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Our top choices for Chianti Region holiday rentals

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 ฿2,526
฿3,006 total
includes taxes & fees
29 Jun - 30 Jun
Villa San Filippo

Borgo di Erboli

Borgo di Erboli
Cavriglia
The price is ฿3,631
฿4,070 total
includes taxes & fees
16 Jul - 17 Jul
Borgo di Erboli

Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (69 reviews)
"This was our second stay. The property is beautiful and our room was lovely. The breakfast was one of the best on our trip in Italy."
Canada
Dr Anne
The price is ฿5,689
฿6,562 total
includes taxes & fees
28 Jun - 29 Jun
Villa Curina Resort

Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (23 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is ฿5,586
฿6,145 total
includes taxes & fees
2 Jul - 3 Jul
Villa Cassia di Baccano

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 ฿4,101
฿4,662 total
includes taxes & fees
12 Jul - 13 Jul
B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes

Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (100 reviews)
"This is a lovely gem. Includes parking which is hard to find. Family owned and its a truly beautiful place. Breakfast was amazing as well!! Recommend!! "
United States
rose
The price is ฿9,065
฿10,123 total
includes taxes & fees
29 Jun - 30 Jun
Villa il Fedino

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (32 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is ฿7,566
฿8,399 total
includes taxes & fees
2 Jul - 3 Jul
Riserva di Fizzano Residence

Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (34 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 ฿5,672
฿6,240 total
includes taxes & fees
5 Jul - 6 Jul
Villa di Sotto

Relais Villa Olmo

Relais Villa Olmo
Impruneta
9.4 out of 10, Exceptional, (247 reviews)
"Delightful location, comfortable bed, excellent food."
Canada
Rupert
The price is ฿6,407
฿7,162 total
includes taxes & fees
22 Jul - 23 Jul
Relais Villa Olmo

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 ฿2,628
฿2,966 total
includes taxes & fees
8 Jul - 9 Jul
Chianti Village Morrocco

I Parigi Corbinelli

I Parigi Corbinelli
Florence
9.6 out of 10, Exceptional, (168 reviews)
"Charming place, great welcoming"
United Kingdom
Stefano
The price is ฿2,860
฿3,602 total
includes taxes & fees
29 Jun - 30 Jun
I Parigi Corbinelli

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 ฿4,422
฿5,016 total
includes taxes & fees
28 Jun - 29 Jun
B&B La Fonte del Machiavelli

Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (99 reviews)
"A nice blend of old world charm and modern conveniences. It is far from "
United States
John
The price is ฿5,057
฿5,639 total
includes taxes & fees
8 Jul - 9 Jul
Palazzo Pacini

Residence Il Connubio

Residence Il Connubio
3.0 star property
Impruneta
9.0 out of 10, Wonderful, (34 reviews)
"Great location if you are looking for a place quiet, great outdoor scenery. Pleasant people. "
United States
Damian
The price is ฿3,204
฿3,639 total
includes taxes & fees
19 Jul - 20 Jul
Residence Il Connubio

Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (76 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 ฿10,334
฿11,520 total
includes taxes & fees
9 Jul - 10 Jul
Terre di Baccio

Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
The price is ฿1,676
฿1,919 total
includes taxes & fees
28 Jun - 29 Jun
Sportland

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 ฿3,117
฿3,581 total
includes taxes & fees
1 Jul - 2 Jul
Mariani Bed & Breakfast

Hu Norcenni Girasole Village

Hu Norcenni Girasole Village
4.0 star property
Figline e Incisa Valdarno
8.6 out of 10, Excellent, (321 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 ฿2,503
฿2,867 total
includes taxes & fees
8 Jul - 9 Jul
Hu Norcenni Girasole Village

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 ฿4,944
฿5,742 total
includes taxes & fees
1 Jul - 2 Jul
L' Eroico

Villa Il Palagio

Villa Il Palagio
Rignano sull'Arno
8.6 out of 10, Excellent, (64 reviews)
"Very friendly staff. Great breakfast! In alla very nice!"
Sweden
martin
The price is ฿3,049
฿3,506 total
includes taxes & fees
28 Jul - 29 Jul
Villa Il Palagio
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

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