Last Updated on February 22, 2024
Where to stay and eat in Winchester, Hampshire
The historic city of Winchester in Hampshire is just an hour from London by train; a great place to visit it’s right in the heart of the English Countryside. While it has the usual chain restaurants found in most city centres these days, there are also plenty of unique independent bars and restaurants and on my recent visit, I managed somehow to sample quite a few of them. I also had the chance to try two delightful places to stay in Winchester, both full of character and charm; the Old Vine, in the heart of the city and The Black Hole, a short distance on foot from the centre on Chesil Street.

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Where to stay in Winchester – The Old Vine Inn
This grade II listed Inn is conveniently situated very close to Winchester Cathedral and the High Street. It’s extremely popular during the day and the evening and has an appropriate slogan of Eat, Drink, Sleep.
The bedrooms upstairs at The Old Vine Inn are spacious with plenty of storage. There are tea and coffee making facilities, including a Nespresso machine, the little fridge contains complimentary water, bottles of Luscombe orange juice and a small bottle of fresh milk. The bathroom had a bath with an overhead shower, flannels and plenty of towels, dressing gowns and toiletries.

The Old Vine is a very old building so the floors did slope in places and it was a bit creaky when other guests were moving around. The bed was very comfortable and the hotel was remarkably quiet for its location, though I did stay on a Monday night and I wondered if it might be much noisier at the weekend.

For breakfast the following morning there was a good choice of cereals, fresh fruit and hot options. I chose fruit and yoghurt followed by scrambled eggs, local Hampshire bacon and mushrooms. There was a plentiful supply of toast to accompany the cooked breakfast and a cup of freshly made coffee.
For convenience on a short break to Winchester, The Old Vine Inn has to be a good choice for somewhere to stay, close to all of the major attractions in the city.
Dining in Winchester – Lunch at the Royal Oak

The Royal Oak is said to be the oldest bar in England, found down a narrow passage off the High Street. It’s a cosy space with friendly service offering beautifully cooked, hearty, pub food. I was visiting for lunch on a chilly day so I chose a ham and cheese toastie with a side of chips. It was just what I needed to keep me going on a busy day of sight-seeing in the city.

Dining in Winchester – Dinner at Rick Stein
Having grown up in Cornwall, I am a fan of Rick Stein, having eaten at the Seafood Restaurant and the bistro in Padstow but did not realise that there was an outpost in Winchester.

I love seafood and Rick Stein is one of the best restaurants to dine at if you are looking to eat high-quality fish and shellfish. I chose the Andalucian fritters with brown shrimp and spring onions to start. The fritters were crisp and delicious and perfectly accompanied by a glass of Rick Stein’s Spanish white wine, Viura/Verdejo Castilla y Leon. I’m a huge fan of crab so to follow I chose the linguine with white crab meat, olive oil parsley and chilli. The pasta was very tasty with the chilli adding a touch of warmth to the dish.
A light and airy space this restaurant is filled with large seascapes on the walls from the painter Kurt Jackson, originally from Dorset, who now lives and works near St Just in Cornwall.
Dining in Winchester – Lunch at The Chesil Rectory
This quaint and charming building is just over the bridge from the City Mill, another of Winchester’s old historic buildings of which there are many – it is undoubtedly one of the best preserved medieval buildings to be found in Winchester, dating from around 1425.

I wished that I had more of an appetite to do it proper justice and would certainly return. I visited for lunch and it was busy so booking in advance would be recommended.
The low ceilings of this old building make it especially cosy. The extensive menu features local produce where possible, such as lamb from Cobley Wood Farm, mushrooms from Stockbridge and black pudding from Laverstoke Farm.

You can choose from the lunch set menu or the A La Carte menu. I decided on the A La Carte and dined on rosemary skewered king prawns with butter beans and aioli, followed by a delicious chocolate and orange Jaffa delice with candied zest and bitter orange sorbet. To accompany my lunch a glass of the local fizz – from the Hattingley Valley Vineyard.
Dining in Winchester – Dinner at The Black Rat
This Michelin starred Restaurant is just over the road from the Black Hole. Set in an old building which was previously a pub, the interior is cosy, with warm, subtle, lighting. The pictures on the walls feature sketches of the anatomy of the human body, another unusual theme. The staff are very attentive and welcoming, readily giving me suggestions when I asked for their recommendations.

As an aperitif, I chose the spiced Negroni cocktail made of pink peppercorn gin, Martini Rosso and Campari. It was an excellent start to my meal on what was a cold evening. The menu has a good choice of meat, fish and vegetarian options. I could have happily chosen several dishes from the menu as they all sounded very tasty. As well as the comprehensive wine list there is a cocktail list and even a separate gin menu.

For my starter I chose the sea trout with Cornish crab, bisque ice cream, cornbread and avocado, it was light and extremely tasty. To drink a glass of Semillon Sauvignon.

For my main course, I opted for the Yorkshire grouse with carrot, black garlic gnocchi, rowanberry and crab apple. It came beautifully presented and was full of flavour. To accompany the main course, a glass of Pinot noir from White River in New Zealand.

For dessert I plumped for the madeleines with butterscotch sauce, these were soft and delicious having been freshly baked, there is a short wait for this dessert. In the centre of the dish was a small pot of hot, sweet, butterscotch sauce.

Having dined on an amazing meal I made my way back to The Black Hole for a good nights’ sleep. The Black Rat is very popular so it may be difficult to get a table at short notice. Making a reservation in advance is essential.
Where to Stay in Winchester – The Black Hole
This quirky ten-room bed & breakfast is part of the Black Group; The Black Hole, The Black Boy Pub, The Black Rat Restaurant and the Black Bottle.

A short distance by foot from the centre of Winchester The Black Hole has no off-street parking, but you can park in the Chesil Street, 24-hour car park having dropped off your bags. The Black Hole is themed on a prison with the bedrooms being called cells, I was staying in Cell 3. The doors to the cells are heavily studded wood on the outside with metal on the inside. The rooms are sparsely furnished with the minimum furniture including a metal, safe like box as a bedside table.

The bedstead was metal, and the bed was covered by a bedspread with signage for The Black Rat restaurant. The small ensuite bathroom contained a walk-in shower with toiletries, a sink and toilet. The fittings are of a high quality and the towels were soft. There are no coffee and tea making facilities in the cells but there is a coffee making machine downstairs in the breakfast room, which can be used during the day.

The Black Hole does not have a lift so would not be suitable for someone with mobility issues. The winding staircase is adorned by pictures of criminals in keeping with the theme. On the top floor is a door leading to a sheltered rooftop terrace where there is a great view out towards the city centre with the cathedral visible amongst the trees.
Breakfast is downstairs, a large dresser is home to a coffee making machine, together with a choice of various teas, there are canisters of cereals, small pots of preserves, toast, croissants and yoghurt. There is also the option to have a cooked breakfast if you wish.

Fact Box:
Winchester is easily reached by train from London, with a journey time of just over an hour from London Waterloo Station.
The website for Winchester Tourist Information, Visit Winchester, has extensive information about the city including where to book guided city tours of Winchester
For more to see around Winchester, particularly if you are interested in Jane Austen in Hampshire please check our feature.
Read about my most recent visit for more things to do in Winchester itself.
The Old Vine: https://www.oldvinewinchester.com/
The Royal Oak: https://www.greeneking-pubs.co.uk/pubs/hampshire/royal-oak/
Rick Stein: https://www.rickstein.com/eat-with-us/rick-stein-winchester/
The Chesil Rectory: https://www.chesilrectory.co.uk/
The Black Hole: http://www.theblackholebb.co.uk/
The Black Rat: http://www.theblackrat.co.uk/
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You shared some unique places with us. The black hole interiors with books look so unusual.
I liked the facade of Chesil Rectory. The names are interesting, just for the name’s sake I would like to experience Black Rat 😀
This place brings out the foodie in me.. Not just coz of the good but the Quirky places. Like that whole prison theme. Being a vegetarian, this more than makes up for our limited options
I love England. I haven’t been to Winchester but this looks like a great spot to go and relax after several days of running around London. Love that the Old Vine provides dressing gowns. All the food looks yummy, especially the madeleines with butterscotch sauce
Winchester sounds like a convenient and easy day trip from London. If staying longer the Old Vine Inn looks like a convenient place to stay. With what sounds like a great breakfast.
The narrow passage that The Royal Oak is in looks like something out of Harry Potter!
I used to live in London for a few years and one of the regrets that I have is that I didn’t go and venture out to the English countryside that much. Instead, I just visited some of the more popular cities. Winchester looks like right up my alley, and I’d have loved to stay at The Old Vine Inn. Having stayed at some B&B in old buildings around England, I’m familiar with the fact that the floors slope in places and a bit creaky (and that some have very steep staircase). I guess they add to the charm of the place.
Anyways, thanks for this. Will try to check out Winchester the next time I visit London!
The Chesil Rectory sounds really good. I am a big fan of locally sourced food, lamb and mushrooms. Three out of three works every time. I don’t know about Black Rat or Black Hole. They look lovely, but the names are very interesting.
All of the food looks delicious. I can never say no to a good English breakfast so count me in for a stay at the Old Vine. The Black Rat’s ambience and food also looks great – I appreciate that they serve New Zealand wine.
With Hampshire only being an hour from London, it sounds like it could be just a day trip. But the restaurants and hotel stays might tempt me to make it a longer visit. The Old Vine hotel looks charming. We are seafood fans so would definitely opt to eat at Rick Stein.
This is a great list. I’m also a fan of Rick Stein. I watched plenty of his shows, but i haven’t tried any of his cooking! The Andalucian fritters make my mouth water. The Black Hole bnb sounds like a place I would stay. I love it’s quirky prison-theme interior, and it looks like they stock a lot of book there too!
The food looks amazing! I particularly liked the look of the ham and cheese toastie. Can’t beat it!
Debs