Chianti Region Castles from CA $121

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Our top choices for Chianti Region castles

1. Castello Di Montemasso

Greve in Chianti

Quan

CA $188 total

includes taxes & fees

Aug 16 - Aug 17

2. Cattaleya Rooms

Santa Maria Novella

Nicole

CA $121 total

includes taxes & fees

Aug 26 - Aug 27

3. Torre Sassa - Torre Medievale in Toscana

Sassa

Cindylou

CA $1,020 total

includes taxes & fees

Aug 11 - Aug 12

4. 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.

CA $22,790 total

includes taxes & fees

Aug 9 - Aug 10

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Top Chianti Region Hotel Reviews

Hu Norcenni Girasole Village

10/10 Excellent

"Two large pool sites. Helpful staff. Lots of entertainment. Restaurant options and a well stocked reasonably priced food market."

"Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C

10/10 Excellent

"Our family of 18 stayed at the Villa this July (2026) and could not have been more pleased with everything associated with our stay. Jacopo and Beatrice truly are first class hosts. They helped us book 3 vehicles that were dropped off and picked up directly at the Villa which was a great time saver. They also provided a grocery shopping service so that we had drinks and snacks at the villa when we arrived.The meal service was truly fantastic! We opted for the Welcome dinner and the Florentine BBQ, both of which were great. We visited a lot of places while in Italy but the family dinners at sunset were among our favorites.The Villa was beautiful and spacious. The grandkids really enjoyed the open spaces and the pool. The views from the back deck of the surrounding Tuscan countryside were also very special. We even got to see hot air balloons on a few occasions. The relative close proximity to Firenze was also clutch for day trips on high-speed trains. There is a good reason why this Villa won the VRBO Vacation Rental of the Year. You simply cannot go wrong here. I am very thankful for the memories that will last a lifetime and role this villa and the hosts played in making that happen!"

Villa I Barronci Resort & Spa

10/10 Excellent

"This was a fabulous stay. The property is beautiful, the grounds were fun to walk and the swimming pool was lovely. Breakfast every morning was delicious. Hotel was very quiet during the week but was noticeably busier starting Friday (I think local people come just for the weekend). Our room was spacious and very clean. Bed was very comfortable. There is a bar near the pool that serves drinks in the afternoon and dinner nightly on the terrace. The nearby town was so cute and had a coop as well as numerous delicious restaurants (I recommend Nonno’s for a rustic, authentic dinner, La Carboneira for pizzas and I Pini for gelato. I would stay here again and highly recommend!"

Salvadonica - Borgo del Chianti

10/10 Excellent

"This is the Tuscan escape you dream about! We absolutely loved our stay at Salvadonica! A peaceful retreat surrounded by vineyards, hills, and incredible sunsets! It’s perfectly situated to explore Chianti and other locations nearby. The restored farmhouse offers wonderful accommodations that are comfortable and private. There’s a refreshing pool, outdoor movies, yoga in the vineyard, and plenty of spaces to escape and relax. The onsite restaurant La Volpenera, was casually elegant and delicious! Try the gelato with the Salvadonica olive oil…you won’t be sorry. The included breakfast buffet featured a variety of options and was perfect start to each day. We signed up for the Wine and Olive Oil Tasting with Sommelier Irene which gave us a personalized tasting of Salvedonica’s products and history. Excellent experience! And we took the Cooking Class with Chef Ivana which was the best meal we had on our entire trip! Cooking with Ivana felt like we were spending the day with family! Everyone working here provided exceptional service! I only wish we had a longer stay! Can’t wait to return to Salvadonica!"

Villa Il Palagio

10/10 Excellent

"Our family of five enjoyed our time at the property very much. The rooms were comfortable and the surrounding area is beautiful. The pool is a huge plus to cool down and have a relaxing time. The Rignano train station nearby makes it easy to get around Italy, by connecting to Florence’s main station. Truly an asset. The A1 highway is also nearby connecting you within easy access to beautiful Tuscany. Restaurants in the area were very good also. I would definitely stay again at Vila Il Palagio."

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!"

Find out more about Chianti Region

Chianti Region Castles information

Number of reviews	73
Accommodation	34 Castles
Lowest Price	CA $121
Highest Price	CA $22,790

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chianti Region castles

1. Castello Di Montemasso

2. Cattaleya Rooms

3. Torre Sassa - Torre Medievale in Toscana

4. CASTELLO NELLE CRETE

Top Chianti Region Hotel Reviews

Hu Norcenni Girasole Village

"Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C

Castello di Spaltenna- Small Luxury Hotels of the World

Relais Vignale & Spa

Villa I Barronci Resort & Spa

Salvadonica - Borgo del Chianti

Villa Il Palagio

Hotel Villa Campomaggio

Fattoria di Vegi

Find out more about Chianti Region

Chianti Region Castles information

Explore a world of travel with Expedia

Search Castles in Chianti Region from CA $121

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chianti Region castles

1. Castello Di Montemasso

2. Cattaleya Rooms

3. Torre Sassa - Torre Medievale in Toscana

4. CASTELLO NELLE CRETE

Top Chianti Region Hotel Reviews

Hu Norcenni Girasole Village

Find out more about Chianti Region

Chianti Region Castles information

Explore a world of travel with Expedia