I would suggest you look at Heroic B&B experiences in Rick Steves' Graffiti Wall. Many names come up time and time again with great recommendations.
Other sources of rooms are Booking.com, AirBnB.com, Agriturismo.com and Venere.com. You can also sign into Craigslist.com and find agriturismo rooms overseas.
If you can figure out which town you'd care to stay close to, you can go on GoogleMaps, put in the city/country and hit enter. Then hit the "+" twice to magnify the map, and many, many hotels and B&B's will pop up all over the place.
The farms throughout Tuscany and Chianti have apartments and rooms as a great source of secondary income. Virtually every farm in some areas are agriturismos.
Last year, we stayed in Florence for a long weekend, and moved to between Certaldo and San Gimignano for 4 nights. It's a great area to do day trips to Siena, San Gimignano and Volterra. We found huge supermarkets in Poggibonsi, and did most of our own cooking at night. We turned our rental car in at Orvieto and caught a train into Rome.