My father sagely pointed out that, having never stayed in a Montalcino hotel, I am scarcely in a position to recommend them and of course he is right. I must also admit that I know the proprietors since everyone knows everyone in Montalcino. I will add that I have only heard good things about the following establishments from people who have stayed there.

Provisoes made, here are some places to stay in and out of town.

http://www.gigliohotel.com/en/

This three star hotel is on the main street in Montalcino. For a room with a view you can’t do much better. The hotel has a fine-dining restaurant with wonderful tasting menu options and, important in a medieval town, parking is provided for clients.

For the comfort of a really sumptuous bed and breakfast, try Palazzina Cesira http://www.montalcinoitaly.com/home_cesira.htm on the main street in Montalcino. The beds are (apparently) as big as tennis courts and they do a lovely breakfast. There are renaissance frescoes in the bedrooms and an American owner...

 Another wonderful B&B option is http://www.portacastellana.it/eng/home_en.html, hidden away in the backstreets of town where many Montalcinesi never set foot. There are only two rooms so it is extremely personal, you can have breakfast outside overlooking the Val D’Orcia. Free parking is provided.

http://www.suiteintuscany.it/aboutus.php There are four suites tucked away in Montalcino’s backstreets. They are beautifully decorated and each features work from a different modern artist. Luxurious and private, they can be enjoyed for long-term rents or short stays.

http://www.santemarie.it/home_eng.htm

This is a tiny winery and is organised in a very careful and personal way. The wines are fabulous. It is just below Montalcino - in walking distance from town (20 mins uphill!). There are three self-catering mini apartments.

http://www.le7camicie.it/en/to-sleep-in-agritourism-le7camicie.html

This agriturismo is just beyond Castelnuovo dell’Abate, a village 7km from Montalcino where the beautiful Romanesque abbey of S.Antimo is located. There are apartments for 2, 4, 6, 8, 10 and 12 people. A panoramic natural hot water bath (around 40 °C) is open every day and night of the year and a summer swimming pool is available from June to October. The views are extraordinary.