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
25 Sep - 27 Sep
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

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 2,944
SAR 5,772 total
includes taxes & fees
9 Sep - 10 Sep
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 2,106
SAR 4,203 total
includes taxes & fees
17 Sep - 18 Sep
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Villa, Air conditioning, Courtyard View | Exterior

3. 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 631
SAR 707 total
includes taxes & fees
19 Sep - 20 Sep
Villa Montecastello
Property grounds

4. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Tavarnelle Val di Pesa
The price is SAR 480
SAR 571 total
includes taxes & fees
9 Sep - 10 Sep
Rooster House, cooking classes and opera
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 10,268
SAR 10,373 total
includes taxes & fees
10 Sep - 11 Sep
"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
Property grounds

6. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Siena
The price is SAR 18,939
SAR 21,119 total
includes taxes & fees
9 Sep - 10 Sep
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Exterior

7. 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 1,374
SAR 1,958 total
includes taxes & fees
9 Sep - 10 Sep
Villa Il Signorino
Property grounds

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

Villino Tre Pini | Panoramic Private Pool, Nature & Privacy
Tavarnelle Val di Pesa
10.0 out of 10, Exceptional, (1 review)
The price is SAR 1,304
SAR 3,659 total
includes taxes & fees
4 Oct - 5 Oct
Villino Tre Pini | Panoramic Private Pool, Nature & Privacy
Outdoor dining

9. Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
The price is SAR 6,736
SAR 7,699 total
includes taxes & fees
14 Sep - 15 Sep
Villa Capanna: A Window onto Tuscany
Exterior

10. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is SAR 6,736
SAR 7,699 total
includes taxes & fees
13 Sep - 14 Sep
Villa Torre Among the Hills of Siena
Exterior detail

11. The three owls of san gimignano

The three owls of san gimignano
San Gimignano
The price is SAR 389
SAR 476 total
includes taxes & fees
18 Sep - 19 Sep
The three owls of san gimignano
Outdoor dining

12. Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (149 reviews)
"The villa is a nicely restored rustic home with a beautiful landscape. I would definitely stay there again!"
United States
melissa r.
The price is SAR 1,090
SAR 1,688 total
includes taxes & fees
20 Sep - 21 Sep
Luxury Villa in the Florentine hills
Outdoor dining

13. Villa Bellavista - Homelike Villas

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

14. 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 6,031
SAR 6,049 total
includes taxes & fees
13 Sep - 14 Sep
Villa 'Molino' with Private Pool, Private Terrace and Wi-Fi
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 2,202
SAR 2,734 total
includes taxes & fees
9 Sep - 10 Sep
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
Exterior

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

Villa "Arnilù" with Private Pool & Wi-Fi
San Gimignano
The price is SAR 23,934
SAR 25,552 total
includes taxes & fees
8 Oct - 9 Oct
Villa "Arnilù" with Private Pool & Wi-Fi
Outdoor pool

17. 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
Exterior

18. 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 15,826
SAR 15,839 total
includes taxes & fees
1 Oct - 2 Oct
Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills
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 4,184
SAR 4,999 total
includes taxes & fees
10 Sep - 11 Sep
Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool 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 1,231
SAR 1,641 total
includes taxes & fees
12 Sep - 13 Sep
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

Grand Hotel Baglioni

Grand Hotel Baglioni

8/10 Good
"All was good"
Gary Edward 4-night trip
Posted 3 hours ago
Grand Hotel Baglioni

Frequently asked questions

How much do villas in Castellina in Chianti cost?
Villas in Castellina in Chianti range between SAR 476 and SAR 25,552 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.