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
4 Sep - 6 Sep
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 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 2,961
SAR 5,806 total
includes taxes & fees
23 Aug - 24 Aug
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 SAR 17,847
SAR 17,860 total
includes taxes & fees
14 Sep - 15 Sep
Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills
TV, books

3. Villa Liberty in The Centre - No Ztl

Villa Liberty in The Centre - No Ztl
Siena Historical Center
The price is SAR 2,882
SAR 2,882 total
includes taxes & fees
20 Sep - 21 Sep
Villa Liberty in The Centre - No Ztl
Exterior

4. 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 SAR 3,731
SAR 3,784 total
includes taxes & fees
23 Aug - 24 Aug
Wonderful Villa Pian dei Giullari with Pool – Elegance and Relaxation in the Heart of Florence
Pool

5. 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 2,354
SAR 4,464 total
includes taxes & fees
17 Sep - 18 Sep
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Property grounds

6. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Toscana
The price is SAR 482
SAR 574 total
includes taxes & fees
19 Sep - 20 Sep
Rooster House, cooking classes and opera
Villa, Air conditioning, Courtyard View | Exterior

7. 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 704
SAR 788 total
includes taxes & fees
3 Sep - 4 Sep
Villa Montecastello
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 SAR 4,738
SAR 4,843 total
includes taxes & fees
24 Aug - 25 Aug
"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 SAR 1,382
SAR 1,935 total
includes taxes & fees
4 Sep - 5 Sep
Villa Il Signorino
Property grounds

10. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Siena
The price is SAR 19,033
SAR 21,225 total
includes taxes & fees
19 Sep - 20 Sep
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Property grounds

11. 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 SAR 1,579
SAR 3,900 total
includes taxes & fees
27 Aug - 28 Aug
Villino Tre Pini | Panoramic Private Pool, Nature & Privacy
Exterior

12. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is SAR 7,528
SAR 8,498 total
includes taxes & fees
30 Aug - 31 Aug
Villa Torre Among the Hills of Siena
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 SAR 4,691
SAR 5,660 total
includes taxes & fees
24 Aug - 25 Aug
Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
Outdoor dining

14. Villa Bellavista - Homelike Villas

Villa Bellavista - Homelike Villas
Montegonzi
Villa Bellavista - Homelike Villas
Outdoor dining

15. 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 1,097
SAR 1,645 total
includes taxes & fees
29 Aug - 30 Aug
Luxury Villa in the Florentine hills
Terrace/patio

16. 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 2,069
SAR 2,603 total
includes taxes & fees
23 Aug - 24 Aug
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
Exterior

17. Apartment in villa with pool, A/C, WIFI, TV, terrace, panoramic view, close to San Gimignano

Apartment in villa with pool, A/C, WIFI, 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 632
SAR 721 total
includes taxes & fees
28 Aug - 29 Aug
Apartment in villa with pool, A/C, WIFI, TV, terrace, panoramic view, close to San Gimignano
Exterior

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

Villa "Arnilù" with Private Pool & Wi-Fi
San Gimignano
The price is SAR 21,668
SAR 23,295 total
includes taxes & fees
22 Aug - 23 Aug
Villa "Arnilù" with Private Pool & Wi-Fi
Outdoor dining

19. 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 6,067
SAR 6,085 total
includes taxes & fees
29 Aug - 30 Aug
Villa 'Molino' with Private Pool, Private Terrace and Wi-Fi
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 SAR 1,129
SAR 1,546 total
includes taxes & fees
23 Aug - 24 Aug
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

The Hoxton, Florence

The Hoxton, Florence

10/10 Excellent
"Always great to stay at the Hoxton. Great staff, beautiful property, big and clean rooms."
Tavleen 1-night trip
Posted less than an hour ago
The Hoxton, Florence

Frequently asked questions

How much do villas in Castellina in Chianti cost?
Villas in Castellina in Chianti range between SAR 574 and SAR 23,295 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.