
“You’re in Cell Eight,” I’m told as I’m led up a narrow, winding staircase to the second floor. The key turns in the lock, the heavy wooden door creaks open, and I step into a smallish but perfectly formed room, with wrought iron bed and bedside locker, and sparkling bijou en suite. No padded walls or window bars.
This new 10-room place to stay on the eastern edge of Winchester calls itself the Black Hole B&B, but it’s not really a B&B in the traditional sense. It’s not part of someone’s house (no need to sneak in quietly if you get back late), but then there’s no bar or receptionist on call after hours either.
What it is, I quickly discover, is a very comfortable, relaxed and tad quirky place to stay. The prison theme, built around the rather beautiful room doors (solid wood on one side, heavy iron on the other, dating from around 1890, possibly from Clerkenwell gaol, pictured below), feels fun rather than gimmicky. The hallways are lined with prints of authentic black and white mug shots – the likes of John Hollins, banged up in 1889 for larceny and warehouse breaking, who “works alone”. And in the red-walled breakfast room, your full English is served on prison-style tin plates.
Spread over four storeys, all the rooms are different (pictured right) – mine has great views west over the cathedral. Cell Seven feels like a library, with its bookshelf wallpaper, Ten is big with a standalone bath and kids’ twin room through what looks like a cupboard, while the “Padded Cell” on the ground floor has realistic concrete-effect wallpaper. There’s a small but lovely rooftop terrace, too.
Opened last September, the Black Hole is the latest venture from eccentric local entrepreneur David Nicholson, who also owns the Black Boy pub next door, the Michelin-star Black Rat restaurant opposite and the Black Bottle wine bar up the road.

We start off with a peek inside the pub, which dates from the 1700s. The warren of rooms is chock-a-block with curios and a strange assortment of stuffed animals – a giraffe’s head here, a donkey there. There are stacks of board games, an open fire roars, dogs are welcome. It’s still very much a locals’ pub with a variety of ales on rotation and selected craft beers. It does decent pub grub at lunch and dinner (and bangers in baguettes in between), but we’re off to the Black Rat (pictured right) for more refined fare.
All beamed ceilings, exposed brickwork and yet more curious artefacts, it was a raucous gay pub in a previous life. “I remember a man in a long black dress with a ZZ Top beard standing just over there,” says my friend, who lives in the town.
Tonight it’s full of a more conventionally dressed crowd enjoying cocktails in the bar upstairs and tucking into chef Ollie Moore’s “Modern British” menu. It’s creative and lick-your-plate-clean delicious. Scoring particularly highly was the dish of charred fillets of lemon sole, crab and sweetcorn rice with Alexander buds.
To check out the full quartet of Nicholson’s mini-empire, we venture up the road to the Black Bottle, his far from poncey wine bar, which again is big on character and low on pretension. Wines are self-service from vending machines (from £3.60 a glass) – put money on a charge card and away you go. There are two white rooms, two red, knowledgeable staff are on hand to help you decide, plus there are iPads with information on vintages and wine regions if you want to find out more. And if you’re peckish, cheese and meat platters cost a tenner.

The next day, after a comfortable night in my cell, we wander around the pretty cathedral square, stroll along the water meadows and climb St Catherine’s hill.
Winchester is one of those towns that divides opinion – it’s been named the best city in which to live in the UK but also bagged fourth place in a book called Crap Towns. Whatever you think, there are a few worthwhile sights, OK-ish shopping, decent places to eat and some good walks on the doorstep.
But for a night or a weekend away, the Black group has plenty to keep you busy. The B&B is somewhere you could hole up for a romantic weekend, or take over with a group of friends for a special occasion, eating in the pub or restaurant, as budget allowed, maybe fitting in a spot of wine-tasting, too. It adds a much needed sense of fun to the accommodation choice in Winchester. I’d certainly be happy to be locked up there for a while.
• Accommodation was provided by The Black Hole B&B, Wharf Hill (01962 807010, theblackholebb.co.uk); all rooms £100 a night B&B
Ask a local
Sophy Williams, founder of the Winchester Oracle online events guide
• Shop
Situated in warehouses on the outskirts of town, Molly’s Den is an emporium of endless rooms of antiques and vintage knick-knacks sold by individual sellers.

• Walk
Stroll down the river Itchen from Winchester city centre to Twyford, and have a cup of tea in the lovely Bean Below cafe. The river meanders past beautiful houses and scenic gardens; the walk takes about 40 minutes on a slow day.
• Art and theatre
Chesil Theatre, housed in a 12th-century listed church, often puts on performances from the Winchester Dramatic Society, which was formed over 150 years ago. And at Winchester Discovery Centre, there are always exhibitions, shows, comedy, live music and theatre.