San Francisco, From $108 a Night
This festive hotel package is valid over the holidays and includes ice-skating at Union Square.
RADDA IN CHIANTI
Le Cannelle sleeps six, from $1,520 per week, available through Italian Vacation Villas, 202/333-6247, villasitalia.com. Photos 1 of 2
• Villa owners recommend: Bar Dante
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GAIOLE IN CHIANTI
Le Miccine sleeps six, from $2,475 per week, available through Home Away, 512/493-0382, homeaway.com. Photos 1 of 4
• Villa owners recommend: Ristoro di Lamole
LUCCA
Il Mezzanino sleeps five, $2,500 per week, available through Ville et Village, 510/559-8080, villeetvillage.com. Photos 1 of 3
• Villa owners recommend: Buca di Sant'Antonio
CASTELLINA IN CHIANTI
La Fontanella sleeps eight, from $3,025 per week, available through Italian Vacation Villas, 202/333-6247, villasitalia.com. Photos 1 of 3
• Villa owners recommend: Ristorante di Pietrafitta
CORTONA
La Pietra sleeps six, from $3,480 per week, available through Italian Vacation Villas, 202/333-6247, villasitalia.com. Photos 1 of 5
• Villa owners recommend: Trattoria Dardano
Above we've listed the nearest town within a 10-mile radius of each villa.