Castellina in Chianti Castles With Overnight Rooms from $116| Expedia

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

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Our top choices for Castellina in Chianti castles

An aerial view of a large, rectangular building with a central courtyard, surrounded by a curved road and sparse vegetation.

1. Castello Di Montemasso

Greve in Chianti

Quan

$104 nightly

Oct 25 - Oct 26

Total with taxes and fees

An aerial view of a villa with a swimming pool, surrounded by trees and a lake.

2. CASTELLO NELLE CRETE

Siena

"Picture yourself in a century-old castle high on a hill in the heart of Tuscany. Your surroundings are those of a majestic Monet painting. Birds humming, and the smell of fresh croissants fills the air. A cup of hot cappucino is being brought to you by the most professional but always smiling and always friendly staff .No you're not dreaming, you and your family of 30 are guests at Villa Leonina, Every room has an ensuite bathroom with daily maintenance and fresh towels. The kitchen and...

joanne s.

$16,076 nightly

Sep 29 - Sep 30

Total with taxes and fees

A modern bedroom with a bed, wardrobe, and a mirror.

3. Cattaleya Rooms

Santa Maria Novella

Vishnu

$105 nightly

Oct 28 - Oct 29

Total with taxes and fees

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Top Castellina in Chianti Hotel Reviews

Grand Hotel Cavour

10/10 Excellent

"Beautifully appointed hotel with an exceptional staff."

The Social Hub Florence Lavagnini

8/10 Good

"The property is definitely a unique property I didn’t realize prior to booking that it caters to student accommodation which is fine I believe students from USC were checking in same time as the Stanford students were leaving I enjoyed the property my only reason for giving 4 out of five stars was my room was like a dorm room very small bed was not comfortable. But I really liked the property the staff were all helpful and professional."

Hotel Horto Convento

10/10 Excellent

"Absolutely amazing hotel. Beautiful grounds and building in a nice, quiet part of the neighborhood, but still so walkable and close to churches, museums, restaurants, etc. Cherish at check-in gave us some great recommendations for food nearby. Had some of the best baked goods I've ever had at breakfast each morning, and had the most beautiful and delicious cocktails and spritz from the bar in the evening. If we come back to the city, we'd 100% want to stay here again."