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Our top choices for Chianti Region villas

Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Toscana
The price is €124
includes taxes & fees
2 Jun - 3 Jun
Rooster House, cooking classes and opera

VILLA in FLORENTINE HILLS. 220+ EXCELLENT REVIEWS. 100% travelers recommend.

VILLA in FLORENTINE HILLS. 220+ EXCELLENT REVIEWS. 100% travelers recommend.
Florence
10.0 out of 10, Exceptional, (9 reviews)
"We had a lovely stay at this place in the country! It was charming, Paola and family were wonderful and we would stay here again!"
United States
Becky F.
The price is €500
includes taxes & fees
12 Jun - 13 Jun
VILLA in FLORENTINE HILLS. 220+ EXCELLENT REVIEWS. 100% travelers recommend.

Villa Marcolina

Villa Marcolina
Castelnuovo Berardenga
The price is €818
includes taxes & fees
2 Jun - 3 Jun
Villa Marcolina

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 €451
includes taxes & fees
2 Jun - 3 Jun
Villa Il Signorino

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 €499
includes taxes & fees
7 Jun - 8 Jun
My Exclusive Italy - Classic Suite in a Luxury Wine Estate

AGRITURISMO in FLORENTINE HILLS-CHIANTI. 100% Travelers Recommend.

AGRITURISMO in FLORENTINE HILLS-CHIANTI. 100% Travelers Recommend.
Pontassieve, Florence
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful, quiet and peaceful."
United States
Tim G.
AGRITURISMO in FLORENTINE HILLS-CHIANTI. 100% Travelers Recommend.

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 €611
includes taxes & fees
29 Jun - 30 Jun
My Exclusive Italy - Exclusive Suite with view in a Luxury Wine Estate

Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is €1,765
includes taxes & fees
2 Jun - 3 Jun
Villa Torre Among the Hills of Siena

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 €1,290
includes taxes & fees
1 Jun - 2 Jun
Villa Capannina with Private Pool, Wi-Fi and Air Conditioning

Luxury Tuscan Villa with Private Heated Pool, Concierge service & Timeless Views

Luxury Tuscan Villa with Private Heated Pool, Concierge service & Timeless Views
impruneta
10.0 out of 10, Exceptional, (109 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 €1,178
includes taxes & fees
1 Jun - 2 Jun
Luxury Tuscan Villa with Private Heated Pool, Concierge service & Timeless Views

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 €1,150
includes taxes & fees
3 Jun - 4 Jun
Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi

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 €841
includes taxes & fees
29 Jun - 30 Jun
My Exclusive Italy - Presidential Suite with view in a Luxury Wine Estate

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 €649
includes taxes & fees
1 Jun - 2 Jun
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany

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 €1,982
includes taxes & fees
2 Jun - 3 Jun
Villa Milani with Shared Pool, Private Terrace & Wi-Fi

Villa 'Martignana' with Private Pool, Private Garden and Wi-Fi

Villa 'Martignana' with Private Pool, Private Garden and Wi-Fi
Empoli
10.0 out of 10, Exceptional, (1 review)
"The villa is divided into 4 apartments and was perfect for our group of eleven. The property was beautiful and it is convenient to the Empoli train station."
United States
Vicki C.
The price is €1,631
includes taxes & fees
2 Jun - 3 Jun
Villa 'Martignana' with Private Pool, Private Garden and Wi-Fi

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
The price is €14,160
includes taxes & fees
1 Jun - 2 Jun
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

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 traveller
The price is €1,907
includes taxes & fees
2 Jun - 3 Jun
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

Beautiful Tuscan home between Florence & Siena

Beautiful Tuscan home between Florence & Siena
Florence
10.0 out of 10, Exceptional, (8 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 €2,508
includes taxes & fees
5 Jun - 6 Jun
Beautiful Tuscan home between Florence & Siena

"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)
"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 €1,464
includes taxes & fees
13 Jun - 14 Jun
"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi

VILLA CHIANTI CLASSICO

VILLA CHIANTI CLASSICO
Greve in Chianti
10.0 out of 10, Exceptional, (1 review)
"It was better than the pictures! The pool was amazing! It was an absolute trip to remember! The winery right down the street also a bonus!!"
United States
Anonymous traveller
The price is €5,664
includes taxes & fees
4 Jun - 5 Jun
VILLA CHIANTI CLASSICO
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
156
Accommodation
534 Villas
Lowest Price
€124
Highest Price
€14,160

Frequently asked questions

How much do villas in Chianti Region cost?
Villas in Chianti Region cost between €124 and €14,160 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 534 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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