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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Castellina in Chianti villas

Villa, Air conditioning, Courtyard View | Exterior

1. 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 AED 627
AED 702 total
includes taxes & fees
25 Sep - 26 Sep
Villa Montecastello
Property grounds

2. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Tavarnelle Val di Pesa
The price is AED 462
AED 517 total
includes taxes & fees
25 Sep - 26 Sep
Rooster House, cooking classes and opera
Pool

3. 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 AED 5,538
AED 7,559 total
includes taxes & fees
4 Oct - 5 Oct
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Property grounds

4. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32
Siena
The price is AED 27,386
AED 29,488 total
includes taxes & fees
23 Oct - 24 Oct
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32
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 AED 6,054
AED 6,155 total
includes taxes & fees
6 Oct - 7 Oct
"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 AED 1,324
AED 1,892 total
includes taxes & fees
24 Sep - 25 Sep
Villa Il Signorino
Pool

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

"Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi
Certaldo
The price is AED 21,190
AED 23,221 total
includes taxes & fees
12 Oct - 13 Oct
"Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi
Exterior

8. Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests

Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
Montespertoli
The price is AED 25,227
AED 25,243 total
includes taxes & fees
14 Oct - 15 Oct
Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
Outdoor dining

9. Villa Bellavista - Homelike Villas

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

10. Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
Villa Capanna: A Window onto Tuscany
Exterior

11. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is AED 6,273
AED 7,202 total
includes taxes & fees
17 Oct - 18 Oct
Villa Torre Among the Hills of Siena
Outdoor dining

12. Molino In Chianti - Villa with Private Pool

Molino In Chianti - Villa with Private Pool
Mercatale Val Di Pesa
The price is AED 5,814
AED 5,831 total
includes taxes & fees
25 Sep - 26 Sep
Molino In Chianti - Villa with Private Pool
Exterior

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

Villa "Arnilù" with Private Pool & Wi-Fi
San Gimignano
The price is AED 20,766
AED 22,325 total
includes taxes & fees
28 Sep - 29 Sep
Villa "Arnilù" with Private Pool & Wi-Fi
Outdoor dining

14. Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (150 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 AED 841
AED 1,396 total
includes taxes & fees
12 Oct - 13 Oct
Luxury Villa in the Florentine hills
Outdoor dining

15. 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 AED 8,409
AED 11,024 total
includes taxes & fees
22 Oct - 23 Oct
Villa Mami: A Tuscan Retreat of Elegance and Charm
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 AED 1,938
AED 2,451 total
includes taxes & fees
1 Oct - 2 Oct
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
Exterior

17. GuestHost - Porta Romana Elegant House with Private Parking!

GuestHost - Porta Romana Elegant House with Private Parking!
Siena
9.0 out of 10, Wonderful, (4 reviews)
"Excellent location 15 mi minute walk to the center of town. Towels and linens were fresh and fragrant. On site parking was super convenient because of limited parking around the town. The property manager was immediately available by phone and delivered an extra blanket which in 5 minutes of our request."
United States
Kathleen M.
The price is AED 804
AED 1,481 total
includes taxes & fees
5 Oct - 6 Oct
GuestHost - Porta Romana Elegant House with Private Parking!
Outdoor dining

18. 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 AED 3,887
AED 4,673 total
includes taxes & fees
12 Oct - 13 Oct
Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi
Outdoor dining

19. 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 AED 1,186
AED 1,586 total
includes taxes & fees
24 Sep - 25 Sep
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Outdoor pool

20. 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
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 Albani Firenze

Hotel Albani Firenze

10/10 Excellent
"Room was Clean, Staff well trained. Breakfast okay. Air conditioning was very good in the rooms. A super busy hotel."
Ken 2-night trip
Posted 6 hours ago
Hotel Albani Firenze

Frequently asked questions

How much do villas in Castellina in Chianti cost?
Villas in Castellina in Chianti range between AED 517 and AED 29,488 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.