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Check prices for these dates

In two weeks
Jun 19 - Jun 21
In two months
Jul 31 - Aug 2
In three months
Aug 28 - Aug 30
In four months
Sep 25 - Sep 27

Our top choices for Chianti Region villas

Outdoor dining

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 ￥49,608
￥80,117 total
includes taxes & fees
Jun 12 - Jun 13
VILLA in FLORENTINE HILLS. 220+ EXCELLENT REVIEWS. 100% travelers recommend.
Exterior

Villa Marcolina

Villa Marcolina
Castelnuovo Berardenga
The price is ￥128,441
￥142,762 total
includes taxes & fees
Jul 7 - Jul 8
Villa Marcolina
Property grounds

Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Toscana
The price is ￥18,284
￥22,162 total
includes taxes & fees
Jun 8 - Jun 9
Rooster House, cooking classes and opera
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 ￥55,258
￥74,096 total
includes taxes & fees
Jun 10 - Jun 11
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
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 ￥83,754
￥92,130 total
includes taxes & fees
Jun 7 - Jun 8
My Exclusive Italy - Classic Suite in a Luxury Wine Estate
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 ￥58,176
￥84,032 total
includes taxes & fees
Jun 7 - Jun 8
Villa Il Signorino
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 ￥102,577
￥112,835 total
includes taxes & fees
Jun 8 - Jun 9
My Exclusive Italy - Exclusive Suite with view in a Luxury Wine Estate
Pool

Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi

Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi
Bucine
10.0 out of 10, Exceptional, (2 reviews)
"Upon arrival Guido had everything prepared for us. A bottle of his amazing wine that he makes along with 2 wine glasses we’re waiting on the farmhouse table. The home had 2 very comfortable bedrooms and a bathroom along with a living room and kitchen. Front porch overlooks the stunning Tuscany fields. The swimming pool was refreshing and everything was beyond perfect. This location was everything and more. The hosts were so helpful. I will come back her again..make sure to take time for the...
United States
Marianne H.
The price is ￥65,010
￥72,951 total
includes taxes & fees
Jun 11 - Jun 12
Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi
Pool

Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed

Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed
Bucine
The price is ￥58,861
￥66,850 total
includes taxes & fees
Jun 10 - Jun 11
Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed
Exterior

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 ￥265,878
￥304,524 total
includes taxes & fees
Jun 14 - Jun 15
Luxury Tuscan Villa with Private Heated Pool, Concierge service & Timeless Views
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 ￥197,468
￥238,284 total
includes taxes & fees
Jun 9 - Jun 10
Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
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 ￥141,160
￥155,276 total
includes taxes & fees
Jun 11 - Jun 12
My Exclusive Italy - Presidential Suite with view in a Luxury Wine Estate
Terrace/patio

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
Exterior

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 ￥369,374
￥474,830 total
includes taxes & fees
Jun 17 - Jun 18
Beautiful Tuscan home between Florence & Siena
Terrace/patio

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 ￥97,299
￥119,823 total
includes taxes & fees
Jun 7 - Jun 8
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
Exterior

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 ￥365,681
￥366,050 total
includes taxes & fees
Jun 8 - Jun 9
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Exterior

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
The price is ￥2,615,170
￥2,615,170 total
includes taxes & fees
Jun 13 - Jun 14
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Pool

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 traveler
The price is ￥177,931
￥212,455 total
includes taxes & fees
Jun 8 - Jun 9
Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi
Exterior

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 ￥255,409
￥301,195 total
includes taxes & fees
Jun 9 - Jun 10
Villa 'Martignana' with Private Pool, Private Garden and Wi-Fi
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, (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 ￥359,032
￥363,464 total
includes taxes & fees
Jun 13 - Jun 14
"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
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

Relais Vignale & Spa

Relais Vignale & Spa

10/10 Excellent
"Wonderful wonderful hotel in a wonderful location. Staff were all very friendly and sweet, particularly with our daughter who they all were wonderful to. Property was stunning and location was just wonderful. Pool area and gardens/grounds were delightful. Would 100% come back and stay again!"
Andrew 4-night trip
Posted 6 hours ago
Relais Vignale & Spa

Find out more about Chianti Region

Chianti Region Villas information

Number of reviews
147
Accommodation
564 Villas
Lowest Price
￥22,162
Highest Price
￥2,615,170

Frequently asked questions

How much do villas in Chianti Region cost?
Villas in Chianti Region cost between ￥22,162 and ￥2,615,170 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 564 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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