I ran across an interesting posting at Good Life Review on this very topic. Check out their point of view on Hotels are for Suckers... Aside from the economic and privacy factors, I'll add one more thing. Staying at a home and opening the front door with your own key, walking in with your groceries with the regions' typical foods, gives the impression that you live in that part of the world, and belong there if only for the length of your vacation. I like that feeling.
For example, this particular gem can be found just outside of Montepulciano...
It so happens that Anne and I were fortunate to find this place while we were on the road. So advance reservations are not always necessary if you are traveling out of season (this was November) or if you are traveling out of the tourist areas (Montepulciano does not qualify for an out of tourist area). There is an ambience that can't be beat, nor can you find at a hotel.
Contact Pina or Andrea (click here for Italian eye candy)
Via di Torrita n 1
Telefono + 39 0578 716277
Fax +39 0578 716277
Cell. +39 339 37.25.762