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Browse Select Chianti Region Villas

Relais Badia a Passignano
Aerial view

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
Surrounded by lush greenery, this traditional building offers a serene natural setting with multiple levels and windows.

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

10.0 out of 10, Exceptional, (1)
"This was a lovely rental in Chianti! The space was clean and had everything we needed for an enjoyable and comfortable stay! The hosts are so friendly and the property had such amazing sculpture and art. "
La Casa Nel Bosco D’arte - Passo del Sugame, Greve in Chianti
I Glicini
Relax by the pool surrounded by lush greenery and rolling hills.

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)
"Lovely villa, clean , good amenities, good value for money The only thing I did not like was the location is a little too remote from the nearest town San Polo You had to drive down the hills on a very steep and winedy road as it is a 3 km walk to the shops and bar If you like to be secluded with peace and quiet, this is the place for you."
Villa Panzalla
Borgo La Casina
Traditional stone building with a rustic facade, featuring multiple windows with shutters and a small porch area, set amidst manicured lawns and lush greenery.

Borgo La Casina

Borgo La Casina
Ville Il Paradiso Villa Bellaflore
Relax by the pool in a serene villa setting surrounded by lush green hills.

Ville Il Paradiso Villa Bellaflore

Ville Il Paradiso Villa Bellaflore
Oliveta a Retreat Surrounded by Olive Trees
Relax by the serene pool surrounded by a comfortable deck and shaded areas.

Oliveta a Retreat Surrounded by Olive Trees

Oliveta a Retreat Surrounded by Olive Trees
Villa Chianti in Marcialla
Enjoy a meal al fresco on the patio, surrounded by lush greenery and a charming view.

Villa Chianti in Marcialla

Villa Chianti in Marcialla
La Badia 2
Relax in a serene outdoor space surrounded by lush greenery and trees, featuring a patio, table, and chairs.

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
Escape to a serene vineyard retreat, 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 in a charming outdoor space with a brick archway leading to a lush garden, featuring a sofa and coffee table.

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
Situated in a lush valley, this traditional building features a central courtyard with a swimming pool and a stone bridge crossing a small water channel.

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
Seasonal outdoor pool, pool loungers

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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Top Chianti Region Hotel Reviews

Relais Vignale & Spa

Relais Vignale & Spa

10/10 Excellent
"My friend and I had such a relaxing time at Relais!! We both got amazing massages from Natalie, the staff helped me figure out how to get to Rome after, the rooms were GORGEOUS, the pool was spectacular and got great poolside drinks, and the food/wine was the best!!! Stay here for a romantic and relaxing getaway surrounded by Tuscany’s beautiful rolling hills and vineyards. Would definitely come back!"
mary 1-night trip
Posted 5 days ago
Relais Vignale & Spa

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 53 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.