Let KAYAK do the searching
Based on KAYAK hotel searches, the most popular destination is Florence (95% of total searches to Chianti). The next most popular destinations are Siena (3%) and Montepulciano (1%). Searches for hotels in San Gimignano (1%) are also popular.
KAYAK users have found double rooms in Chianti for as cheap as $36 (Peccioli) in the last 3 days. The average price is $425.