A vineyard with rows of grapevines, a house surrounded by trees, and a road with vehicles.

Chianti Region Vacation Rentals

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Chianti Region vacation rentals

View from room

Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (115 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
The price is ₩137,807
₩154,906 total
includes taxes & fees
Aug 2 - Aug 3
Chianti Village Morrocco
Garden view

Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (43 reviews)
"Good location between to San Gimignano and Florence, lose to the highway."
United States
ALEXANDER
The price is ₩148,215
₩172,990 total
includes taxes & fees
Jul 30 - Jul 31
Villa San Filippo
Terrace/patio

Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (100 reviews)
"A nice blend of old world charm and modern conveniences. It is far from "
United States
John
The price is ₩143,991
₩161,708 total
includes taxes & fees
Jul 31 - Aug 1
Palazzo Pacini
Lounge

Mariani Bed & Breakfast

Mariani Bed & Breakfast
Castellina in Chianti
9.8 out of 10, Exceptional, (17 reviews)
"Very nice and quiet neighbourhood. Close to city centre. The host is very kind."
Japan
Chie
The price is ₩131,807
₩151,624 total
includes taxes & fees
Jul 28 - Jul 29
Mariani Bed & Breakfast
Exterior

L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (14 reviews)
"Monica is a very gracious host. We very much enjoyed our stay. The village is also very quaint and within walking distance. We appreciate the hospitality and highly recommend staying here if you’re coming to the area."
United States
Angela
The price is ₩216,235
₩251,130 total
includes taxes & fees
Jul 27 - Jul 28
L' Eroico
Courtyard

I Parigi Corbinelli

I Parigi Corbinelli
Florence
9.6 out of 10, Exceptional, (168 reviews)
"Excelente "
Brazil
Osvaldo
The price is ₩138,744
₩172,525 total
includes taxes & fees
Jul 29 - Jul 30
I Parigi Corbinelli
Free daily buffet breakfast

Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (79 reviews)
"We had a wonderful experience! The staff was kind and very helpful. Our room was stunning and very spacious for a family of 5! The breakfast was amazing, and all of the activities on site were very fun - we especially enjoyed the cooking class! I would absolutely love to return here. I recommend looking into and booking on-site activities in advance so you can get the most out of your experience!"
United States
Julia
The price is ₩451,974
₩503,807 total
includes taxes & fees
Aug 2 - Aug 3
Terre di Baccio
Aerial view

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (36 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is ₩355,601
₩394,486 total
includes taxes & fees
Aug 7 - Aug 8
Riserva di Fizzano Residence
Aerial view

Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (72 reviews)
"Beautiful property"
Canada
Mary
The price is ₩254,475
₩293,193 total
includes taxes & fees
Aug 9 - Aug 10
Villa Curina Resort
Exterior

B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes

B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (27 reviews)
"The beautiful place, very comfortable, the incredible attention, the breakfast felt like in Homewith a lot of love We hope to return one day"
Mexico
Raymundo
The price is ₩165,113
₩188,261 total
includes taxes & fees
Aug 9 - Aug 10
B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes
Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas

Borgo di Erboli

Borgo di Erboli
Cavriglia
The price is ₩186,431
₩208,392 total
includes taxes & fees
Aug 18 - Aug 19
Borgo di Erboli
Property amenity

hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.4 out of 10, Very Good, (91 reviews)
"Good location. The bed and pillows not so good ! "
United States
Sebastian
The price is ₩88,087
₩101,873 total
includes taxes & fees
Aug 23 - Aug 24
hu Firenze Certosa camping in town
Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers

Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (36 reviews)
"Beautiful villa, very spacious, gorgeous property and great restaurant on the property to have a delicious meal. Staff very welcoming. Close to other main cities, like Siena, for day trips. We loved sitting by the pool, although it wasn’t heated, so too cold to use in April. We did love using the indoor heated pool and hot tub each day. We had a fabulous time and hope to go back someday! "
Canada
Jeremy
The price is ₩248,084
₩272,892 total
includes taxes & fees
Aug 4 - Aug 5
Villa di Sotto
Restaurant

Relais Villa Olmo

Relais Villa Olmo
Impruneta
9.4 out of 10, Exceptional, (252 reviews)
"Delightful location, comfortable bed, excellent food."
Canada
Rupert
The price is ₩285,843
₩319,405 total
includes taxes & fees
Aug 14 - Aug 15
Relais Villa Olmo
Breakfast, lunch and dinner served

La Locanda di Pietracupa

La Locanda di Pietracupa
Barberino Tavarnelle
9.6 out of 10, Exceptional, (38 reviews)
"Charming and very original. Great warmth from the staff and very helpful. Enjoyed the room and restaurant at and surrounding towns."
Australia
Con
The price is ₩250,719
₩282,427 total
includes taxes & fees
Jul 27 - Jul 28
La Locanda di Pietracupa
Outdoor dining

B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (83 reviews)
"It was a wonderful stay the bed was comfortable and the view was beautiful. "
United States
Ruben
The price is ₩193,412
₩219,389 total
includes taxes & fees
Jul 28 - Jul 29
B&B La Fonte del Machiavelli
Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers

Residenzia del Sogno

Residenzia del Sogno
Castellina in Chianti
9.6 out of 10, Exceptional, (15 reviews)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
The price is ₩186,249
₩211,510 total
includes taxes & fees
Jul 28 - Jul 29
Residenzia del Sogno
Property entrance

Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (102 reviews)
"This is an excellent property. Very historic, rustic and with great views across the Tuscan landscapes. Lorenzo and his mother were super duper hosts who took great care of us. The property dates back to 1380 and the rooms are decorated with choicest artifacts that adds greatly to the experience. The location is fantastic too with the local market and restaurants in easy walking reach. The breakfast service is fabulous with many choices and Lorenzo himself is great chef as well! Highly recommend...
United States
Nilesh
The price is ₩413,970
₩462,003 total
includes taxes & fees
Aug 4 - Aug 5
Villa il Fedino
Exterior

Hu Norcenni Girasole Village

Hu Norcenni Girasole Village
4.0 star property
Figline e Incisa Valdarno
8.6 out of 10, Excellent, (327 reviews)
"We all loved this place. It is conveniently close to Florence or Sienna so you can take a day trips if you get bored but there are plenty of activities on site. We wished we have reserved more days to stay but we will do that next year."
United States
Kalinka
The price is ₩163,892
₩185,258 total
includes taxes & fees
Jul 28 - Jul 29
Hu Norcenni Girasole Village
Panoramic Apartment (2) | Terrace/patio

Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
8.8 out of 10, Excellent, (3 reviews)
"Staff was very helpful. Was a bit bummed the pool was closed as that was part of the reason for choosing the hotel. "
United States
Jeffrey
The price is ₩177,933
₩205,679 total
includes taxes & fees
Aug 21 - Aug 22
Casa Vacanze Squarcialupi
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

Salvadonica - Borgo del Chianti

Salvadonica - Borgo del Chianti

10/10 Excellent
"This is the Tuscan escape you dream about! We absolutely loved our stay at Salvadonica! A peaceful retreat surrounded by vineyards, hills, and incredible sunsets! It’s perfectly situated to explore Chianti and other locations nearby. The restored farmhouse offers wonderful accommodations that are comfortable and private. There’s a refreshing pool, outdoor movies, yoga in the vineyard, and plenty of spaces to escape and relax. The onsite restaurant La Volpenera, was casually elegant and delicious! Try the gelato with the Salvadonica olive oil…you won’t be sorry. The included breakfast buffet featured a variety of options and was perfect start to each day. We signed up for the Wine and Olive Oil Tasting with Sommelier Irene which gave us a personalized tasting of Salvedonica’s products and history. Excellent experience! And we took the Cooking Class with Chef Ivana which was the best meal we had on our entire trip! Cooking with Ivana felt like we were spending the day with family! Everyone working here provided exceptional service! I only wish we had a longer stay! Can’t wait to return to Salvadonica!"
Maria 2-night trip
Posted 2 days ago
Salvadonica - Borgo del Chianti

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