Italian restaurant with special takes on pizza and pasta. Photo by Jamie Sanders

Standouts included Oglio e Olio and Pomodoro Pastas and the Classic Tomato, Fior di Latte & Basil Pizza. We also tried a lobster pizza and tempura green beans, which were equally delicious.

You can also dine at Clink, or have drinks at Liberty Bar or Alibi, the latter of which was the old drunk tank on the first floor.

Scampo is a culinary destination created by legendary Boston-based Chef Lydia Shire translates into Italian-inspired cuisine, drawing on flavors from the Mediterranean and Middle East. Photo by Jamie Sanders

Hotel guests and patrons alike can also take part in Liberty Affairs, the hotel’s various events. In fact, there was a Fashionably Late fashion show happening the night I checked in, which featured a variety of men’s and women’s activewear. There are also yoga classes through Equinox, evening concerts, and nightly DJ sets.

The Liberty Hotel had been on my list for years, and it did not disappoint. The only sad part was having to check out at the end of my trip. If you are visiting Boston, this is absolutely worth adding to your list.

Built in 1851 and formerly the Charles Street Jail, the hotel is now a national historic landmark.. Photo by Jamie Sanders

For more information and to book a stay at The Libery Hotel, visit their website or call (617) 224-4000. For special packages, click here. Follow on Instagram: @liberty_hotel

215 Charles Street, Boston, MA 02114

More luxury destinations:

Sun, Sand and Ocean Waves Set the State for Renewal at Monterey Bay’s Sanctuary Beach Resort

The Newly Rebranded Archer Hotel Brings Old World Hospitality to Alexandria, Virginia

[Photos by Jamie Sanders]

Jamie Allison Sanders is an LA-based writer with 20+ years of experience in fashion, beauty, and lifestyle. After 12 years in New York City and a brief stint in Pittsburgh, she (finally) relocated to Los Angeles in 2015.

Her work has appeared in InStyle, People, BuzzFeed, Insider, Today, Harper’s Bazaar, and Well+Good, among others. She also started her own blog, The Beauty of Life, in January 2007.

Over the years, she’s cultivated her obsessions of bold nail polish, candles, Bonne Bell Lip Smackers, and strappy heeled sandals. When Jamie isn’t working, you can most likely find her exploring the Los Angeles bar and restaurant scene, traveling, or enjoying time at a spa.