Il Tosco is the perfect combination of an Air BNB and Luxury Hotel. With only four rooms in this stately residence, you feel like Elena's guest. You have kitchen and all living space access (amazing pastries baked by Mom, coffee etc,), but can retreat to your modern room for privacy. Breakfasts are a feast with excellent coffee, fresh pastries and eggs cooked to order, if you want. Elena will bring your luggage to your room, and deliver it back to your car. She will also make restaurant, sights and winery recommendations, and will even book a reservation for you. She can arrange to ship your wine purchases home for you. The only negative for us would be spotty wifi in our particular room; however we had enough access for someone on vacation!
Montepulcianco is a charming walled city with great walking, shopping and food. It was a perfect home base for us.