Chianti Region Castles With Overnight Rooms from $96| Expedia

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

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Our top choices for Chianti Region castles

Castello Di Montemasso

Greve in Chianti

Quan

$121 nightly

Jul 26 - Jul 27

Total with taxes and fees

Standard Triple Room | Hypo-allergenic bedding available, down comforters, desk, soundproofing

Cattaleya Rooms

Santa Maria Novella

Nicole

$75 nightly

Aug 16 - Aug 17

Total with taxes and fees

Torre Sassa - Torre Medievale in Toscana

Sassa

Cindylou

$720 nightly

Jul 18 - Jul 19

Total with taxes and fees

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.

$16,149 nightly

Jul 18 - Jul 19

Total with taxes and fees

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Top Chianti Region Hotel Reviews

Castello Vicchiomaggio

10/10 Excellent

"A true oasis in Tuscany, large rooms with every needed amenity, fantastic pool overlooking the vineyards"

Villa I Barronci Resort & Spa

10/10 Excellent

"An amazing place to stay and relax in Florence. Highly recommend if you want a place to relax and away from the crowds . The staff was very respectful, polite and accommodating. Breakfast was amazing especially the chocolate croissants. Great value for the price. Thank you villa I Barronci!"

Villa Sabolini

10/10 Excellent

"We came to this hotel unexpectedly and were so happy we found it. The staff are truly exceptional, friendly, attentive, accommodating, effective, welcoming. We arrived due to my wife having emergency surgery in Siena, we were supposed to be in Venice, and this hotel staff went to work making sure we were taken care of. The grounds are stunning as well, an amazing place to recover after surgery. The pool is beautiful and the restaurant is fantastic. I truly have enjoyed each meal I have had. The lunch I ordered of sliced beef with rocket, pecorino and tomato was perfectly cooked and so tasty. The bartender Bruno makes a fantastic Negroni and I have had the chance to taste it with 3 different small gins all from this region. The front office staff from Silvia, Valentina and each person we interacted with have been amazing. We were looking forward to the basset hounds as well, we have seen them lounging about but hope to get to meet them before our stay ends. A wonderful place to stay in the Tuscan countryside, and only a 20 minute drive to Siena."

Hotel Villa Campomaggio

10/10 Excellent

"I was fortunate enough to stay in this beautiful hotel whilst photographing a wedding in Tuscany and I was so pleased that I am hoping to stay again as soon as I can. The staff were lovely, the hotel was beautiful and the surrounding areas were stunning. The spa was clean and calming, with three different rooms to try and a jacuzzi. I was offered a free yoga class one morning and my room was cleaned before 10am every day. On my last day, I checked out at 11am after breakfast and was offered a place to keep my bags so that I could stay out by the pooI until I needed to leave. I would highly recommend this beautiful hotel to anyone travelling through Tuscany!"

Villa "Torre in Chianti", 8 ensuite bedrooms,A/C, Private Pool, WiFi, Florence

10/10 Excellent

"Our hosts and the property lived up to all our expectations! Communication with Beatrice and Jacopo was excellent. This was especially important as we planned this trip ourselves. When we arrived, they were so welcoming. They made us feel at home. This was the perfect Tuscan experience for our family. We were 3 generations and the villa was just what we needed. The pool was a welcome respite after our days out. The kitchen was equipped with everything we needed for the days we chose to cook. But, the best meals of our trip were those cooked by Beatrice and Jacopo! We had breakfast and dinner prepared by them. An abundance of food! Don’t miss out on this! And don’t scroll past this property. Book it and you will be in for a treat!"

Find out more about Chianti Region

Chianti Region Castles information

Number of reviews	70
Accommodation	36 Castles
Lowest Price	$96
Highest Price	$16,149

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Upfront pricing

Check prices for these dates

Our top choices for Chianti Region castles

Castello Di Montemasso

Cattaleya Rooms

Torre Sassa - Torre Medievale in Toscana

CASTELLO NELLE CRETE

Top Chianti Region Hotel Reviews

Castello Vicchiomaggio

Villa I Barronci Resort & Spa

Castello di Spaltenna- Small Luxury Hotels of the World

Relais Vignale & Spa

Salvadonica - Borgo del Chianti

Villa Sabolini

Hotel Villa Campomaggio

Villa "Torre in Chianti", 8 ensuite bedrooms,A/C, Private Pool, WiFi, Florence

Fattoria di Vegi

Find out more about Chianti Region

Chianti Region Castles information

Explore a world of travel with Expedia

Chianti Region Castle Hotels

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Chianti Region castles

Castello Di Montemasso

Cattaleya Rooms

Torre Sassa - Torre Medievale in Toscana

CASTELLO NELLE CRETE

Top Chianti Region Hotel Reviews

Castello Vicchiomaggio

Find out more about Chianti Region

Chianti Region Castles information

Explore a world of travel with Expedia