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

Chianti Region Holiday Rentals

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Our top choices for Chianti Region holiday rentals

1. 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 S$428
includes taxes & fees
24 Aug - 25 Aug
Terre di Baccio

2. Relais Villa Olmo

Relais Villa Olmo
Impruneta
9.4 out of 10, Exceptional, (262 reviews)
"Delightful location, comfortable bed, excellent food."
Canada
Rupert
The price is S$270
includes taxes & fees
30 Aug - 31 Aug
Relais Villa Olmo

3. Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (48 reviews)
"This place was beautiful, quiet like a picture you’d see in the movies"
Canada
Nadia
The price is S$146
includes taxes & fees
23 Aug - 24 Aug
Villa San Filippo

4. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (117 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
The price is S$116
includes taxes & fees
1 Sept - 2 Sept
Chianti Village Morrocco

5. 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 S$294
includes taxes & fees
24 Aug - 25 Aug
Riserva di Fizzano Residence

6. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (73 reviews)
"Beautiful property"
Canada
Mary
The price is S$242
includes taxes & fees
20 Sept - 21 Sept
Villa Curina Resort

7. 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 S$173
includes taxes & fees
20 Sept - 21 Sept
B&B La Fonte del Machiavelli

8. 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 S$392
includes taxes & fees
8 Sept - 9 Sept
Villa il Fedino

9. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (38 reviews)
"Great spot"
Canada
Philippe
The price is S$226
includes taxes & fees
10 Sept - 11 Sept
Villa di Sotto

10. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (24 reviews)
"A very peaceful and relaxing B&B that I highly recommend, spacious rooms , clean and well maintained! Host were very pleasing and helpful… definitely recommend!!"
Canada
Sabatino
The price is S$229
includes taxes & fees
23 Aug - 24 Aug
Borgo Argenina

11. 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 S$168
includes taxes & fees
2 Sept - 3 Sept
B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes

12. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (100 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is S$162
includes taxes & fees
2 Sept - 3 Sept
Palazzo Pacini

13. 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 S$168
includes taxes & fees
22 Aug - 23 Aug
I Parigi Corbinelli

14. hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.4 out of 10, Very good, (97 reviews)
"Lovely location in the hills. Really nice pool and bar."
United Kingdom
Jessica
The price is S$77
includes taxes & fees
23 Aug - 24 Aug
hu Firenze Certosa camping in town

15. Borgo di Erboli

Borgo di Erboli
Cavriglia
The price is S$178
includes taxes & fees
1 Sept - 2 Sept
Borgo di Erboli

16. L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (15 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 S$225
includes taxes & fees
23 Aug - 24 Aug
L' Eroico

17. Villa Il Palagio

Villa Il Palagio
Rignano sull'Arno
8.8 out of 10, Excellent, (77 reviews)
"Our family of five enjoyed our time at the property very much. The rooms were comfortable and the surrounding area is beautiful. The pool is a huge plus to cool down and have a relaxing time. The Rignano train station nearby makes it easy to get around Italy, by connecting to Florence’s main station. Truly an asset. The A1 highway is also nearby connecting you within easy access to beautiful Tuscany. Restaurants in the area were very good also. I would definitely stay again at Vila Il...
United States
Nuno
The price is S$140
includes taxes & fees
13 Sept - 14 Sept
Villa Il Palagio

18. 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 S$136
includes taxes & fees
21 Aug - 22 Aug
Mariani Bed & Breakfast

19. 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 S$245
includes taxes & fees
21 Aug - 22 Aug
La Locanda di Pietracupa

20. Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (85 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is S$248
includes taxes & fees
6 Sept - 7 Sept
Antico Borgo il Cardino
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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