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
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Chianti Region holiday rentals

A spacious indoor area with arched windows, wooden furniture, and hanging plants.

1. Relais Villa Olmo

Relais Villa Olmo
Impruneta
9.4 out of 10, Exceptional, (268 reviews)
"Very friendly and clean."
United States
Mohamed
The price is S$188
includes taxes & fees
2 Nov - 3 Nov
Relais Villa Olmo
A villa with a swimming pool, outdoor seating, and a tennis court.

2. 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 S$169
includes taxes & fees
12 Oct - 13 Oct
Villa Curina Resort
A table with breakfast items and a view of rolling hills.

3. 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 S$108
includes taxes & fees
6 Oct - 7 Oct
Chianti Village Morrocco
A balcony with a view of rolling hills, a table with a book and a bottle, and a chair.

4. 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 S$108
includes taxes & fees
18 Oct - 19 Oct
Villa San Filippo
A stone building with a courtyard, a swimming pool, and vineyard fields in the background.

5. Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (41 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is S$260
includes taxes & fees
6 Oct - 7 Oct
Riserva di Fizzano Residence
A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

6. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (40 reviews)
"Great spot"
Canada
Philippe
The price is S$237
includes taxes & fees
12 Oct - 13 Oct
Villa di Sotto
A courtyard with a stone building featuring an arched entrance, potted plants, and outdoor seating.

7. 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 S$124
includes taxes & fees
1 Nov - 2 Nov
I Parigi Corbinelli
A kitchen with wooden cabinets, a glass display case, and a dining area with a table and chairs.

8. 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 S$129
includes taxes & fees
13 Oct - 14 Oct
Mariani Bed & Breakfast
A pool area with a water slide and a stage for performances.

9. Hu Norcenni Girasole Village

Hu Norcenni Girasole Village
4.0 star property
Figline e Incisa Valdarno
8.6 out of 10, Excellent, (333 reviews)
"Amazing venue , lots of kids entertainment. Lots of facilities- shops restaurants. Splash parks were brilliant. Highly recommended."
United Kingdom
Katie
Hu Norcenni Girasole Village
A swimming pool with lounge chairs and umbrellas, surrounded by stone walls and a landscaped area with trees.

10. 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 S$150
includes taxes & fees
8 Oct - 9 Oct
Relais Villa Belvedere
An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

11. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (102 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is S$214
includes taxes & fees
6 Oct - 7 Oct
Palazzo Pacini
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 S$194
includes taxes & fees
2 Nov - 3 Nov
L' Eroico
A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

13. Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
9.0 out of 10, Wonderful, (4 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 S$172
includes taxes & fees
4 Nov - 5 Nov
Casa Vacanze Squarcialupi
A dining area with a table set for two, featuring a view of greenery through a window.

14. La Locanda di Pietracupa

La Locanda di Pietracupa
Tavarnelle Val di Pesa
9.6 out of 10, Exceptional, (39 reviews)
"Great place, wonderful restaurant"
Germany
Isabell
The price is S$233
includes taxes & fees
1 Nov - 2 Nov
La Locanda di Pietracupa
An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

15. B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (87 reviews)
"Beautiful location, beautiful rooms. Host is very friendly and accommodating."
Australia
James
The price is S$170
includes taxes & fees
6 Oct - 7 Oct
B&B La Fonte del Machiavelli
A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.

16. 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 S$183
includes taxes & fees
6 Oct - 7 Oct
Residenzia del Sogno
A dining table set with plates, glasses, and a bottle, with a view of a landscape through a window.

17. Panzano34 A Charming Loft in the Heart of Chianti

Panzano34 A Charming Loft in the Heart of Chianti
Greve in Chianti
The price is S$207
includes taxes & fees
15 Oct - 16 Oct
Panzano34 A Charming Loft in the Heart of Chianti
An aerial view of a hotel with a swimming pool, outdoor seating area, and well-maintained gardens.

18. Antica Pieve B&B

Antica Pieve B&B
Tavarnelle Val di Pesa
9.4 out of 10, Exceptional, (15 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 S$207
includes taxes & fees
24 Oct - 25 Oct
Antica Pieve B&B
A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

19. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (80 reviews)
"Amazing property and room, only issue is it’s very understaffed so it’s hard to get anything without chasing down workers. They also don’t stay on the property so after like 11pm you’re on your own. Besides that it was a wonderful location and very peaceful."
United States
Gage
The price is S$389
includes taxes & fees
30 Oct - 31 Oct
Terre di Baccio
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

Villa I Barronci Resort & Spa

Villa I Barronci Resort & Spa

8/10 Good
"We quite enjoyed the heated pool and views. Thank you for having us."
Dianna 1-night trip
Posted 22 hours ago
Villa I Barronci Resort & Spa

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