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

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Chianti Region villas

Property grounds

1. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Tavarnelle Val di Pesa
The price is €135
includes taxes & fees
8 Sept - 9 Sept
Rooster House, cooking classes and opera
Exterior

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 €457
includes taxes & fees
7 Sept - 8 Sept
Villa Il Signorino
Outdoor dining

3. Villa with Pool - Two Bedrooms

Villa with Pool - Two Bedrooms
Rignano sull'Arno (Florence)
The price is €240
includes taxes & fees
1 Oct - 2 Oct
Villa with Pool - Two Bedrooms
Pool

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 €964
includes taxes & fees
17 Sept - 18 Sept
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Property grounds

5. 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 €844
includes taxes & fees
4 Oct - 5 Oct
Villino Tre Pini | Panoramic Private Pool, Nature & Privacy
Outdoor dining

6. 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 €391
includes taxes & fees
12 Sept - 13 Sept
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Exterior

7. 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 €454
includes taxes & fees
7 Oct - 8 Oct
My Exclusive Italy - Classic Suite in a Luxury Wine Estate
Outdoor dining

8. Villa with Pool - 3 Bedrooms with independent bathroom

Villa with Pool - 3 Bedrooms with independent bathroom
Rignano sull'Arno
The price is €347
includes taxes & fees
15 Sept - 16 Sept
Villa with Pool - 3 Bedrooms with independent bathroom
Terrace/patio

9. The San Leonino House

The San Leonino House
Castellina in Chianti
The price is €1,323
includes taxes & fees
8 Sept - 9 Sept
The San Leonino House
Outdoor dining

10. Villa Bellavista - Homelike Villas

Villa Bellavista - Homelike Villas
Montegonzi
Villa Bellavista - Homelike Villas
Outdoor pool

11. 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

12. 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 €561
includes taxes & fees
7 Oct - 8 Oct
My Exclusive Italy - Exclusive Suite with view in a Luxury Wine Estate
Property grounds

13. "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.
"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
Exterior

14. 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 €825
includes taxes & fees
7 Oct - 8 Oct
My Exclusive Italy - Presidential Suite with view in a Luxury Wine Estate
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 €627
includes taxes & fees
7 Sept - 8 Sept
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
Exterior

16. Exclusive Estate | Personal Concierge & Heated Pool

Exclusive Estate | Personal Concierge & Heated Pool
impruneta
10.0 out of 10, Exceptional, (113 reviews)
"The Villa and grounds are absolutely beautiful! Caterina and her family members were the most gracious hosts. They could not do enough to make sure we had a "once in a lifetime" multi-generational family trip and truly made us feel like part of their family during our stay. We loved every second of our time in Tuscany and would highly recommend this amazing property."
United States
Charles S.
The price is €1,281
includes taxes & fees
13 Sept - 14 Sept
Exclusive Estate | Personal Concierge & Heated Pool
Terrace/patio

17. 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
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 traveller
The price is €1,146
includes taxes & fees
10 Sept - 11 Sept
Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi
Exterior

19. 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 €2,162
includes taxes & fees
8 Sept - 9 Sept
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Property grounds

20. 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.
Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
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

Castello Vicchiomaggio

Castello Vicchiomaggio

10/10 Excellent
"Very nice place in the heart of Chianti Pool and premises are extraordinary"
Maryse 3-night trip
Posted 3 hours ago
Castello Vicchiomaggio

Find out more about Chianti Region

Chianti Region Villas information

Number of reviews
136
Accommodation
529 Villas
Lowest Price
€135
Highest Price
€2,378

Frequently asked questions

How much do villas in Chianti Region cost?
Villas in Chianti Region cost between €135 and €2,378 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 529 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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