Winchester Holidays – Accommodation and Places to Stay in Winchester I Cool Places


Handsome and historic, friendly yet refined, Winchester packs a potent punch of ancient monuments and contemporary culture – a place where grand old buildings mingle with 21st-century sculpture and where medieval taverns and pubs make characterful and tempting stopoffs, with many a traditional boozer (or two) to try along the way. Castle, college and cathedral might be the first stops on any itinerary, but there’s just as much to enjoy in just ambling about – browsing backstreet bookshops, idling over a coffee and wandering through the water meadows, which is just a taster of the rich rolling countryside that surrounds the city on all sides. Bearing in mind all of these features, Winchester makes a tremendous place for a weekend break, with a number of appealing places to stay, both in the city itself and in the bucolic Hampshire. countryside beyond, not to mention a range of gastropubs and restaurants that turn out some of the region’s best Modern British cuisine.

Search near your current location

We won't store your location, we'll only use it to find places to stay near you

Choose check in and check out dates  

We are limiting availability in line with the Coronavirus restrictions in each country, and we will update this as guidance changes.

Check In Available Unavailable
previous month next month
show more months

How many adults and children are in your party? Please provide an age for each child for an accurate price.





Best Places to Stay in Winchester

Showing 1 - 5 of 5

Loading map

Eat and Drink

When it comes to food and drink Winchester has a fantastic selection on offer. A spattering of friendly pubs can be found, that have been doing business for years and know a thing or two about how to serve fine beer with hearty food. During the day time there are also a handful of cafes and delis which, offer light bites and lunches to keep a weary visitor well fuelled, but if its takeaway food your after its best to head to the countries biggest Farmers Market, taking place on the second and last Sunday of each month. Winchester can also boast fine dining, with a range of cuisines including Asian, Spanish and French, as well as a Michelin Star restaurant - The Black Rat. For a more lively evening there are a couple of good bars in town offering cocktails and live music.


The size of Winchester's compact city centre makes it a desirable place to do a little shopping and, once past the streams of traffic on the central 'city road', you can relax in smaller lanes peppered with interesting shops. The hub of the shopping is in pedestrianised streets near to the cathedral and around the market square which plays host to an award winning farmers market, the largest in the country. This is a great place to buy local produce and a must-see amongst your browsing of the nearby retailers. Winchester boasts a diverse range of independent shops, with arts, crafts and antiques to be found, as well as trendy home wares in the grand Georgian setting of The Hambledon department store.

Things to Do

The chief attraction in this secluded old city is the magnificent cathedral, at almost a thousand years old, it is well worth a visit not only for its stunning medieval architecture but also the treasure trove of historic artefacts within. The cathedral is complimented by similarly ancient college buildings and a couple of museums to tell the tales of England's one-time capital. Winchester also makes a good base for exploring other historic sites, with the villages of Alton, Chawton and Selbourne within a 15 mile radius, each with points of interests such as the fifteenth-century Church of St Lawrence in Alton and the former home of Jane Austen in Chawton. There are numerous pleasant walks to be had, both within the city but also beyond, with The South Downs and The New Forest within easy driving distance. Amongst the age and prestige of this charming city you will also find the strikingly modern INTECH science museum, with hands on interactive activities and regularly changing exhibitions.

What Customers say about Cool Places

Love the website

Love the website and how it has all the different sections, making it easy to find just what you’re looking for. Definitely recommending to friends and family.

Lexy, Verified Customer

I will definitely use it again

This is the first time I've used Cool Places and I will definitely use it again for the best places to stay.

Karin, Verified Customer

Easy to use

Easy to use and some amazing properties to choose from.

Helen W, Verified Customer

So many beautiful places to stay

The website is really easy to use and includes so many beautiful places to stay. I found the destination guides really helpful when looking for my next staycation.

Lauren, Verified Customer

Great website, very user-friendly

Great website, very user-friendly. There are so many fantastic places to stay. My wish list is ever growing!

Kelly, Verified Customer