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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 1.967.925 ₫
2.346.737 ₫ total
includes taxes & fees
15 Jun - 16 Jun
Villa San Filippo

Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (66 reviews)
"Great stay but can feel a bit captive to their restaurant for dinner. Min 2 courses mandatory per person and dessert doesn’t count "
Canada
Shelley
The price is 3.633.699 ₫
4.239.822 ₫ total
includes taxes & fees
21 Jun - 22 Jun
Villa Curina Resort

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 5.994.205 ₫
6.654.298 ₫ total
includes taxes & fees
10 Jun - 11 Jun
Riserva di Fizzano Residence

Relais Villa Olmo

Relais Villa Olmo
Impruneta
9.4 out of 10, Exceptional, (244 reviews)
"We had an excellent stay, the staff is very friendly, stunning location and easy but windy road into Florence "
United States
Juliana
The price is 3.410.368 ₫
3.842.414 ₫ total
includes taxes & fees
24 Jun - 25 Jun
Relais Villa Olmo

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 7.570.322 ₫
8.448.700 ₫ total
includes taxes & fees
7 Jun - 8 Jun
Villa il Fedino

Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (33 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 4.199.542 ₫
4.619.496 ₫ total
includes taxes & fees
18 Jun - 19 Jun
Villa di Sotto

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 3.003.308 ₫
3.303.639 ₫ total
includes taxes & fees
22 Jun - 23 Jun
Villa Cassia di Baccano

B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (82 reviews)
"It was a wonderful stay the bed was comfortable and the view was beautiful. "
United States
Ruben
The price is 3.536.954 ₫
4.011.995 ₫ total
includes taxes & fees
7 Jun - 8 Jun
B&B La Fonte del Machiavelli

Residence Il Connubio

Residence Il Connubio
3.0 star property
Impruneta
8.8 out of 10, Excellent, (32 reviews)
"Such a cute little place! Very clean and easy to get around! Would highly recommend!"
United States
Desiree
The price is 2.703.280 ₫
3.064.617 ₫ total
includes taxes & fees
28 Jun - 29 Jun
Residence Il Connubio

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 3.204.632 ₫
3.646.441 ₫ total
includes taxes & fees
18 Jun - 19 Jun
B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes

Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (75 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 8.265.302 ₫
9.213.179 ₫ total
includes taxes & fees
14 Jun - 15 Jun
Terre di Baccio

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 4.494.206 ₫
5.004.300 ₫ total
includes taxes & fees
19 Jun - 20 Jun
Palazzo Pacini

Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (113 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
The price is 2.335.134 ₫
2.629.320 ₫ total
includes taxes & fees
7 Jun - 8 Jun
Chianti Village Morrocco

I Parigi Corbinelli

I Parigi Corbinelli
Florence
9.6 out of 10, Exceptional, (167 reviews)
"Charming place, great welcoming"
United Kingdom
Stefano
The price is 2.587.974 ₫
3.210.809 ₫ total
includes taxes & fees
8 Jun - 9 Jun
I Parigi Corbinelli

L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (13 reviews)
"Monica was the friendliest most enthusiastic host we’ve stayed with. Everything from her greeting to the amazing breakfast was perfect. She does a lot of baking, so the breakfast was really a treat and you could also get eggs cooked in various ways. The room was a little small but very comfortable. Parking was on the street, but it was fairly close and easy."
United States
Perry
The price is 3.954.314 ₫
4.592.438 ₫ total
includes taxes & fees
1 Jul - 2 Jul
L' Eroico

Hu Norcenni Girasole Village

Hu Norcenni Girasole Village
4.0 star property
Figline e Incisa Valdarno
8.6 out of 10, Excellent, (319 reviews)
"Beautiful place for family "
Canada
Ismail
The price is 1.569.911 ₫
1.817.911 ₫ total
includes taxes & fees
7 Jun - 8 Jun
Hu Norcenni Girasole Village

Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (82 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is 4.398.784 ₫
4.990.344 ₫ total
includes taxes & fees
30 Jun - 1 Jul
Antico Borgo il Cardino

Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (23 reviews)
"Such a beautiful place to stay! The cottage was amazing, very spacious and clean. The grounds themselves were picturesque, was well above our expectations and the host was very welcoming and accommodating."
United Kingdom
Sasha
The price is 4.820.737 ₫
5.545.502 ₫ total
includes taxes & fees
7 Jun - 8 Jun
Borgo Argenina

hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.2 out of 10, Very good, (72 reviews)
"Good location. The bed and pillows not so good ! "
United States
Sebastian
The price is 1.405.791 ₫
1.637.258 ₫ total
includes taxes & fees
11 Jun - 12 Jun
hu Firenze Certosa camping in town

Antica Pieve B&B

Antica Pieve B&B
Barberino Tavarnelle
9.4 out of 10, Exceptional, (14 reviews)
"Very nice stay here! Great breakfast and coffee every morning. Great location to tour around to different wineries and towns. Free parking. "
Canada
Jessica
The price is 3.723.192 ₫
4.823.495 ₫ total
includes taxes & fees
7 Jul - 8 Jul
Antica Pieve B&B
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