Stayed in a small village in Val d'Orcia, population was less than 300 people in 2011. I can't recommend it enough, especially compared to touristy and busy towns like Siena. [enter link description here][1]
The town is called Castelmuzio, it's a 10-15 minute drive to Pienza. Very quiet and relaxing medieval walled village in Tuscany's Val d'Orcia region. Not a lot to do in the evenings, only one restaurant in Castelmuzio and one right outside of town in a hotel. So maybe not for everyone if you prefer having lots of restaurant options and more people nearby, but perfect if you're looking for somewhere peaceful.
Explored nearby Pienza, Montepulciano and Montalcino and checked out some of the local wineries. Excellent wines in this region, Brunello di Montalcino, Rosso di Montalcino, Vino Nobile di Montepulciano. Still have more I'd like to do in Val d'Orcia if I'm able to return someday. Would absolutely stay in Castelmuzio again.