The usual tile rendering software is Mapnik , and there is a Windows version of that. Installation instructions here: http://trac.mapnik.org/wiki/WindowsInstallation
You will also need the PostgreSQL / PostGIS database, and osm2psql, which it seems there’s a Windows version of.
So it should all be possible. Though setting this up might be a bit complicated. I don’t know if there’s any good guides anywhere.
To generate tiles on the fly, I think you can use renderd and mod_tile (an Apache module). http://wiki.openstreetmap.org/wiki/Mod_tile
Though I’ve never used this, so I’m not sure how it works, or whether there is a Windows version. You may have to compile it yourself.