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Check prices for these dates

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17 Oct - 19 Oct
In two weeks
24 Oct - 26 Oct
In one month
7 Nov - 9 Nov
In two months
5 Dec - 7 Dec

Featured Villas in Chianti Region and around

Villa con Piscina, Sauna, Jacuzzi
Exterior

Villa con Piscina, Sauna, Jacuzzi

6.0 out of 10, (2)
"Beautiful property, highly recommended. "
The price is €597
includes taxes & fees
2 Nov - 3 Nov
Villa con Piscina, Sauna, Jacuzzi
Villa Il Signorino
Exterior

Villa Il Signorino

10.0 out of 10, Exceptional, (2)
"Nice place 👌 "
The price is €456
includes taxes & fees
12 Oct - 13 Oct
Villa Il Signorino
"Villa Erbolino" with Private Garden, Outdoor Stone Bathtub & Wi-Fi
Terrace/patio

"Villa Erbolino" with Private Garden, Outdoor Stone Bathtub & Wi-Fi

10.0 out of 10, Exceptional, (7)
"Country location but easy access to a great local winery/restaurant and the town of Gaiole."
The price is €804
includes taxes & fees
6 Nov - 7 Nov
"Villa Erbolino" with Private Garden, Outdoor Stone Bathtub & Wi-Fi
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Terrace/patio

Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~

10.0 out of 10, Exceptional, (3)
"Pictures do not do it justice, this house and location is absolutely beautiful. Very comfortable beds, clean house, beauty views, nice fireplace.owner goes above and beyond to make you feel welcome. She had her local wine, cooked us a delishes breakfast, and also brought her olive oil to do tasting. We will definitely be back, i thank you for an amazing experience and a beautiful house."
The price is €413
includes taxes & fees
20 Oct - 21 Oct
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28
Pool

CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28

The price is €6,450
includes taxes & fees
12 Oct - 13 Oct
CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Pool

Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

10.0 out of 10, Exceptional, (1)
"Pros: Świetna lokalizacja i przyjemne otoczenie domu. Dom położony na wzniesieniu z którego roztaczał się piękny widok. Cons: Osoba opiekująca się domem nie mówiła po angielsku co utrudniało komunikację. Nie byliśmy świadomi że dom podzielony jest na 2 części góra i piwnica w której były dodatkowe 3 pokoje. Uszkodzona pralka która nie dopierała pranych ubrań - brudna woda z zanieczyszczeniami które dodatkowo brudziły ubrania."
The price is €1,761
includes taxes & fees
1 Nov - 2 Nov
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
VILLA SOLATA - Nine Bedroom Villa, Sleeps 20
Pool

VILLA SOLATA - Nine Bedroom Villa, Sleeps 20

VILLA SOLATA - Nine Bedroom Villa, Sleeps 20
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Pool

Villa Milani with Shared Pool, Private Terrace & Wi-Fi

10.0 out of 10, Exceptional, (1)
"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!"
The price is €1,429
includes taxes & fees
13 Oct - 14 Oct
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Villa 'Vanna - Certaldo' with Garden & Wi-Fi
Terrace/patio

Villa 'Vanna - Certaldo' with Garden & Wi-Fi

The price is €583
includes taxes & fees
12 Oct - 13 Oct
Villa 'Vanna - Certaldo' with Garden & Wi-Fi
Beautiful Tuscan home between Florence & Siena
Outdoor pool

Beautiful Tuscan home between Florence & Siena

10.0 out of 10, Exceptional, (6)
"From the moment we entered to our last day everything was perfect. Group of 15 and we all fit comfortably. "
The price is €1,704
includes taxes & fees
12 Oct - 13 Oct
Beautiful Tuscan home between Florence & Siena
Villa 'Il Frassine' with Private Pool, Wi-Fi and Air Conditioning
Property grounds

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

10.0 out of 10, Exceptional, (1)
The price is €2,114
includes taxes & fees
13 Oct - 14 Oct
Villa 'Il Frassine' with Private Pool, Wi-Fi and Air Conditioning
4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC
Outdoor pool

4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC

8.0 out of 10, Very good, (1)
"We spent a great family time at Adme’s house.The house has everything. Was very clean and well maintained . Will highly recommend."
The price is €1,291
includes taxes & fees
15 Oct - 16 Oct
4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC
Villa Gabriella Chianti Toscana
Exterior

Villa Gabriella Chianti Toscana

6.0 out of 10, (1)
"le gestionnaire ne répond que très peu a nos courriels. C’est une superbe résidence qui manque malheureusement d’entretien. Des fourmis a l’entrée aux toiles d’araignées, mais surtout une forte odeur de moisissure qui embaume le 2eme étage au complet et même les draps et les matelas. Dans la cuisine: une forte odeur de créosote est présente dès que l’on ferme la porte. Le four au gas ne fonctionne pas. Le plafond coule. La piscine est superbe mais tous les coussins du mobilier extérieur sont...
The price is €597
includes taxes & fees
2 Nov - 3 Nov
Villa Gabriella Chianti Toscana
Villa Bellavista - Homelike Villas
Pool

Villa Bellavista - Homelike Villas

Villa Bellavista - Homelike Villas
Villa 'Virgilio Colline Del Chianti' with Mountain View, Wi-Fi and Air Conditioning
Pool

Villa 'Virgilio Colline Del Chianti' with Mountain View, Wi-Fi and Air Conditioning

The price is €1,549
includes taxes & fees
6 Nov - 7 Nov
Villa 'Virgilio Colline Del Chianti' with Mountain View, Wi-Fi and Air Conditioning
Wedding Villa in Chianti - Villa la Veronica
Pool

Wedding Villa in Chianti - Villa la Veronica

The price is €1,974
includes taxes & fees
20 Oct - 21 Oct
Wedding Villa in Chianti - Villa la Veronica
Mulino Cintoia Chianti Toscana pool, sauna and Jacuzzi experience
Exterior

Mulino Cintoia Chianti Toscana pool, sauna and Jacuzzi experience

2.0 out of 10, (2)
Mulino Cintoia Chianti Toscana pool, sauna and Jacuzzi experience
Artisti del Cavallo Tourism
Exterior

Artisti del Cavallo Tourism

8.4 out of 10, Very good, (24)
"Ottimo agriturismo silenzioso con persone molto gentilissime "
The price is €85
includes taxes & fees
12 Oct - 13 Oct
Artisti del Cavallo Tourism
Il Poggio dell'Eremita
Exterior

Il Poggio dell'Eremita

10.0 out of 10, Exceptional, (57)
"Located in a peaceful location, the house is charming and homey. The hosts are very kind and accommodating, and we had a wonderful stay. The view from the bedroom balcony is spectacular."
The price is €142
includes taxes & fees
20 Oct - 21 Oct
Il Poggio dell'Eremita
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

Torre a Cona Wine Estate

Torre a Cona Wine Estate

10/10 Excellent
"Beautiful place"
Shariza 3-night trip
Posted 2 days ago
Torre a Cona Wine Estate

Find out more about Chianti Region

Chianti Region Villas information

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Frequently asked questions

How much do villas in Chianti Region cost?
Villas in Chianti Region cost between and 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 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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