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

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Check prices for these dates

In two weeks
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Castellina in Chianti villas

Exterior

1. The San Leonino House

The San Leonino House
Castellina in Chianti
The price is SAR 2,956
SAR 5,796 total
includes taxes & fees
27 Aug - 28 Aug
The San Leonino House
Pool

2. 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 SAR 2,350
SAR 4,456 total
includes taxes & fees
17 Sep - 18 Sep
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Property grounds

3. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Toscana
The price is SAR 482
SAR 574 total
includes taxes & fees
1 Sep - 2 Sep
Rooster House, cooking classes and opera
Villa, Air conditioning, Courtyard View | Exterior

4. 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 SAR 690
SAR 772 total
includes taxes & fees
29 Aug - 30 Aug
Villa Montecastello
Property grounds

5. "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 SAR 6,598
SAR 6,703 total
includes taxes & fees
11 Sep - 12 Sep
"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
Exterior

6. 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 SAR 1,380
SAR 1,993 total
includes taxes & fees
1 Sep - 2 Sep
Villa Il Signorino
Property grounds

7. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Siena
The price is SAR 19,018
SAR 21,208 total
includes taxes & fees
27 Aug - 28 Aug
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Outdoor dining

8. Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
The price is SAR 6,771
SAR 7,740 total
includes taxes & fees
30 Aug - 31 Aug
Villa Capanna: A Window onto Tuscany
Exterior

9. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is SAR 6,764
SAR 7,732 total
includes taxes & fees
30 Aug - 31 Aug
Villa Torre Among the Hills of Siena
Outdoor dining

10. 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 SAR 876
SAR 1,467 total
includes taxes & fees
29 Aug - 30 Aug
Luxury Villa in the Florentine hills
Exterior

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

Villa "Arnilù" with Private Pool & Wi-Fi
San Gimignano
The price is SAR 24,059
SAR 25,685 total
includes taxes & fees
21 Sep - 22 Sep
Villa "Arnilù" with Private Pool & Wi-Fi
Outdoor dining

12. Villa Bellavista - Homelike Villas

Villa Bellavista - Homelike Villas
Montegonzi
Villa Bellavista - Homelike Villas
Exterior

13. Lovely apartment in villa with A/C, WIFI, pool, TV, terrace, panoramic view, close to San Gimignano

Lovely apartment in villa with A/C, WIFI, pool, TV, terrace, panoramic view, close to San Gimignano
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 SAR 631
SAR 720 total
includes taxes & fees
28 Aug - 29 Aug
Lovely apartment in villa with A/C, WIFI, pool, TV, terrace, panoramic view, close to San Gimignano
Exterior

14. 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 SAR 17,834
SAR 17,847 total
includes taxes & fees
19 Sep - 20 Sep
Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills
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 SAR 2,067
SAR 2,601 total
includes taxes & fees
30 Aug - 31 Aug
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
Outdoor dining

16. 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 SAR 6,063
SAR 6,081 total
includes taxes & fees
29 Aug - 30 Aug
Villa 'Molino' with Private Pool, Private Terrace and Wi-Fi
Outdoor dining

17. 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 SAR 1,127
SAR 1,547 total
includes taxes & fees
28 Aug - 29 Aug
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Outdoor pool

18. Villa Sunset, in the heart of Chianti

Villa Sunset, in the heart of Chianti
Greve in Chianti
8.0 out of 10, Very Good, (1 review)
"La casa é spaziosa ed accogliente e molto pulita in una posizione e strategica e comoda per visitare Firenze e i borghi della zona. "
Italy
elisa b.
Villa Sunset, in the heart of Chianti
Outdoor dining

19. Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi

Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi
Gaiole in Chianti
8.0 out of 10, Very Good, (1 review)
"Pros: La casa è sita in una posizione super tranquilla in mezzo al verde e alla natura. Tutto è curato alla perfezione. Nota di merito per il verde e i fiori e per la gentilezza dei proprietari. Cons: La posizione che è un pregio per qualcuno per altri potrebbe non esserlo. In effetti per arrivare al podere ci sono 2 km di strada bianca molto stretta. Una volta arrivati si è però ripagati ampiamente del piccolo disagio!"
Italy
Anonymous traveler
The price is SAR 4,201
SAR 5,020 total
includes taxes & fees
1 Sep - 2 Sep
Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi
Exterior

20. Villa Milani with Shared Pool, Private Terrace & Wi-Fi

Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Montespertoli
10.0 out of 10, Exceptional, (1 review)
"The Villa was charming and absolutely bursting with character. We loved exploring the house and the grounds! It was quiet and relaxing, but still only a short drive from Florence, Sienna, San Gimignano and other favorite towns of Tuscany. A memorable stay in an absolutely unique villa!"
United States
Scott M.
The price is SAR 9,460
SAR 9,469 total
includes taxes & fees
1 Sep - 2 Sep
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
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

The Social Hub Florence Lavagnini

The Social Hub Florence Lavagnini

10/10 Excellent
"Great hotel with helpful amenities: gym, laundry, restaurants plus the tram was just outside so it made getting to the airport extremely easy!"
Samantha 4-night trip
Posted 14 hours ago
The Social Hub Florence Lavagnini

Frequently asked questions

How much do villas in Castellina in Chianti cost?
Villas in Castellina in Chianti range between SAR 574 and SAR 25,685 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 1852 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.