just to tell you, the closest you're going to get is :
ludlow
lavenham
york
conwy
culross is also worth a look, though it's more 17th/18th century
edit; forgot stratford-upon avon
many of the buildings that survive look medieval, but are in fact late medieval or renaissance
Chester
Winchester
Farnham
Portchester
I suppose it depends on what you consider medieval, and how what the criteria is for "closest".
Southampton has a virtually intact medieval merchant's house. Many places still have ancient walls (Portchesters are Roman, so predate the Norman Castle by 100s of years)
winchester doesn't really have that much surviving medieval/renaissance infrastructure to warrant it being called medieval, tbh. nor does portchester or the other places.
a lot of the buildings in chester are mock-tudor
It depends on your definitions - how many buildings/what proportion of buildings, time periods etc. you wish to include.
If you take the definition of Medieval to be from around 500AD up to 1500AD then in Winchester you can include the cathedral, the great hall, Winchester college, the city mill (although this was largely rebuilt in the 1700s), Chessil rectory, Godbegot hall, several churches and the old St Cross hospital/monastery. That should keep anybody busy for most of a day.
There are medieval castles all over Britain. In fact, the most concentration of castles are in Wales.
The Normans built churches all over the country after taking over in 1066. Some of the most amazing Cathedrals are in Winchester, Salisbury, Canterbury, York, Durham, London and more. Oxford and Cambridge are Universities worth a visit. Scotland has Edinburgh and more.
And you know this how?
i know this from research
In most towns and villages in England, the church was built in the period 1100-1300. At that time it would be the only stone building, the houses would be wooden thatch straw huts. It was another few centuries before the Lord of the Manor could afford brick (tudor manor houses, ~1500 onwards, no longer classed as medieval). The poor still couldn't afford brick for a few more centuries.
Most churches have been enlarged over the centuries, but any village with any claim to history has a medieval church.
Here is the one in the town I grew up in (click for photo): "The present church stands on the site of two previous churches and dates from the 14th and 15th centuries, with its tower dating from around 1190." - Is that medieval enough for you?
Point is, it is difficult to find a town or villages in England that hasn't got something medieval.
How about Canterbury?
Add Wells to your list...
A bit of an odd, unsolicited post. Any particular reason other than "I've done a bit of research"?
Ditto JC’s comment.
shrewsbury is also, good. salisbury is a beautiful town, also, with some medieval history.
Romsey Abbey (close to Winchester, Southampton and the New Forest) certainly qualifies. The Abbey Church can trace its origins back to 907 AD. The first stone church and nunnery were built c. 1000 AD. Work began on the present building c. 1120-1140. Arches were added in 1230-1240:
https://www.romseyabbey.org.uk/about/history/
Nearby you'll find King John’s House, a 13th-century merchant’s house:
http://kingjohnshouse.org.uk/
The oldest pub in Romsey, is too young however, only dating in part from the 17th Century,
http://www.theoldhouseathomeromsey.co.uk/
But Southampton boasts one of the oldest pubs in England: The Red Lion.
http://sotonopedia.wikidot.com/page-browse:red-lion-public-house
https://www.dailyecho.co.uk/leisure/pubs/13350401.the-red-lion-high-street-southampton/
southampton is depressing and very brutalist, has a few nice buildings though.
