The designated Area of Outstanding Natural Beauty between York and Malton heads the 2020 guide's list of the top 10 locations in the north, beating Alnwick on the Northumberland coast, which took second place.
Beverley, the Leeds suburb of Roundhay, Ripon, Saltaire, the Sheffield neighbourhood of Ranmoor and York are also in the top 10.
The Howardian Hills includes several villages on or near the Castle Howard estate - among them Terrington, Slingsby, Welburn, Gilling, Ampleforth, Hovingham, Crayke, Oldstead and Oswaldkirk - which are known for their attractive period properties. The 79 square miles of countryside offer an easy commute to York and are close to visitor attractions including Castle Howard, Yorkshire Lavender and Eden Camp, as well as the foodie capital of Malton and Michelin-starred gastropub The Black Swan at Oldstead.
The Sunday Times’s expert judges assess a wide range of factors, from schools, transport and broadband speed to culture, green spaces and the health of the high street to produce the definitive guide to the UK's finest locations to call home.
They have travelled thousands of miles around the UK, visiting the locations and talking to locals. They look for improving towns, villages or city centres, for attractive, well-designed homes, and places bursting with community spirit.
The guide also uses robust and exclusive statistics, including up-to-date house prices, provided by mortgage company Habito and TwentyCi.
Roundhay, Ripon and Ranmoor are also newcomers to the guide this year, while Saltaire, Beverley and York have returned for the second consecutive year,
Sheffield's suburbs were omitted from the guide in 2018 following the tree felling scandal, but have now been included again.
Leeds city centre was included in 2019 partly as a result of Channel Four's move north, but it has dropped out of the guide this year, as have Boston Spa, Pateley Bridge and Driffield,
There's also no return for 2018 entries Skipton, Malton, Wetherby and the north Leeds suburb of Chapel Allerton, or 2017 postcodes Helmsley, Hull - which was included during its City of Culture year -, Horsforth, Richmond, Saltburn and Fulwood in Sheffield.
Harrogate has been absent from the guide since 2017, and writers have explained that its high property prices have taken the 'fun' out of the town.
The Sunday Times home editor Helen Davies said: "Never has where you live felt more important. This year we have, along with house prices, air quality, good schools and access to green spaces, championed locations that have showcased great community spirit.
"The feeling of involvement in and concern for one's local community is being challenged - and celebrated - as never before. We wish everyone well wherever they live."
Experts praised the Howardian Hills' 'handsome, mellow stone villages' and access to the market towns of Malton, Thirsk, Helmlsey and Easingwold. Castle Howard is praised for not 'defining' the area despite its significant presence, allowing each village to enjoy its own identity.
Helen added: "The big Yorkshire cities that made it on the list, are all on the up. Business is booming in Leeds; York continues to make the most of its impeccable connections and unrivalled history; while Sheffield has shrugged off the trouble with its trees and is focusing instead on improving its city centre. "
The full in-depth guide is only available to Sunday Times subscribers. View it at sundaytimes.co.uk/bestplacestolive.