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

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Our top choices for Chianti Region cottages

1. Casa il Cipresso, in the heart of Chianti with swimming pool

Casa il Cipresso, in the heart of Chianti with swimming pool
Castellina in Chianti
10.0 out of 10, Exceptional, (2 reviews)
"Maurizio was an excellent host, he was very helpful in explaining the house and amenities during the check in process, and also sent us a lot of references for food shopping, restaurants, wineries and things to do while in Tuscany.I highly recommend this property."
United States
Guillermo A.
Casa il Cipresso, in the heart of Chianti with swimming pool

2. La Misura, cottage with garden and swimming pool on the hills of Chianti

La Misura, cottage with garden and swimming pool on the hills of Chianti
Castellina in Chianti
10.0 out of 10, Exceptional, (2 reviews)
"What a beautiful stay in the enchanting Tuscan countryside! Every detail was attended to and we could not have felt more at home. We can only dream of returning sometime!"
United States
Jami B.
La Misura, cottage with garden and swimming pool on the hills of Chianti

3. The independent Capannina on the Tuscan hills

The independent Capannina on the Tuscan hills
Toscana
10.0 out of 10, Exceptional, (2 reviews)
"The perfect Tuscan holiday, the perfect location to explore the surrounding attractions and come back to a comfortable home on the hill. Colle is very close, has everything we were looking for without the crowds. The bed is very comfortable, the bathroom perfectly set up. The kitchen has what is needed, but could do with a few more bowls, platters, spices oil. Best to bring that along.Our hosts were very friendly and with great communication.We highly recommend this beautiful little house!...
United States
Regina A.
The independent Capannina on the Tuscan hills

4. Casa Antico Roseto - cottage with swimming pool

Casa Antico Roseto - cottage with swimming pool
Castellina in Chianti
8.8 out of 10, Excellent, (3 reviews)
"The borgo was perfect for our family of 6 adults. The views from the pool were spectacular. We had what we needed in kitchen and we grilled one night. The stone structure set on mountainside gave natural coolness for comfort with amazing views- even from the shower! There is AC which we didn’t use but good idea for peak summer. We walked to a great restaurant and also walked to winery for wine tasting. We shared the property but it felt private with our own outdoor dining areas. Maurizio was...
United States
Lisa S.
Casa Antico Roseto - cottage with swimming pool

5. La Quercia, apartment with garden for 6/8 people in the heart of Chianti

La Quercia, apartment with garden for 6/8 people in the heart of Chianti
Montespertoli
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful 7 day stay. The location is perfect. It is an easy drive to all the towns in Tuscany. The property is beautiful and quiet. The views are amazing. Patrizia was a great host and very helpful with restaurant and winery recommendations."
United States
Mark S.
La Quercia, apartment with garden for 6/8 people in the heart of Chianti

6. Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (56 reviews)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
The price is SAR 404
SAR 462 total
includes taxes & fees
7 Oct - 8 Oct
Fullino Nero

7. Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti

Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti
Monteaperti
10.0 out of 10, Exceptional, (3 reviews)
"We loved this place. Modern cabin set in a rustic Tuscan setting. Beautiful property, very comfortable stay, and very attentive staff. Family owned and operated. Amazing restaurant just steps away. A perfect place for respite"
United States
Ian F.
The price is SAR 683
SAR 781 total
includes taxes & fees
8 Oct - 9 Oct
Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti

8. Pettirosso c/o Le Mascie

Pettirosso c/o Le Mascie
Sovicille
Pettirosso c/o Le Mascie

9. Rondine c/o Le Mascie

Rondine c/o Le Mascie
Sovicille
The price is SAR 939
SAR 948 total
includes taxes & fees
13 Oct - 14 Oct
Rondine c/o Le Mascie

10. Batticoda c/o Le Mascie

Batticoda c/o Le Mascie
Sovicille
The price is SAR 1,405
SAR 1,413 total
includes taxes & fees
15 Oct - 16 Oct
Batticoda c/o Le Mascie

11. Cardellino c/o Le Mascie

Cardellino c/o Le Mascie
Sovicille
The price is SAR 1,405
SAR 1,413 total
includes taxes & fees
5 Oct - 6 Oct
Cardellino c/o Le Mascie

12. Apartment in Chianti with pool ID 3939

Apartment in Chianti with pool ID 3939
Sovicille
The price is SAR 1,405
SAR 1,413 total
includes taxes & fees
7 Oct - 8 Oct
Apartment in Chianti with pool ID 3939

13. Apartment in Chianti with pool ID 453

Apartment in Chianti with pool ID 453
Sovicille
The price is SAR 1,405
SAR 1,413 total
includes taxes & fees
5 Oct - 6 Oct
Apartment in Chianti with pool ID 453

14. Capinera c/o Le Mascie

Capinera c/o Le Mascie
Sovicille
Capinera c/o Le Mascie

15. Merlo c/o Le Mascie - Two Bedroom Cottage, Sleeps 4

Merlo c/o Le Mascie - Two Bedroom Cottage, Sleeps 4
Sovicille
The price is SAR 1,405
SAR 1,413 total
includes taxes & fees
2 Oct - 3 Oct
Merlo c/o Le Mascie - Two Bedroom Cottage, Sleeps 4
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