A stretch behind bars is probably not something that makes many travellers’ to-do list, but this line-up of prison hotels just might. From plush 5-star resorts to cosy hostels, these repurposed penitentiaries come with a history, and plenty of character. On Booking.com, you can sentence yourself to an extended stay without committing a single crime…

HI- Ottawa Jail Hostel – Ottawa, Canada

Staying true to its 150-year history as the Carleton County Gaol, this hostel gives you the choice between bunking up alongside fellow ‘inmates’ or sleeping in your own three by nine feet cell. Thankfully, the original prison doors unlock from the inside these days, and you’ll even be allowed out the next morning.

Rise at 11:00 am for your (optional) induction – a free 30-minute tour around the premises, covering the building’s history and a few eerie ghost stories as well.

Långholmen Hotell – Stockholm, Sweden

At Långholmen the cells may have had a cosy upgrade but the hotel’s prison history is far from forgotten. The island’s museum is free to guests and explores conditions from the 18th century up until the jail’s closure in 1975.

Think you’d be cunning enough to escape? Tackle the hotel’s strategy game and try it for yourself. Whatever the outcome, there’ll be a 3-course meal waiting at the end – and canteen slop it is not.

Best Western Premier Katajanokka – Helsinki, Finland

Hotel Katajanokka closed the door behind its last inmate in 2002, and the red brick premises have since undergone extensive renovations. Aside from a few key features such as the gated central corridor and perimeter walls, the property is everything you’d expect from a contemporary hotel.

Metre-thick walls now keep the noise out, instead of keeping you in – and a pair of prison-striped slippers are all that’s left to remind you that your spacious suite was once supposed to be a punishment.

Four Seasons Istanbul at Sultanahmet – Istanbul, Turkey

Looking more like a palace than a prison, you’d never guess that this luxurious five-star hotel was ever anything but. Cells have given way to grand suites decorated in traditional Turkish

Some clues do remain, however. Peer a little closer at the marble pillars and you just might spot a message or two carved into the stone by prisoners whiling the hours away.

Malmaison – Oxford, England

Malmaison contrasts plush modern furnishings with a prison aesthetic, for a unique boutique-behind-bars kind of vibe. You can reserve a room in the A-Wing for a stay in the fanciest cell you’ve ever seen, or assert yourself as top dog in an Executive Suite.

This isn’t just your ordinary jailhouse, either. It’s actually Oxford Castle (an 11th-century Norman stronghold) so its unusual story extends far beyond its 100-year stint in the criminal justice system.

The Liberty – Boston, USA

The Liberty is proof that an upmarket hotel can fully embrace an unsavoury past – employing a slew of architects, historians, designers and conservationists to perfectly preserve the original features of Charles Street Jail.

Laced with key motifs and tally-chart prints, even the extravagant suites hint at the hotel’s former life. As for food and drink? You can set your story straight in the Alibi bar, dine out in CLINK. or head to The YARD for a taste of freedom.

Hostel Celica – Ljubljana, Slovenia

Hostel Celica’s prison home was saved from demolition by a creative collective, who took up residence within its walls. Over time, each cell was transformed into functional art and opened up as an affordable, eco-conscious space for travellers to stay.

You’ll be randomly assigned your digs upon arrival – with no two rooms alike, aside from the barred door that clanks shut behind you. And if you’re intrigued by Celica’s shadowy history, you can head down to the Museum of Confinement, hidden away in the bowels of the basement.