Let KAYAK do the searching
Based on KAYAK hotel searches, the most popular destination is Florence (96% of total searches to Chianti). The next most popular destinations are Siena (3%) and Montepulciano (1%). Searches for hotels in Arezzo (0%) are also popular.
KAYAK users have found double rooms in Chianti for as cheap as $61 (Florence) in the last 3 days. The average price is $627.