A vineyard with rows of grapevines, a house surrounded by trees, and a road with vehicles.

Chianti Region Castle Hotels

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Check prices for these dates

Next weekend
Aug 21 - Aug 23
In two weeks
Aug 28 - Aug 30
In one month
Sep 11 - Sep 13
In two months
Oct 9 - Oct 11

Our top choices for Chianti Region castles

Aerial view

1. Castello Di Montemasso

Castello Di Montemasso
Greve in Chianti
9.8 out of 10, Exceptional, (23 reviews)
"The Castello Di Montemasso is a beautiful place with nice staffs. Their breakfast is awesome."
United States
Quan
$122 nightly
The price is $135
Sep 6 - Sep 7
Total with taxes and fees
Castello Di Montemasso
Standard Triple Room | Hypo-allergenic bedding available, down comforters, desk, soundproofing

2. Cattaleya Rooms

Cattaleya Rooms
Santa Maria Novella
8.4 out of 10, Very Good, (50 reviews)
"Close to station and basic amenities and property well maintained and clean"
Canada
Vishnu
$65 nightly
The price is $86
Aug 26 - Aug 27
Total with taxes and fees
Cattaleya Rooms
Exterior

3. CASTELLO NELLE CRETE

CASTELLO NELLE CRETE
Siena
10.0 out of 10, Exceptional, (1 review)
"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...
United States
joanne s.
$16,329 nightly
The price is $16,329
Aug 17 - Aug 18
Total with taxes and fees
CASTELLO NELLE CRETE
Exterior detail

4. Torre Sassa - Torre Medievale in Toscana

Torre Sassa - Torre Medievale in Toscana
Sassa
10.0 out of 10, Exceptional, (1 review)
"This tower was absolutely beautiful, spacious and clean. The medieval decor was awesome. Stefania came in to cook and it was absolutely amazing and delicious. We left some items behind and Giacomo contacted us promptly and is shipping the items back home to us. An absolutely wonderful experience!!"
Canada
Cindylou
$727 nightly
The price is $730
Aug 22 - Aug 23
Total with taxes and fees
Torre Sassa - Torre Medievale in Toscana
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chianti Region Hotel Reviews

Villa Casagrande Resort & SPA

Villa Casagrande Resort & SPA

10/10 Excellent
"What a wonderful 3 night break at Villa Casagrande! My wife and I had a beautiful stay in this historic villa. There’s a little steep walk up to the pool and restaurant next to it which were perfect and where we spent most of our time relaxing and sunbathing with the view of the trees and the Tuscan mountains. The staff were incredible, so kind, quick to help and made our stay even more pleasant. We both had lovely massages and relaxed in the spa area and one evening did the historic tour and wine tasting which was exceptional. The guides and sommeliers were so knowledgeable and so lovely and the organic Chianti wines they produce are an absolute must to taste and buy. The hotel’s main restaurant was the best in Filigne (the local town) and the food was incredible. One of the nights we had a live musician who was fantastic. We had dinner twice there; mushroom tagliatelle, the lamb, the wild boar gnocchi and paccheri carbonara were to die for! It’s only 50 mins on the train to Florence which is one of our favourite cities to explore in one day and we picked this place especially because it’s only a 12 minute walk from the Filigne Valdarno station and avoids the need to hire a car. We went for the comfort room which was spacious and clean and the air con was great and important for us it had a powerful shower. We truly had a wonderful time and absolutely cannot wait to go back next year! Grazie Villa Casagrande!"
C 3-night trip
Posted 2 days ago
Villa Casagrande Resort & SPA

Find out more about Chianti Region

Chianti Region Castles information

Number of reviews
75
Accommodation
30 Castles
Lowest Price
$86
Highest Price
$16,329

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