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Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sept - 14 Sept

Featured Villas in Chianti Region

Relais Badia a Passignano
Seasonal outdoor pool

Relais Badia a Passignano

10.0 out of 10, Exceptional, (1)
Relais Badia a Passignano
La Casa Nel Bosco D’arte - Passo del Sugame, Greve in Chianti
Experience a serene outdoor setting with a rustic stone building, intricate wire sculpture, and lush greenery, perfect for relaxation.

La Casa Nel Bosco D’arte - Passo del Sugame, Greve in Chianti

La Casa Nel Bosco D’arte - Passo del Sugame, Greve in Chianti
I Glicini
Relax by the serene pool surrounded by lush greenery and vineyards.

I Glicini

I Glicini
Villa Sabrina
Relax by the clear pool surrounded by lush greenery and comfortable seating.

Villa Sabrina

Villa Sabrina
Villa Panzalla
Surrounded by lush greenery and terraced fields, this charming village offers a serene escape.

Villa Panzalla

9.0 out of 10, Wonderful, (2)
Villa Panzalla
Borgo La Casina
Enjoy al fresco dining in a serene setting surrounded by lush greenery and a stone fireplace.

Borgo La Casina

Borgo La Casina
Ville Il Paradiso Villa Bellaflore
Cozy retreat with a fireplace, chandelier, and seating area.

Ville Il Paradiso Villa Bellaflore

Ville Il Paradiso Villa Bellaflore
Oliveta a Retreat Surrounded by Olive Trees
Relax by the serene pool surrounded by lush greenery and tall cypress trees.

Oliveta a Retreat Surrounded by Olive Trees

Oliveta a Retreat Surrounded by Olive Trees
Villa Chianti in Marcialla
Relax in a serene outdoor space with a hot tub, lounge area, and beautifully manicured lawn.

Villa Chianti in Marcialla

Villa Chianti in Marcialla
La Badia 2
Relax by the serene pool surrounded by lush greenery and a quaint building in the background.

La Badia 2

10.0 out of 10, Exceptional, (1)
"Our flight was diverted to another airport, so we were 6 hours later than expected, but able to communicate and get a quick response throughout. It's quite a small place, but there are only two of us, and we had everything we needed. The road in could be quite bumpy or extremely bumpy depending on which way, but we were able to do it in our economy car. The property host was there to meet us in the dark in a downpour, and made us feel welcome- even with a strong language barrier. Pros: view...
La Badia 2
Borgo San Polino a Charming Eco-lodge
Relax by the serene pool surrounded by lush greenery and comfortable seating options.

Borgo San Polino a Charming Eco-lodge

Borgo San Polino a Charming Eco-lodge
Casale Al Sole Tra Le Vecchie Vigne 6
Stroll along the winding path, flanked by traditional street lamps, to a serene bench amidst rolling hills and lush greenery.

Casale Al Sole Tra Le Vecchie Vigne 6

Casale Al Sole Tra Le Vecchie Vigne 6
Spacious Apartment in Villa With Pool
Relax by the pool surrounded by lush greenery and rolling hills.

Spacious Apartment in Villa With Pool

10.0 out of 10, Exceptional, (1)
"Fantastic location. Friendly owners. Very nice property."
Spacious Apartment in Villa With Pool
Villa Casa al Sole Large Private Pool Wifi - 3078
Relax by the serene pool surrounded by lush greenery and traditional architecture.

Villa Casa al Sole Large Private Pool Wifi - 3078

Villa Casa al Sole Large Private Pool Wifi - 3078
Mulino Cintoia Chianti Toscana Pool, Sauna and Jacuzzi Experience
Relax by the pool in a serene outdoor setting with a covered seating area and comfortable dining space.

Mulino Cintoia Chianti Toscana Pool, Sauna and Jacuzzi Experience

Mulino Cintoia Chianti Toscana Pool, Sauna and Jacuzzi Experience
Tenuta di Bibbiano - I Sodi
Enjoy dining al fresco under a charming stone structure with a large table and comfortable seating for six.

Tenuta di Bibbiano - I Sodi

Tenuta di Bibbiano - I Sodi
Il Prato Vignamaggio Private Pool Nature
Surrounded by a lush garden, this charming building offers a serene countryside setting.

Il Prato Vignamaggio Private Pool Nature

Il Prato Vignamaggio Private Pool Nature
Villa Margherita
Exterior

Villa Margherita

Villa Margherita
Il Casolese Vignamaggio Private Pool
Escape to a serene countryside retreat surrounded by lush greenery and olive groves, featuring a pool and peaceful villa.

Il Casolese Vignamaggio Private Pool

Il Casolese Vignamaggio Private Pool
Ville Il Paradiso - Villa Mia
Relax by the serene pool surrounded by lounge chairs and a shaded area.

Ville Il Paradiso - Villa Mia

Ville Il Paradiso - Villa Mia
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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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 45 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.