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

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
9.4 out of 10, Exceptional, (269 reviews)
"Very friendly and clean."
United States
Mohamed
The price is ￥21,868
￥24,587 total
includes taxes & fees
Nov 8 - Nov 9
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, (80 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
The price is ￥17,076
￥19,492 total
includes taxes & fees
Oct 19 - Oct 20
Villa Curina Resort
A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

3. 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 ￥17,367
￥20,167 total
includes taxes & fees
Nov 11 - Nov 12
Casa Vacanze Squarcialupi
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, (56 reviews)
"This place was beautiful, quiet like a picture you’d see in the movies"
Canada
Nadia
The price is ￥14,435
￥16,943 total
includes taxes & fees
Oct 21 - Oct 22
Villa San Filippo
A dining area with a table set for two, featuring a view of greenery through a window.

5. 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 ￥20,674
￥23,451 total
includes taxes & fees
Nov 7 - Nov 8
La Locanda di Pietracupa
A stone building with a yellow sign reading "b&b erioico".

6. 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 ￥20,855
￥24,360 total
includes taxes & fees
Nov 2 - Nov 3
L' Eroico
A stone building with a garden in front.

7. 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 ￥26,952
￥31,066 total
includes taxes & fees
Oct 15 - Oct 16
Borgo Argenina
A table with breakfast items and a view of rolling hills.

8. 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 ￥13,370
￥15,063 total
includes taxes & fees
Oct 18 - Oct 19
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.

9. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (40 reviews)
"Great spot"
Canada
Philippe
The price is ￥27,771
￥30,549 total
includes taxes & fees
Oct 20 - Oct 21
Villa di Sotto
A stone building with a gated entrance, terracotta pots with flowers, and a staircase leading up to the door.

10. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Ruffoli
9.2 out of 10, Wonderful, (26 reviews)
"This is truly a unique and special property providing incredible value . One of the most beautiful views in a spectacular setting hidden away in the Tuscan hills above Panzano. A perfect location for day trips to vinyards, restaurants and the Chianti area. Our apartment was extremely well appointed and beautifully decorated. Spacious and varied outdoor sitting areas and patios with a very nice pool area. Our hostess Babette was extremely accomodating and informative which added to our overall...
Canada
James
The price is ￥14,318
￥28,149 total
includes taxes & fees
Oct 12 - Oct 13
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
A courtyard with a stone building featuring an arched entrance, potted plants, and outdoor seating.

11. 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 ￥12,013
￥15,342 total
includes taxes & fees
Nov 1 - Nov 2
I Parigi Corbinelli
A room with two beds, a wooden dresser, a painting, and a door.

12. Teranga in Chianti - Parking & Garden 3 BR

Teranga in Chianti - Parking & Garden 3 BR
Tavarnelle Val di Pesa
The price is ￥16,281
￥62,239 total
includes taxes & fees
Oct 12 - Oct 13
Teranga in Chianti - Parking & Garden 3 BR
A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

13. 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 ￥42,943
￥47,947 total
includes taxes & fees
Oct 30 - Oct 31
Terre di Baccio
An arched entrance with a lantern above, flanked by two potted plants.

14. 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 ￥34,403
￥38,552 total
includes taxes & fees
Oct 14 - Oct 15
Villa il Fedino
A stone building with a courtyard, a swimming pool, and vineyard fields in the background.

15. Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (42 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is ￥30,865
￥34,307 total
includes taxes & fees
Oct 19 - Oct 20
Riserva di Fizzano Residence
A water park with a pool, slides, and a wooden deck area.

16. hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.6 out of 10, Excellent, (116 reviews)
"Friendly staff!"
United States
larisa
The price is ￥6,627
￥7,822 total
includes taxes & fees
Oct 12 - Oct 13
hu Firenze Certosa camping in town
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 ￥13,782
￥15,870 total
includes taxes & fees
Oct 14 - Oct 15
Mariani Bed & Breakfast
An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

18. B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (88 reviews)
"Beautiful location, beautiful rooms. Host is very friendly and accommodating."
Australia
James
The price is ￥18,377
￥20,924 total
includes taxes & fees
Oct 13 - Oct 14
B&B La Fonte del Machiavelli
A dining table set with plates, glasses, and a bottle, with a view of a landscape through a window.

19. Panzano34 A Charming Loft in the Heart of Chianti

Panzano34 A Charming Loft in the Heart of Chianti
Greve in Chianti
The price is ￥14,793
￥23,720 total
includes taxes & fees
Oct 15 - Oct 16
Panzano34 A Charming Loft in the Heart of Chianti
A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.

20. 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 ￥25,147
￥28,370 total
includes taxes & fees
Oct 12 - Oct 13
Residenzia del Sogno
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

10/10 Excellent
"Great spot and friendly staff."
Chris 4-night trip
Posted 1 day ago
Villa I Barronci Resort & Spa

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