This hotel once specialized in extended, involuntary stays. The guests were some of the most dangerous and infamous characters around, and the bars kept things extremely exclusive. Sound terrible? Well, prison is no picnic.

The Liberty Hotel in Boston is housed in the former Charles Street Jail, and is one of the most historic and architecturally striking accommodations in the city. Today, you’re allowed to check in and out as you please, but the Liberty will definitely hold your imagination captive.

The Liberty Hotel is one prison where you’ll definitely want to do time. It was originally built as the Charles Street Jail in 1851.

Yelp/The Liberty Hotel

Thirty huge arched windows, each 33 feet high, were designed to let in natural light to some of the 220 granite cells.

Facebook/Liberty Hotel Boston

The prisoners’ cells were each 8 by 10 feet. Thankfully, current guests are afforded a bit more space to stretch out.

Yelp/Rob L.

The jail played host to a motley crew of famous inmates, including Sacco and Vanzetti, Malcolm Z, Michael Curley, World War II prisoners from German submarines, and even suffragists arrested for protesting in the streets.

The Liberty Hotel

The prison was converted to its present state in 2007. One of the best parts of visiting here is how much of the original character and history of the building has been preserved.

Yelp/Jackie S.

The room decor is playful and includes plenty of winks to the building’s former life.

Yelp/The Liberty Hotel Boston

Perhaps best of all, the hotel is completely dog-friendly.

The Liberty Hotel

Spend time in Alibi, one of the hotel’s gorgeous bars.

Yelp/Alibi Bar

Or maybe the fabulous Clink is more your style? The hotel’s restaurant serves much tastier fare than any inmate could hope to enjoy.

Facebook/The Liberty Hotel Boston

You don’t have to book a room at the Liberty Hotel to enjoy its restaurant, bars and atmosphere.

Facebook/Liberty Hotel Boston

Crime may not pay, but a stay at the Liberty will leave you rich in memories.

Yelp/The Liberty Hotel

You can find the Liberty Hotel at 215 Charles St., Boston. Find directions here, and check out their website here for rates and availability.

Yelp/The Liberty Hotel

Facebook/Liberty Hotel Boston

Yelp/Rob L.

The Liberty Hotel

Yelp/Jackie S.

Yelp/The Liberty Hotel Boston

Yelp/Alibi Bar

Facebook/The Liberty Hotel Boston

OnlyInYourState may earn compensation through affiliate links in this article.