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

Chianti Region Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Chianti Region holiday rentals

A table with breakfast items and a view of rolling hills.

1. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Tavarnelle Val di Pesa
8.6 out of 10, Excellent, (121 reviews)
"It’s seen its best day a while ago. Basic necessities for an overnight, but I wouldn’t choose it again."
United States
Winonah
The price is HK$572
HK$647 total
includes taxes & fees
14 Oct - 15 Oct
Chianti Village Morrocco
A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

2. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (39 reviews)
"Great spot"
Canada
Philippe
The price is HK$1,225
HK$1,704 total
includes taxes & fees
1 Oct - 2 Oct
Villa di Sotto
A villa with a swimming pool, outdoor seating, and a tennis court.

3. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (80 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
The price is HK$1,322
HK$1,490 total
includes taxes & fees
27 Sept - 28 Sept
Villa Curina Resort
A stone building with a garden in front.

4. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (27 reviews)
"What an amazing place. We enjoyed it so much."
United States
Tatevik
The price is HK$1,356
HK$1,563 total
includes taxes & fees
28 Sept - 29 Sept
Borgo Argenina
A kitchen with wooden cabinets, a glass display case, and a dining area with a table and chairs.

5. Mariani Bed & Breakfast

Mariani Bed & Breakfast
Castellina in Chianti
9.8 out of 10, Exceptional, (18 reviews)
"Beautiful view, very clean and everything in great condition. Friendly service. We will definitely stay again."
United States
Frank
The price is HK$694
HK$799 total
includes taxes & fees
7 Oct - 8 Oct
Mariani Bed & Breakfast
A spacious indoor area with arched windows, wooden furniture, and hanging plants.

6. Relais Villa Olmo

Relais Villa Olmo
Impruneta
9.4 out of 10, Exceptional, (267 reviews)
"Very friendly and clean."
United States
Mohamed
The price is HK$1,303
HK$1,460 total
includes taxes & fees
11 Oct - 12 Oct
Relais Villa Olmo
An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

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, (85 reviews)
"Beautiful location, beautiful rooms. Host is very friendly and accommodating."
Australia
James
The price is HK$925
HK$1,053 total
includes taxes & fees
4 Oct - 5 Oct
B&B La Fonte del Machiavelli
A courtyard with a fountain, a pergola with flowers, and a building with a bell tower.

8. Relais Villa Belpoggio - Residenza d'Epoca

Relais Villa Belpoggio - Residenza d'Epoca
Loro Ciuffenna
9.8 out of 10, Exceptional, (35 reviews)
"Excellent getaway- beautiful property - great staff - extremely clean - I give it a 100"
United Kingdom
Mona
The price is HK$1,290
HK$1,419 total
includes taxes & fees
29 Sept - 30 Sept
Relais Villa Belpoggio - Residenza d'Epoca
A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

9. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (80 reviews)
"Amazing property. Air conditioning works. Dinner and breakfast is first class. Free parking"
United States
SYDNEY
The price is HK$4,320
HK$4,787 total
includes taxes & fees
27 Sept - 28 Sept
Terre di Baccio
A courtyard with a stone building featuring an arched entrance, potted plants, and outdoor seating.

10. I Parigi Corbinelli

I Parigi Corbinelli
Florence
9.6 out of 10, Exceptional, (170 reviews)
"Beautiful setting, stunning views, incredible pool and gardens and so easy to jump on the bus into the city."
United Kingdom
Jacqui
The price is HK$836
HK$1,027 total
includes taxes & fees
23 Oct - 24 Oct
I Parigi Corbinelli
A swimming pool with lounge chairs and umbrellas, surrounded by stone walls and a landscaped area with trees.

11. Relais Villa Belvedere

Relais Villa Belvedere
Figline e Incisa Valdarno
9.2 out of 10, Wonderful, (75 reviews)
"True Tuscan style, beautiful views and a lovely breakfast."
Canada
Janet
The price is HK$864
HK$964 total
includes taxes & fees
17 Oct - 18 Oct
Relais Villa Belvedere
A stone building with a yellow sign reading "b&b erioico".

12. 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 HK$1,262
HK$1,460 total
includes taxes & fees
5 Oct - 6 Oct
L' Eroico
A water park with a pool, slides, and a wooden deck area.

13. hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.4 out of 10, Very good, (107 reviews)
"Lovely location in the hills. Really nice pool and bar."
United Kingdom
Jessica
The price is HK$383
HK$448 total
includes taxes & fees
7 Oct - 8 Oct
hu Firenze Certosa camping in town
A stone building with a courtyard, a swimming pool, and vineyard fields in the background.

14. Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (39 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is HK$1,572
HK$1,747 total
includes taxes & fees
29 Sept - 30 Sept
Riserva di Fizzano Residence
An arched entrance with a lantern above, flanked by two potted plants.

15. Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (105 reviews)
"Tha parking was easy on the property. It was within walking distance to the villages with shops, restaurants and cafes. The best part was the staff. The owners were incredibly helpful, friendly and made you feel like family. Breakfast outside was lovely overlooking the hills of Tuscany. We met many people and had lovely conversations with other travelers during breakfast. A gem in Tuscany."
United States
Lori
The price is HK$1,951
HK$2,181 total
includes taxes & fees
17 Oct - 18 Oct
Villa il Fedino
A dining area with a table set for two, featuring a view of greenery through a window.

16. La Locanda di Pietracupa

La Locanda di Pietracupa
Tavarnelle Val di Pesa
9.6 out of 10, Exceptional, (38 reviews)
"Great place, wonderful restaurant"
Germany
Isabell
The price is HK$1,349
HK$1,519 total
includes taxes & fees
1 Oct - 2 Oct
La Locanda di Pietracupa
A balcony with a view of rolling hills, a table with a book and a bottle, and a chair.

17. Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Val d'Elsa
8.6 out of 10, Excellent, (53 reviews)
"This place was beautiful, quiet like a picture you’d see in the movies"
Canada
Nadia
The price is HK$745
HK$873 total
includes taxes & fees
25 Oct - 26 Oct
Villa San Filippo
A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.

18. 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 HK$1,002
HK$1,138 total
includes taxes & fees
7 Oct - 8 Oct
Residenzia del Sogno

19. 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, (28 reviews)
"Me and my girlfriend really did enjoy this property. Both host were very friendly and welcoming to us. We both did enjoy the feel at Home environment. We would definitely come back here on a future trip. Big shout out to the host for the wonderful cook meals. Great to know a bit about them as well."
United States
Erick
The price is HK$862
HK$984 total
includes taxes & fees
8 Oct - 9 Oct
B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes
A cozy living room with a stone wall, a wine rack, and two sofas.

20. Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (26 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is HK$1,015
HK$1,473 total
includes taxes & fees
10 Oct - 11 Oct
Villa Cassia di Baccano
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

Fattoria di Vegi

Fattoria di Vegi

10/10 Excellent
"This is a newly renovated and opened property cared for by a wonderful family. Everything has been taken care of down to the last detail. The food is delicious, the rooms are well appointed and till we thoroughly enjoyed exploring the property and every interesting nook! There's lots to do including a ping pong table and a beautiful pool. My only regret was not staying longer"
Patrick 2-night trip
Posted 1 day ago
Fattoria di Vegi

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