A stone building with a clock tower, steps leading up to it, and people walking around.

Villas in Castellina in Chianti

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Villas in Castellina in Chianti

A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

A bathroom with a bathtub, shower, and a view of the outside.

A swimming pool with lounge chairs and umbrellas, a brick building with windows, and a clear sky.

A table set outdoors with striped tablecloths, various dishes, glasses, and a decorative rooster.

1. Villa Montecastello

Monteriggioni

$186

$208 total

includes taxes & fees

Oct 24 - Oct 25

See more properties

Top landmarks in Castellina in Chianti

Buondonno Winery

9.6/10 (4 reviews)

Travelers might want a tour of Buondonno Winery, just one of the places to visit, and located 3.9 mi (6.3 km) from central Castellina in Chianti.

See properties

Castellina Fortress

9.4/10 (3 reviews)

If you're planning a bit of sightseeing during your trip, head to Castellina Fortress— just one of the monuments in central Castellina in Chianti.

See properties

Casa Vinicola Luigi Cecchi

9.0/10 (4 reviews)

Travelers might want a tour of Casa Vinicola Luigi Cecchi, just one of the places to visit, and located 5 mi (8 km) from central Castellina in Chianti.

See properties

Lilliano Estate Winery

Travelers might want a tour of Lilliano Estate Winery, just one of the places to visit in the heart of Lilliano.

See properties

Archaeological Museum of Chianti

8.0/10 (6 reviews)

If visiting museums in Castellina in Chianti are on your list, you might want to check out the upcoming exhibitions at Archaeological Museum of Chianti, located in the heart of town. If you want to experience more of the culture Castellina in Chianti has to offer, head to City Hall Castellina In Chianti, Isole e Olena Winery, and Il Molino di Grace Winery.

See properties

Walls of Monteriggioni

9.2/10 (5 reviews)

If museums are on your list of things to see in Castellina in Chianti, then you might want to head to Walls of Monteriggioni. If you want to experience more of the culture Castellina in Chianti has to offer, head to City Hall Castellina In Chianti, Isole e Olena Winery, and Archaeological Museum of Chianti.

See properties

Mazzei Winery

Travelers might want a tour of Mazzei Winery, just one of the places to visit in the heart of Fonterutoli.

See properties

Casina di Cornia Winery

Travelers might want a tour of Casina di Cornia Winery, just one of the places to visit, and located 3.1 mi (4.9 km) from central Castellina in Chianti.

See properties

Learn more about Castellina in Chianti

Notable for its wineries, Castellina in Chianti features attractions such as City Hall Castellina In Chianti and Castellina Fortress. This relaxing city has something for everyone including sights like Archaeological Museum of Chianti and Walls of Monteriggioni within a rural setting.

See all hotels in Castellina in Chianti

About the destination

Castellina in Chianti is a relaxing city where you can spend time checking out the wine tasting. Learn about the local heritage of Castellina in Chianti at landmarks like Castellina Fortress and Walls of Monteriggioni. A stop at other sights like City Hall Castellina In Chianti and Archaeological Museum of Chianti will create memories.