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

Chianti Region Vacation Rentals

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Chianti Region holiday rentals

A villa with a swimming pool, outdoor seating, and a tennis court.

1. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (82 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
The price is RM535
RM607 total
includes taxes & fees
30 Oct - 31 Oct
Villa Curina Resort
A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

2. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (82 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 RM1,101
RM1,229 total
includes taxes & fees
6 Nov - 7 Nov
Terre di Baccio
A spacious indoor area with arched windows, wooden furniture, and hanging plants.

3. Relais Villa Olmo - Place of Charme

Relais Villa Olmo - Place of Charme
Impruneta
9.6 out of 10, Exceptional, (274 reviews)
"Great property and staff. Highly recommend!"
United States
Michael
The price is RM379
RM430 total
includes taxes & fees
29 Nov - 30 Nov
Relais Villa Olmo - Place of Charme
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, (57 reviews)
"This place was beautiful, quiet like a picture you’d see in the movies"
Canada
Nadia
The price is RM399
RM466 total
includes taxes & fees
30 Oct - 31 Oct
Villa San Filippo
An arched entrance with a lantern above, flanked by two potted plants.

5. Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (108 reviews)
"Food was amazing, we love how quiet and relaxing it was"
United States
Justyna
The price is RM649
RM732 total
includes taxes & fees
27 Nov - 28 Nov
Villa il Fedino
A stone building with a garden in front.

6. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (28 reviews)
"What an amazing place. We enjoyed it so much."
United States
Tatevik
The price is RM766
RM879 total
includes taxes & fees
31 Oct - 1 Nov
Borgo Argenina
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, (92 reviews)
"The view is unique. Perfect location for a romantic trip."
United States
Stella
The price is RM471
RM536 total
includes taxes & fees
30 Oct - 31 Oct
B&B La Fonte del Machiavelli
A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

8. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (40 reviews)
"Great spot"
Canada
Philippe
The price is RM685
RM754 total
includes taxes & fees
30 Oct - 31 Oct
Villa di Sotto
A table with breakfast items and a view of rolling hills.

9. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Tavarnelle Val di Pesa
8.6 out of 10, Excellent, (121 reviews)
"Superb property. Nice and quiet atmosphere. We enjoyed a lot. Definitely will come again."
United States
Nirav
The price is RM355
RM399 total
includes taxes & fees
6 Nov - 7 Nov
Chianti Village Morrocco
A dining area with a table set for two, featuring a view of greenery through a window.

10. La Locanda di Pietracupa

La Locanda di Pietracupa
Tavarnelle Val di Pesa
9.4 out of 10, Exceptional, (40 reviews)
"Great place, wonderful restaurant"
Germany
Isabell
The price is RM589
RM666 total
includes taxes & fees
7 Nov - 8 Nov
La Locanda di Pietracupa
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
9.6 out of 10, Exceptional, (103 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is RM546
RM609 total
includes taxes & fees
1 Nov - 2 Nov
Palazzo Pacini
A traditional interior with stone arches, a staircase, and a cozy seating area with a table.

12. Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9 reviews)
"Very nice agriturismo. "
United States
Ruth
The price is RM520
RM590 total
includes taxes & fees
28 Nov - 29 Nov
Agriturismo La Ferrozzola
A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.

13. Residenzia del Sogno

Residenzia del Sogno
Castellina in Chianti
9.8 out of 10, Exceptional, (16 reviews)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
The price is RM538
RM610 total
includes taxes & fees
30 Oct - 31 Oct
Residenzia del Sogno
A water park with a pool, slides, and a wooden deck area.

14. hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.6 out of 10, Excellent, (122 reviews)
"Very helpful staff and comfortable affordable stay"
United States
Ana María
The price is RM195
RM228 total
includes taxes & fees
13 Nov - 14 Nov
hu Firenze Certosa camping in town
A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

15. Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
9.2 out of 10, Wonderful, (5 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 RM466
RM540 total
includes taxes & fees
29 Nov - 30 Nov
Casa Vacanze Squarcialupi
A swimming pool with lounge chairs and umbrellas, surrounded by stone walls and a landscaped area with trees.

16. Relais Villa Belvedere

Relais Villa Belvedere
Figline e Incisa Valdarno
9.0 out of 10, Wonderful, (77 reviews)
"True Tuscan style, beautiful views and a lovely breakfast."
Canada
Janet
The price is RM433
RM484 total
includes taxes & fees
29 Nov - 30 Nov
Relais Villa Belvedere
A kitchen with wooden cabinets, a glass display case, and a dining area with a table and chairs.

17. 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 RM373
RM429 total
includes taxes & fees
30 Oct - 31 Oct
Mariani Bed & Breakfast
A stone building with a yellow sign reading "b&b erioico".

18. 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 RM524
RM613 total
includes taxes & fees
2 Nov - 3 Nov
L' Eroico
A courtyard with a stone building featuring an arched entrance, potted plants, and outdoor seating.

19. I Parigi Corbinelli

I Parigi Corbinelli
Florence
9.6 out of 10, Exceptional, (173 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 RM308
RM393 total
includes taxes & fees
4 Nov - 5 Nov
I Parigi Corbinelli
A courtyard with a fountain, a pergola with flowers, and a building with a bell tower.

20. Relais Villa Belpoggio - Residenza d'Epoca

Relais Villa Belpoggio - Residenza d'Epoca
Loro Ciuffenna
9.8 out of 10, Exceptional, (36 reviews)
"We had fantastic time here! The property is so beautiful and special! The views are stunning and the breakfast was very delicious! Hope we will come again! Special thanks to Tania who was very friendly and nice all the time!"
Germany
Kristina
The price is RM658
RM724 total
includes taxes & fees
1 Nov - 2 Nov
Relais Villa Belpoggio - Residenza d'Epoca
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

Hotel Borgo di Cortefreda Relais - Place of Charme

Hotel Borgo di Cortefreda Relais - Place of Charme

8/10 Good
"It was a beautiful place. Location was perfect to travel around. It was very clean. Restaurant is decent and food was good. Breakfast was ok."
Rahul 1-night trip
Posted 19 hours ago
Hotel Borgo di Cortefreda Relais - Place of Charme

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