A vineyard with rows of grapevines, a house surrounded by trees, and a road with vehicles.

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Our top choices for Chianti Region villas

1. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Toscana
The price is HK$1,007
HK$1,199 total
includes taxes & fees
25 Aug - 26 Aug
Rooster House, cooking classes and opera

2. 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 HK$2,884
HK$4,157 total
includes taxes & fees
1 Sept - 2 Sept
Villa Il Signorino

3. 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 HK$2,356
HK$3,216 total
includes taxes & fees
25 Aug - 26 Aug
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~

4. 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 HK$4,913
HK$9,316 total
includes taxes & fees
17 Sept - 18 Sept
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

5. My Exclusive Italy - Classic Suite in a Luxury Wine Estate

My Exclusive Italy - Classic Suite in a Luxury Wine Estate
Rignano sull'Arno
The price is HK$3,592
HK$3,952 total
includes taxes & fees
14 Sept - 15 Sept
My Exclusive Italy - Classic Suite in a Luxury Wine Estate

6. My Exclusive Italy - Exclusive Suite with view in a Luxury Wine Estate

My Exclusive Italy - Exclusive Suite with view in a Luxury Wine Estate
Rignano sull'Arno
The price is HK$4,432
HK$4,875 total
includes taxes & fees
14 Sept - 15 Sept
My Exclusive Italy - Exclusive Suite with view in a Luxury Wine Estate

7. Villa with Pool - Two Bedrooms

Villa with Pool - Two Bedrooms
Rignano sull'Arno (Florence)
The price is HK$1,923
HK$2,298 total
includes taxes & fees
20 Sept - 21 Sept
Villa with Pool - Two Bedrooms

8. Villa Bellavista - Homelike Villas

Villa Bellavista - Homelike Villas
Montegonzi
Villa Bellavista - Homelike Villas

9. "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 HK$9,888
HK$10,108 total
includes taxes & fees
26 Aug - 27 Aug
"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi

10. Villa with Pool - 3 Bedrooms with independent bathroom

Villa with Pool - 3 Bedrooms with independent bathroom
Rignano sull'Arno
The price is HK$3,365
HK$3,793 total
includes taxes & fees
20 Sept - 21 Sept
Villa with Pool - 3 Bedrooms with independent bathroom

11. 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 HK$4,321
HK$5,438 total
includes taxes & fees
25 Aug - 26 Aug
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany

12. The San Leonino House

The San Leonino House
Castellina in Chianti
The price is HK$6,180
HK$12,117 total
includes taxes & fees
25 Aug - 26 Aug
The San Leonino House

13. My Exclusive Italy - Presidential Suite with view in a Luxury Wine Estate

My Exclusive Italy - Presidential Suite with view in a Luxury Wine Estate
Rignano sull'Arno
The price is HK$6,522
HK$7,174 total
includes taxes & fees
18 Sept - 19 Sept
My Exclusive Italy - Presidential Suite with view in a Luxury Wine Estate

14. 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 HK$9,789
HK$11,813 total
includes taxes & fees
25 Aug - 26 Aug
Villa Capannina with Private Pool, Wi-Fi and Air Conditioning

15. 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 HK$19,776
HK$19,795 total
includes taxes & fees
1 Sept - 2 Sept
Villa Milani with Shared Pool, Private Terrace & Wi-Fi

16. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
The price is HK$119,273
HK$119,273 total
includes taxes & fees
25 Aug - 26 Aug
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

17. 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 traveller
The price is HK$8,783
HK$10,494 total
includes taxes & fees
30 Aug - 31 Aug
Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi

18. Villa 'Il Frassine' with Private Pool, Wi-Fi and Air Conditioning

Villa 'Il Frassine' with Private Pool, Wi-Fi and Air Conditioning
Rignano sull'Arno
7.0 out of 10, Good, (2 reviews)
"We arrived after dark, tired from long overnight flight. We had no water pressure upstairs and no hot water anywhere. This was corrected the next day. One on-suite toilette would not flush properly and leaked at the grinder motor. A "tech" was called in. He informed us that he could not fix it, they would need to call someone else. When we continued to report the issue to the host, she informed us that the "tech" said it was working OK. The "tech" informed us that it was not but he could not fix...
United States
Norman C.
The price is HK$23,671
HK$28,733 total
includes taxes & fees
1 Sept - 2 Sept
Villa 'Il Frassine' with Private Pool, Wi-Fi and Air Conditioning

19. Apartments Florence - Villa Fonte Morgana with pool

Apartments Florence - Villa Fonte Morgana with pool
Impruneta
10.0 out of 10, Exceptional, (1 review)
"What a beautiful villa! We thoroughly enjoyed our stay in Tuscan countryside. All rooms were comfortable and large. We were surprised by the lack of body soap and shampoo."
United States
Christine B.
Apartments Florence - Villa Fonte Morgana with pool

20. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is HK$14,140
HK$16,163 total
includes taxes & fees
30 Aug - 31 Aug
Villa Torre Among the Hills of Siena
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 Chianti Region Hotel Reviews

Find out more about Chianti Region

Chianti Region Villas information

Number of reviews
24
Accommodation
547 Villas
Lowest Price
HK$1,199
Highest Price
HK$119,273

Frequently asked questions

How much do villas in Chianti Region cost?
Villas in Chianti Region cost between HK$1,199 and HK$119,273 per night. These escapes 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 Chianti Region?
Chianti Region has 547 villas to choose from. Enter your destination and dates and lock in your perfect trip today.
Why book your villa in Chianti Region with Expedia?
We think arranging a holiday should be a breeze, so if you're looking for villas at a great price, Expedia delivers. Keep costs down and choose an all-inclusive stay, or splurge on a plush villa to spoil the ones you love most. Our handy filters make it easy to find a property in Chianti Region that matches your needs.
How can I find cheap villas in Chianti Region?
With Expedia's user-friendly filter tool, scoring cheap villas in Chianti Region has never been easier. To find stays that won't break the bank, fine-tune your search by star rating, budget and amenities.
What is there to do near my villa in Chianti Region?
Whether you love food, shopping, history or sightseeing, Chianti Region offers something for everyone! The major city of San Gimignano boasts lots of things to do, including Archaeological Museum - Spezieria Santa Fina - Raffaele De Grada Modern and Contemporary Art Gallery, Historical Torture Museum and Ornithological Museum. If you're headed to Radda in Chianti, Castello di Albola, Castello di Radda Winery and Borgo di Vescine - Tenute di Castelvecchi shouldn't be missed.

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