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
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Chianti Region vacation rentals

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

1. Relais Villa Olmo - Place of Charme

Relais Villa Olmo - Place of Charme
Impruneta
9.6 out of 10, Exceptional, (277 reviews)
"Great property and staff. Highly recommend!"
United States
Michael
The price is P5,659
P6,435 total
includes taxes & fees
Nov 26 - Nov 27
Relais Villa Olmo - Place of Charme
A table with breakfast items and a view of rolling hills.

2. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Tavarnelle Val di Pesa
8.6 out of 10, Excellent, (122 reviews)
"Superb property. Nice and quiet atmosphere. We enjoyed a lot. Definitely will come again."
United States
Nirav
The price is P3,953
P4,489 total
includes taxes & fees
Nov 13 - Nov 14
Chianti Village Morrocco
An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

3. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.6 out of 10, Exceptional, (104 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is P7,300
P8,171 total
includes taxes & fees
Dec 12 - Dec 13
Palazzo Pacini
An aerial view of a hotel with a swimming pool, outdoor seating area, and well-maintained gardens.

4. 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 P5,421
P7,647 total
includes taxes & fees
Dec 2 - Dec 3
Antica Pieve B&B
A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

5. 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 P16,316
P18,229 total
includes taxes & fees
Nov 13 - Nov 14
Terre di Baccio
A courtyard with a stone building featuring an arched entrance, potted plants, and outdoor seating.

6. I Parigi Corbinelli

I Parigi Corbinelli
Florence
9.6 out of 10, Exceptional, (175 reviews)
"Fabulous breakfast, wonderful views from breakfast room and garden. Very helpful staff, suggesting local restaurants and things to do."
United Kingdom
Susan
The price is P4,763
P6,082 total
includes taxes & fees
Nov 13 - Nov 14
I Parigi Corbinelli
A water park with a pool, slides, and a wooden deck area.

7. hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.6 out of 10, Excellent, (128 reviews)
"Very helpful staff and comfortable affordable stay"
United States
Ana María
The price is P3,014
P3,525 total
includes taxes & fees
Dec 8 - Dec 9
hu Firenze Certosa camping in town
A stone building with a yellow sign reading "b&b erioico".

8. 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 P8,082
P9,451 total
includes taxes & fees
Dec 12 - Dec 13
L' Eroico
A dining area with a table set for two, featuring a view of greenery through a window.

9. 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 P9,088
P10,278 total
includes taxes & fees
Nov 24 - Nov 25
La Locanda di Pietracupa
A traditional interior with stone arches, a staircase, and a cozy seating area with a table.

10. 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 P8,044
P9,130 total
includes taxes & fees
Nov 13 - Nov 14
Agriturismo La Ferrozzola
A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

11. 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 P7,198
P8,339 total
includes taxes & fees
Nov 16 - Nov 17
Casa Vacanze Squarcialupi
A swimming pool with lounge chairs and umbrellas, surrounded by stone walls and a landscaped area with trees.

12. 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 P6,657
P7,428 total
includes taxes & fees
Dec 9 - Dec 10
Relais Villa Belvedere
A swimming pool with a stone fountain, surrounded by a grassy area and trees.

13. Rocca Palazzaccio

Rocca Palazzaccio
3.0 star property
Impruneta
9.2 out of 10, Wonderful, (15 reviews)
"A lovely stay at this property with our 2 year old.The apartment had everything we needed and communication with the host was very good There are steep hills to access the property by car or foot so bear that in mind but we managed fine with a pram and a car its just worth noting Handy to have laundry facilities on site aswell. There is a coop just a few minutes down the road Lovely views and a clean pool which was perfect for our little one to use and toys there that he could play in the...
United Kingdom
Lauren
The price is P3,311
P12,555 total
includes taxes & fees
Nov 15 - Nov 16
Rocca Palazzaccio
An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

14. B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (94 reviews)
"The view is unique. Perfect location for a romantic trip."
United States
Stella
The price is P7,286
P8,295 total
includes taxes & fees
Nov 13 - Nov 14
B&B La Fonte del Machiavelli
A cozy living room with a stone wall, a wine rack, and two sofas.

15. Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (27 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is P6,011
P6,612 total
includes taxes & fees
Nov 13 - Nov 14
Villa Cassia di Baccano
An arched entrance with a lantern above, flanked by two potted plants.

16. Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (109 reviews)
"Food was amazing, we love how quiet and relaxing it was"
United States
Justyna
The price is P10,030
P11,314 total
includes taxes & fees
Nov 23 - Nov 24
Villa il Fedino
A courtyard with a fountain, a pergola with flowers, and a building with a bell tower.

17. 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 P10,162
P11,178 total
includes taxes & fees
Nov 16 - Nov 17
Relais Villa Belpoggio - Residenza d'Epoca
A balcony with a table and chairs, a railing, and a view of a town and hills.

18. Residence Il Connubio

Residence Il Connubio
3.0 star property
Impruneta
8.8 out of 10, Excellent, (38 reviews)
"Great location if you are looking for a place quiet, great outdoor scenery. Pleasant people. "
United States
Damian
The price is P4,751
P5,437 total
includes taxes & fees
Nov 14 - Nov 15
Residence Il Connubio
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

Il Borro - Relais & Châteaux

Il Borro - Relais & Châteaux

10/10 Excellent
"Excellent unique property with top notch service, attention and experiences. The food and staff at Osteria Il Borro were exceptional!"
Kelly 2-night trip
Posted 4 days ago
Il Borro - Relais & Châteaux

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