I'll pull together a longer reply when I've time as we've checked out a phenomenal number of places now over the course of the last 18 months.
The area has great cities (Manchester, Liverpool and Chester) and plenty of picturesque small villages (pub, primary, shop type places) but Cheshire isn't great for attractive large villages/small towns which is what we'd ideally move into (Knutsford and Tarporley being our favourite 'small town' and 'large village' respectively).
I do like Bollington (pretty good facilities, good number of pubs, good primaries, good walks (canals, access across to Goyt valley, Peaks etc), good community, mainline rail a short drive away in Macc). Downsides - secondary school it's in catchment for is ok but not the best in the area, nearest 'bigger' place is Macc - nothing wrong with it but nothing to go dreamy about either. You're a bit of a hike to Manchester (largest nearby centre).
What do you want your village to have?
- pub (or two)?
- shop (or more)?
- primary (secular or CoE)?
- bus route to nearest centre?
- train line to nearest centre?
- more facilities beyond village shop/pub, e.g. restaurants, PO, hairdresser, butcher, grocer, bank, library, secondary school?
If you like Winchester then you'd feel at home taking trips out into Chester or Knutsford (smaller). They're the closest to Winchester in terms of being attractive shopping centres. When you consider options, be conservative around journey to work estimates - some busy roads/motorway junctions near the airport/coming into Manchester.
Sorry, just saw you said you only need a pub and school! Lots of options then. Think about where you'd like access to beyond the airport (M6, Manchester, Chester, mainline rail south etc)