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

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Chianti Region holiday rentals

A stone building with a patio area featuring a table and chairs under a large umbrella.

1. Relais Villa Olmo - Place of Charme

Relais Villa Olmo - Place of Charme
Impruneta
9.6 out of 10, Exceptional, (273 reviews)
"Great property and staff. Highly recommend!"
United States
Michael
The price is 2.753.653 ₫
3.115.860 ₫ total
includes taxes & fees
13 Nov - 14 Nov
Relais Villa Olmo - Place of Charme
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, (81 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
The price is 3.780.217 ₫
4.274.027 ₫ total
includes taxes & fees
25 Oct - 26 Oct
Villa Curina Resort
A stone building with a garden in front.

3. 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 4.599.944 ₫
5.291.514 ₫ total
includes taxes & fees
25 Oct - 26 Oct
Borgo Argenina
A room with a window featuring sheer curtains, a radiator below, and a view of a green landscape.

4. 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 2.374.971 ₫
2.728.257 ₫ total
includes taxes & fees
27 Oct - 28 Oct
Mariani Bed & Breakfast
A balcony with a view of rolling hills, a table with a book and a bottle, and a chair.

5. 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 2.167.590 ₫
2.558.338 ₫ total
includes taxes & fees
28 Oct - 29 Oct
Villa San Filippo
A table with breakfast items and a view of rolling hills.

6. 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 2.193.367 ₫
2.470.597 ₫ total
includes taxes & fees
26 Oct - 27 Oct
Chianti Village Morrocco
A two-story house with a patio area, potted plants, and outdoor furniture.

7. 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 3.749.796 ₫
4.240.448 ₫ total
includes taxes & fees
22 Nov - 23 Nov
La Locanda di Pietracupa
A hot tub with two glasses of a beverage.

8. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (40 reviews)
"Great spot"
Canada
Philippe
The price is 4.600.297 ₫
5.060.326 ₫ total
includes taxes & fees
29 Oct - 30 Oct
Villa di Sotto
A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

9. 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 3.126.278 ₫
3.612.588 ₫ total
includes taxes & fees
7 Nov - 8 Nov
Casa Vacanze Squarcialupi
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
9.0 out of 10, Wonderful, (77 reviews)
"True Tuscan style, beautiful views and a lovely breakfast."
Canada
Janet
The price is 2.803.845 ₫
3.127.650 ₫ total
includes taxes & fees
25 Oct - 26 Oct
Relais Villa Belvedere
A bedroom with a stone wall, a large mirror, a bed with white linens, a potted plant, and a view through a window with curtains.

11. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (81 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 7.010.441 ₫
7.827.273 ₫ total
includes taxes & fees
13 Nov - 14 Nov
Terre di Baccio
A tented room with a bed, curtains, and a view of an outdoor deck.

12. hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.6 out of 10, Excellent, (121 reviews)
"Friendly staff!"
United States
larisa
The price is 1.243.406 ₫
1.454.587 ₫ total
includes taxes & fees
25 Oct - 26 Oct
hu Firenze Certosa camping in town
A courtyard with a stone building featuring an arched entrance, potted plants, and outdoor seating.

13. I Parigi Corbinelli

I Parigi Corbinelli
Florence
9.6 out of 10, Exceptional, (172 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 1.961.029 ₫
2.504.495 ₫ total
includes taxes & fees
3 Nov - 4 Nov
I Parigi Corbinelli
A stone building with a yellow sign reading "b&b erioico".

14. 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 3.334.459 ₫
3.899.481 ₫ total
includes taxes & fees
2 Nov - 3 Nov
L' Eroico
A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.

15. 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 3.427.047 ₫
3.885.744 ₫ total
includes taxes & fees
25 Oct - 26 Oct
Residenzia del Sogno
An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

16. B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (91 reviews)
"The view is unique. Perfect location for a romantic trip."
United States
Stella
The price is 2.999.963 ₫
3.415.747 ₫ total
includes taxes & fees
26 Oct - 27 Oct
B&B La Fonte del Machiavelli
An arched entrance with a lantern above, flanked by two potted plants.

17. 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 4.588.760 ₫
5.163.424 ₫ total
includes taxes & fees
23 Nov - 24 Nov
Villa il Fedino
A courtyard with a fountain, a pergola with flowers, and a building with a bell tower.

18. 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 4.184.291 ₫
4.602.720 ₫ total
includes taxes & fees
26 Oct - 27 Oct
Relais Villa Belpoggio - Residenza d'Epoca
A stone building with a wooden porch, a table with wine glasses and fruit, and a car parked in the background.

19. Teranga in Chianti - Parking & Garden 3 BR

Teranga in Chianti - Parking & Garden 3 BR
Tavarnelle Val di Pesa
The price is 2.524.969 ₫
10.130.008 ₫ total
includes taxes & fees
30 Oct - 31 Oct
Teranga in Chianti - Parking & Garden 3 BR
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 Villa Cesi

Hotel Villa Cesi

10/10 Excellent
"Rooms are very clean and staff are very friendly and super helpful and above all they are caring and very accommodating especially with our elderly less abled parents for which we are very grateful. Property is in a beautiful setting. Restaurant staff also very helpful. Thank you very much to all who hosted us at Villa Cesi."
Anshi 2-night trip
Posted 6 days ago
Hotel Villa Cesi