Villas in Chianti Region

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Dec 5 - Dec 7
In two months
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In three months
Feb 13 - Feb 15
In four months
Mar 13 - Mar 15

Villas in Chianti Region

Pool
CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28

CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28

Gaiole in Chianti
$7,470 nightly
The price is $7,470
Nov 20 - Nov 21
Total with taxes and fees
CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28
Exterior
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!

Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!

Montespertoli
10.0 out of 10, Exceptional, (12)
"Amazing Property! The house was impeccably clean, with spacious bedrooms and comfortable beds. Our gracious host Nicola spoiled us with his generosity. He went beyond our expectations to ensure that our stay was perfect. He and his wife welcomed us with a delicious homemade apple cake. He drove us to the nearby town of Montespertoli to pick-up groceries and provisions. He recommended a local chef to cook for us at the villa. The meal was amazing and memorable. We will be back!"
United States
Elise D.
$1,649 nightly
The price is $1,654
Nov 20 - Nov 21
Total with taxes and fees
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
Terrace/patio
"Villa Erbolino" with Private Garden, Outdoor Stone Bathtub & Wi-Fi

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

Gaiole in Chianti
10.0 out of 10, Exceptional, (7)
"Country location but easy access to a great local winery/restaurant and the town of Gaiole."
Canada
russ h.
$655 nightly
The price is $660
Nov 20 - Nov 21
Total with taxes and fees
"Villa Erbolino" with Private Garden, Outdoor Stone Bathtub & Wi-Fi
Terrace/patio
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)
"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."
United States
Lidija M.
$463 nightly
The price is $463
Nov 20 - Nov 21
Total with taxes and fees
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Outdoor pool
Beautiful Tuscan home between Florence & Siena

Beautiful Tuscan home between Florence & Siena

Florence
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. "
United States
Debra P.
$2,304 nightly
The price is $2,304
Nov 20 - Nov 21
Total with taxes and fees
Beautiful Tuscan home between Florence & Siena
Pool
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)
"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.
$1,772 nightly
The price is $1,774
Nov 24 - Nov 25
Total with taxes and fees
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Exterior
Villa con Piscina, Sauna, Jacuzzi

Villa con Piscina, Sauna, Jacuzzi

Toscana
6.0 out of 10, (2)
"Beautiful property, highly recommended. "
United States
Magdalena
$686 nightly
The price is $691
Nov 20 - Nov 21
Total with taxes and fees
Villa con Piscina, Sauna, Jacuzzi
Exterior
Villa with concierge service & heated pool at 20 minute from Florence center

Villa with concierge service & heated pool at 20 minute from Florence center

impruneta
10.0 out of 10, Exceptional, (105)
"Our host (Cate), along with her sister and mother, were fantastic. Very responsive, easy to get ahold of and worked very hard to ensure our visit was amazing. Cate was onsite and worked closely with the catering company and made sure all went well.."
Canada
Tom A.
$1,547 nightly
The price is $1,552
Nov 24 - Nov 25
Total with taxes and fees
Villa with concierge service & heated pool at 20 minute from Florence center
Pool
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, (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."
Poland
Anonymous traveler
$2,034 nightly
The price is $2,039
Dec 2 - Dec 3
Total with taxes and fees
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Property grounds
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)
"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.
$2,447 nightly
The price is $2,450
Nov 21 - Nov 22
Total with taxes and fees
Villa 'Il Frassine' with Private Pool, Wi-Fi and Air Conditioning
Exterior
Villa Gabriella Chianti Toscana

Villa Gabriella Chianti Toscana

Città Metropolitana di Firenze
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...
Canada
Gilles C.
$686 nightly
The price is $691
Nov 20 - Nov 21
Total with taxes and fees
Villa Gabriella Chianti Toscana
Pool
Villa 'Virgilio Colline Del Chianti' with Mountain View, Wi-Fi and Air Conditioning

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

Tavarnelle Val di Pesa
$1,489 nightly
The price is $1,489
Nov 21 - Nov 22
Total with taxes and fees
Villa 'Virgilio Colline Del Chianti' with Mountain View, Wi-Fi and Air Conditioning
Pool
Wedding Villa in Chianti - Villa la Veronica

Wedding Villa in Chianti - Villa la Veronica

Greve in chianti
$2,222 nightly
The price is $2,222
Nov 26 - Nov 27
Total with taxes and fees
Wedding Villa in Chianti - Villa la Veronica
Pool
VILLA TERRAZZA SUL CHIANTI

VILLA TERRAZZA SUL CHIANTI

Greve in Chianti
$2,613 nightly
The price is $2,613
Nov 20 - Nov 21
Total with taxes and fees
VILLA TERRAZZA SUL CHIANTI
Exterior
Mulino Cintoia Chianti Toscana pool, sauna and Jacuzzi experience

Mulino Cintoia Chianti Toscana pool, sauna and Jacuzzi experience

Città Metropolitana di Firenze
2.0 out of 10, (2)
"Reader beware: We have been traveling for years with family and friends, renting homes all over the world. this was our worst experience ever. This can only be described as a scam. The "owners" have at least five listings that we found of the same house so that you don't see the negative reviews. When we arrived, they told us there was no hot water but they were trying to fix it. For the first three days of our four day stay we did not have hot water, but instead of apologizing, the owner was...
United States
Kyia M.
$503 nightly
The price is $508
Nov 20 - Nov 21
Total with taxes and fees
Mulino Cintoia Chianti Toscana pool, sauna and Jacuzzi experience
Exterior
Artisti del Cavallo Tourism

Artisti del Cavallo Tourism

Foiano della Chiana
8.4 out of 10, Very Good, (24)
"Good house for one night. "
Germany
Heiner
$78 nightly
The price is $89
Dec 20 - Dec 21
Total with taxes and fees
Artisti del Cavallo Tourism
Exterior
Il Poggio dell'Eremita

Il Poggio dell'Eremita

Sinalunga
10.0 out of 10, Exceptional, (58)
"Amazing property! Could not recommend more."
United States
Annika P.
$157 nightly
The price is $160
Nov 20 - Nov 21
Total with taxes and fees
Il Poggio dell'Eremita
Exterior detail
VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25

VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25

Careggi Rifredi
10.0 out of 10, Exceptional, (1)
"Staff went over and above for us. Food was wonderful service 5 stars"
United States
robert g.
$11,025 nightly
The price is $11,025
Nov 20 - Nov 21
Total with taxes and fees
VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25
Exterior
Country House with heated pool near the center

Country House with heated pool near the center

Careggi Rifredi
9.4 out of 10, Exceptional, (10)
"The property was outstanding and our family had a blast. It was a nice get away from the crowds in the city to enjoy the animals and greenery of the house on the farm. "
United States
Nancy P.
$542 nightly
The price is $555
Nov 20 - Nov 21
Total with taxes and fees
Country House with heated pool near the center
Pool
VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

Siena
$6,929 nightly
The price is $6,929
Nov 20 - Nov 21
Total with taxes and fees
VILLA CHIGI - Seven Bedroom Villa, Sleeps 14
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

Salvadonica - Borgo del Chianti

Salvadonica - Borgo del Chianti

10/10 Excellent
"Wonderful "
Adrienna 6-night trip
Posted 8 days ago
Salvadonica - Borgo del Chianti

Find out more about Chianti Region

Chianti Region Villas information

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 Villas
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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 vacation 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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