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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Castellina in Chianti villas

Exterior

1. The San Leonino House

The San Leonino House
Castellina in Chianti
The price is ￥124,422
￥243,963 total
includes taxes & fees
Aug 23 - Aug 24
The San Leonino House
Exterior

2. Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills

Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills
Gambassi Terme
The price is ￥749,871
￥750,424 total
includes taxes & fees
Sep 14 - Sep 15
Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills
Exterior

3. Wonderful Villa Pian dei Giullari with Pool – Elegance and Relaxation in the Heart of Florence

Wonderful Villa Pian dei Giullari with Pool – Elegance and Relaxation in the Heart of Florence
Oltrarno
The price is ￥156,776
￥158,988 total
includes taxes & fees
Aug 23 - Aug 24
Wonderful Villa Pian dei Giullari with Pool – Elegance and Relaxation in the Heart of Florence
Property grounds

4. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Toscana
The price is ￥20,277
￥24,148 total
includes taxes & fees
Aug 19 - Aug 20
Rooster House, cooking classes and opera
Villa, Air conditioning, Courtyard View | Exterior

5. Villa Montecastello

Villa Montecastello
Monteriggioni
8.0 out of 10, Very Good, (3 reviews)
"Amazing stay! Teh apartment is HUGE and GORGEOUS. The whole villa is amazing. The view , unbeatable. The host , super warm. Highly recommend!"
United States
Alvaro
The price is ￥29,976
￥33,527 total
includes taxes & fees
Aug 31 - Sep 1
Villa Montecastello
Pool

6. Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Radda in Chianti
10.0 out of 10, Exceptional, (2 reviews)
"A dream property come true. Breathtaking views, most accommodating hosts, Perfect Tuscan location."
United States
Amber M.
The price is ￥178,041
￥266,684 total
includes taxes & fees
Sep 1 - Sep 2
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Property grounds

7. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Siena
The price is ￥800,453
￥892,620 total
includes taxes & fees
Aug 18 - Aug 19
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Property grounds

8. "Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi

"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
Gaiole in Chianti
10.0 out of 10, Exceptional, (9 reviews)
"Best view in TuscanyIt was all new on the inside and very rustic exterior Beautiful villa!!!Great Host "
United States
Bernard K.
The price is ￥248,851
￥253,275 total
includes taxes & fees
Aug 22 - Aug 23
"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
Exterior

9. Villa Il Signorino

Villa Il Signorino
GREVE IN CHIANTI
9.4 out of 10, Exceptional, (3 reviews)
"Nice place 👌 "
United States
Avi A.
The price is ￥64,517
￥91,061 total
includes taxes & fees
Sep 1 - Sep 2
Villa Il Signorino
Property grounds

10. Villino Tre Pini | Panoramic Private Pool, Nature & Privacy

Villino Tre Pini | Panoramic Private Pool, Nature & Privacy
Toscana
10.0 out of 10, Exceptional, (1 review)
The price is ￥66,360
￥167,190 total
includes taxes & fees
Aug 27 - Aug 28
Villino Tre Pini | Panoramic Private Pool, Nature & Privacy
Exterior

11. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is ￥316,317
￥357,055 total
includes taxes & fees
Aug 30 - Aug 31
Villa Torre Among the Hills of Siena
Exterior

12. Villa "Arnilù" with Private Pool & Wi-Fi

Villa "Arnilù" with Private Pool & Wi-Fi
San Gimignano
The price is ￥910,432
￥978,794 total
includes taxes & fees
Aug 18 - Aug 19
Villa "Arnilù" with Private Pool & Wi-Fi
Property grounds

13. Villa Capannina with Private Pool, Wi-Fi and Air Conditioning

Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
Vico dʼArbia
10.0 out of 10, Exceptional, (1 review)
"Lovely house in the Montechiaro property, very close to Siena, but far enough to enjoy the night sky in Tuscany. Communication was great."
United States
Marina O.
The price is ￥197,090
￥237,828 total
includes taxes & fees
Aug 24 - Aug 25
Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
Outdoor dining

14. Villa Mami: A Tuscan Retreat of Elegance and Charm

Villa Mami: A Tuscan Retreat of Elegance and Charm
Toscana
10.0 out of 10, Exceptional, (1 review)
The price is ￥645,170
￥799,089 total
includes taxes & fees
Sep 9 - Sep 10
Villa Mami: A Tuscan Retreat of Elegance and Charm
Terrace/patio

15. Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany

Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
Certaldo - Firenze
2.0 out of 10, (1 review)
"House is very nice and clean , but not equipped for rental, kitchen is poorly equipped, towels are like napkins , no toilet paper, no soap , nothing "
United States
Kelly C.
The price is ￥86,998
￥109,479 total
includes taxes & fees
Aug 18 - Aug 19
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
Outdoor dining

16. Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (149 reviews)
"This was everything that it promised! The property is amazing. David was a great host and having his sister right next door was a godsend. She was very helpful with tips of places to go and ideas of how to get there. She even helped us order a taxi one morning. We had a fantastic time! It is definitely worth the visit!"
United States
Dawn L.
The price is ￥46,084
￥69,126 total
includes taxes & fees
Aug 29 - Aug 30
Luxury Villa in the Florentine hills
Exterior

17. Nice apartment in villa with A/C, pool, WIFI, TV, terrace and panoramic view, close to San Gimig...

Nice apartment in villa with A/C, pool, WIFI, TV, terrace and panoramic view, close to San Gimig...
Montaione
10.0 out of 10, Exceptional, (5 reviews)
"We spend a great time, marvellous place and people"
United States
Carole G.
The price is ￥26,544
￥30,282 total
includes taxes & fees
Aug 19 - Aug 20
Nice apartment in villa with A/C, pool, WIFI, TV, terrace and panoramic view, close to San Gimig...
Outdoor dining

18. Villa 'Molino' with Private Pool, Private Terrace and Wi-Fi

Villa 'Molino' with Private Pool, Private Terrace and Wi-Fi
Mercatale Val Di Pesa
The price is ￥254,921
￥255,658 total
includes taxes & fees
Aug 23 - Aug 24
Villa 'Molino' with Private Pool, Private Terrace and Wi-Fi
Exterior

19. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
The price is ￥2,401,358
￥2,401,358 total
includes taxes & fees
Aug 18 - Aug 19
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Outdoor dining

20. Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~

Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Impruneta
10.0 out of 10, Exceptional, (3 reviews)
"Super quaint, beatiful, designed, comfortable, not lacking anything house and location. Very informative and accessable host. Listen to the instructions on how to go to Firenze. No need to take your car tyere!"
United States
Maria H.
The price is ￥47,429
￥65,125 total
includes taxes & fees
Aug 18 - Aug 19
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
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 Castellina in Chianti Hotel Reviews

Hotel Calimala Florence

Hotel Calimala Florence

10/10 Excellent
"Loved Calimata in Florence I stayed in the one in Milano. Staff fabulous breakfast choice are many. Precious made the BEST cappuccinos. I'm down for 3 a day at breakfast. LOVED the rooftop too."
Angela 3-night trip
Posted 2 hours ago
Hotel Calimala Florence

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Number of reviews
176
Accommodation
1879 Villas
Lowest Price
￥24,148
Highest Price
￥2,401,358

Frequently asked questions

How much do villas in Castellina in Chianti cost?
Villas in Castellina in Chianti range between ￥24,148 and ￥2,401,358 per night. These stays offer the privacy of your own space at a price that doesn't break the bank. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in Castellina in Chianti?
You can choose from 1879 villas in Castellina in Chianti. No matter if you're traveling with the family or planning a getaway with your buddies, Expedia will help you find the ideal base for your squad.
Why book your villa in Castellina in Chianti with Expedia?
Reserving a villa in Castellina in Chianti is as simple as deciding on your travel dates and picking the option suited to your needs. In search of something affordable or luxurious, or a property that also has a kitchen and laundry? Use Expedia's search filters to narrow your results and find the perfect pad.
How can I find cheap villas in Castellina in Chianti?
The easiest way to compare cheap villas in Castellina in Chianti is with Expedia's convenient filter tool. Narrow your search by amenities, budget and star rating to nab awesome rates in only a few clicks.
What is there to do near my villa in Castellina in Chianti?
Whatever your interests, Castellina in Chianti has loads to keep you on the hop. Buondonno Winery, City Hall Castellina In Chianti and Casa Vinicola Luigi Cecchi are on most visitors' itineraries. Don't forget to explore Walls of Monteriggioni, Castellina Fortress and Archaeological Museum of Chianti either. With Expedia's Castellina in Chianti hotel deals, you can discover even more terrific attractions like these with the cash you save.