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
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Castellina in Chianti villas

Terrace/patio

1. The San Leonino House

The San Leonino House
Castellina in Chianti
The price is SAR 2,930
SAR 5,745 total
includes taxes & fees
7 Sep - 8 Sep
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 18,502
SAR 18,515 total
includes taxes & fees
21 Aug - 22 Aug
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 SAR 4,041
SAR 4,093 total
includes taxes & fees
9 Aug - 10 Aug
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 SAR 476
SAR 567 total
includes taxes & fees
6 Sep - 7 Sep
Rooster House, cooking classes and opera
Villa, Air conditioning, Courtyard View | Exterior

5. Villa Montecastello

Villa Montecastello
Monteriggioni
7.0 out of 10, Good, (2 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 716
SAR 801 total
includes taxes & fees
10 Aug - 11 Aug
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 SAR 4,643
SAR 6,723 total
includes taxes & fees
1 Sep - 2 Sep
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Exterior

7. Villa Marcolina

Villa Marcolina
Castelnuovo Berardenga
The price is SAR 3,186
SAR 3,539 total
includes taxes & fees
9 Aug - 10 Aug
Villa Marcolina
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 6,775
SAR 6,878 total
includes taxes & fees
13 Aug - 14 Aug
"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
Property grounds

9. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Siena
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Exterior

10. 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 1,514
SAR 2,111 total
includes taxes & fees
1 Sep - 2 Sep
Villa Il Signorino
Exterior

11. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is SAR 7,208
SAR 8,167 total
includes taxes & fees
12 Aug - 13 Aug
Villa Torre Among the Hills of Siena
Outdoor dining

12. Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
The price is SAR 6,704
SAR 7,663 total
includes taxes & fees
10 Aug - 11 Aug
Villa Capanna: A Window onto Tuscany
Property grounds

13. 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)
Villino Tre Pini | Panoramic Private Pool, Nature & Privacy
Pool

14. "Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi

"Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi
Certaldo
"Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi
Exterior

15. Portion of Villa Il Conventino with Pool and Wi-Fi

Portion of Villa Il Conventino with Pool and Wi-Fi
San Casciano in Val di Pesa
The price is SAR 11,396
SAR 15,459 total
includes taxes & fees
13 Aug - 14 Aug
Portion of Villa Il Conventino with Pool and Wi-Fi
Exterior

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

Nice apartment in villa with A/C, WIFI, pool, 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 SAR 625
SAR 713 total
includes taxes & fees
21 Aug - 22 Aug
Nice apartment in villa with A/C, WIFI, pool, TV, terrace and panoramic view, close to San Gimig...
Exterior

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

Villa "Arnilù" with Private Pool & Wi-Fi
San Gimignano
The price is SAR 23,821
SAR 25,430 total
includes taxes & fees
7 Sep - 8 Sep
Villa "Arnilù" with Private Pool & Wi-Fi
Outdoor dining

18. Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (149 reviews)
"Lovely property, nicely appointed, would be happy to stay there again."
United States
David K.
The price is SAR 1,082
SAR 1,687 total
includes taxes & fees
29 Aug - 30 Aug
Luxury Villa in the Florentine hills
Terrace/patio

19. 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 2,049
SAR 2,578 total
includes taxes & fees
9 Aug - 10 Aug
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
Outdoor dining

20. 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 6,003
SAR 6,020 total
includes taxes & fees
23 Aug - 24 Aug
Villa 'Molino' with Private Pool, Private Terrace and 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

Palazzo Montebello

Palazzo Montebello

8/10 Good
"I traveled with my husband and daughter and stayed 4 nights from 7/25-7/29. I had requested earlier check-in by contacting the hotel directly through Expedia as long hours in the flight and then, train. The hotel staff indicated they didn’t receive my message. They made us wait for 2.5 hours. The lady who was at the reception desk wasn’t really friendly. She also forgot about us after told us to wait. I went to ask her about our room at 2:45pm, she started asking for my name again. I also didn’t appreciate her talking with her colleague in Italian while attending me. The hotel was beautiful. Our room was nice though waste of space with a long closet. The air conditioning wasn’t working properly as room would not get cool enough. When asked for a fan, they didn’t provide one as not available. They told me that we can change the room but that would cause major inconvenience. The room doesn’t have an iron. It is provided based on the availability. The front desk staff on the subsequent days were friendly and helpful. The hotel is about 15 mins walk from the train station and 25-30 mins from Duomo."
Vaidehi 4-night trip
Posted 10 hours ago
Palazzo Montebello

Frequently asked questions

How much do villas in Castellina in Chianti cost?
Villas in Castellina in Chianti range between SAR 567 and SAR 25,430 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 1851 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.