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Check prices for these dates

In two weeks
Apr 17 - Apr 19
In two months
May 29 - May 31
In three months
Jun 26 - Jun 28
In four months
Jul 24 - Jul 26

Our top choices for Chianti Region villas

Exterior

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 ￥64,558
￥71,014 total
includes taxes & fees
Apr 1 - Apr 2
My Exclusive Italy - Classic Suite in a Luxury Wine Estate
Property grounds

"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, (8 reviews)
"Everything about this house is exquisite and very homey. Decors are really tasteful. Outdoors spaces and the views are absolutely beautiful. Kitchen is really well appointed. There is no shortage of dish-wear, silverware and glasses. Location is very central to explore Tuscany. Our host, Lapo is very welcoming and helpful with all recommendations. He is the kind of host that you want to stay in touch and come back to see him. "
United States
Ravin N.
The price is ￥183,100
￥187,494 total
includes taxes & fees
Apr 26 - Apr 27
"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
Pool

CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28

CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28
Gaiole in Chianti
CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28
Exterior

Villa Marcolina

Villa Marcolina
Castelnuovo Berardenga
The price is ￥166,455
￥183,100 total
includes taxes & fees
Apr 6 - Apr 7
Villa Marcolina
Exterior

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 ￥77,287
￥85,016 total
includes taxes & fees
Apr 6 - Apr 7
My Exclusive Italy - Exclusive Suite with view in a Luxury Wine Estate
Exterior

VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
Colle Val D'Elsa
The price is ￥2,160,584
￥2,160,584 total
includes taxes & fees
Apr 2 - Apr 3
VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
Pool

VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18

VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18
Castellina in Chianti
The price is ￥853,431
￥944,981 total
includes taxes & fees
Apr 1 - Apr 2
VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18
Exterior

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
The price is ￥2,592,701
￥2,592,701 total
includes taxes & fees
Apr 23 - Apr 24
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Exterior

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 ￥108,930
￥119,823 total
includes taxes & fees
Apr 2 - Apr 3
My Exclusive Italy - Presidential Suite with view in a Luxury Wine Estate
Exterior

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

Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
Vico dʼArbia
The price is ￥170,393
￥188,520 total
includes taxes & fees
Apr 1 - Apr 2
Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
Outdoor dining

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 ￥54,784
￥72,728 total
includes taxes & fees
Apr 1 - Apr 2
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Terrace/patio

Viniard Villa - Residence Le Rose in Chianti

Viniard Villa - Residence Le Rose in Chianti
Castellina in Chianti
The price is ￥73,240
￥134,762 total
includes taxes & fees
Apr 5 - Apr 6
Viniard Villa - Residence Le Rose in Chianti
Exterior

Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is ￥245,867
￥263,994 total
includes taxes & fees
Apr 4 - Apr 5
Villa Torre Among the Hills of Siena
Exterior

Villa Il Signorino

Villa Il Signorino
GREVE IN CHIANTI
10.0 out of 10, Exceptional, (2 reviews)
"Nice place 👌 "
United States
Avi A.
The price is ￥55,349
￥78,596 total
includes taxes & fees
Apr 24 - Apr 25
Villa Il Signorino
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 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 ￥329,581
￥329,947 total
includes taxes & fees
Apr 2 - Apr 3
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Outdoor dining

Villa Bellavista - Homelike Villas

Villa Bellavista - Homelike Villas
Montegonzi
Villa Bellavista - Homelike Villas
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 reviews)
"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.
The price is ￥291,130
￥333,243 total
includes taxes & fees
Apr 8 - Apr 9
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
Exterior

Beautiful Tuscan home between Florence & Siena

Beautiful Tuscan home between Florence & Siena
Florence
10.0 out of 10, Exceptional, (7 reviews)
"From the moment we entered to our last day everything was perfect. Group of 15 and we all fit comfortably. "
United States
Debra P.
The price is ￥332,096
￥463,458 total
includes taxes & fees
Apr 5 - Apr 6
Beautiful Tuscan home between Florence & Siena
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 review)
"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
The price is ￥205,431
￥322,374 total
includes taxes & fees
Apr 4 - Apr 5
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Exterior

Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites

Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites
Montespertoli
10.0 out of 10, Exceptional, (38 reviews)
"Excellent in every way. Highly recommend"
United States
Ed M.
The price is ￥291,130
￥333,243 total
includes taxes & fees
Apr 8 - Apr 9
Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites
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

Borgo Del Cabreo

Borgo Del Cabreo

10/10 Excellent
"Staff was fantastic, grounds were well groomed, rooms looked recently refurbished and breakfast was wonderful. "
eric 3-night trip
Posted 7 days ago
Borgo Del Cabreo

Find out more about Chianti Region

Chianti Region Villas information

Number of reviews
71
Accommodation
540 Villas
Lowest Price
￥72,728
Highest Price
￥2,592,701

Frequently asked questions

How much do villas in Chianti Region cost?
Villas in Chianti Region cost between ￥72,728 and ￥2,592,701 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 540 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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