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
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Chianti Region cottages

Exterior

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, (1 review)
"Beautiful setting with a rustic and friendly vibe. The place was clean and well-kept. We enjoyed every minute! A bonus was that the nights were cool (did t need the AC), and we slept with the windows open, despite the heat during the day."
Canada
Jon M.
Casa il Cipresso, in the heart of Chianti with swimming pool
Exterior

2. 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
Exterior

3. CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL

CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL
Castellina in Chianti
10.0 out of 10, Exceptional, (1 review)
"Lovely visit. The views are amazing. "
United States
lyndon s.
CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL
Property grounds

4. 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
Outdoor dining

5. Casa Belvedere cottage with swimming pool in the heart of Chianti

Casa Belvedere cottage with swimming pool in the heart of Chianti
Castellina in Chianti
Casa Belvedere cottage with swimming pool in the heart of Chianti
Property grounds

6. Il Melograno, Chianti apartment in farmhouse for 4 people with garden

Il Melograno, Chianti apartment in farmhouse for 4 people with garden
Montespertoli
Il Melograno, Chianti apartment in farmhouse for 4 people with garden
Studio, Patio, Ground Floor | Terrace/patio

7. Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (54 reviews)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
The price is £93
includes taxes & fees
12 Aug - 13 Aug
Fullino Nero
Exterior

8. 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 £148
includes taxes & fees
7 Aug - 8 Aug
Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti
Exterior

9. Charming double bedroom in cottage in enchanting Monteaperti with WiFi, AC

Charming double bedroom in cottage in enchanting Monteaperti with WiFi, AC
Monteaperti
10.0 out of 10, Exceptional, (1 review)
"This place was fantastic! What a gem. The bed was comfy, the AC was cold, the bathroom was perfect. We shared the cottage with another couple we were traveling with. The bedroom doors open up to a shared living area, the front entrance is through the main indoor dining area.We had breakfast outside each morning. It was perfect. The staff here is just so nice and considerate, a true family affair. A flight of stairs leads down to a lovely restaurant with plentiful outside dining that shouldn't be...
United States
Cary W.
The price is £146
includes taxes & fees
6 Aug - 7 Aug
Charming double bedroom in cottage in enchanting Monteaperti with WiFi, AC
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

Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent
"Just an amazing overall experience, super welcoming and hospitable staff. Vacationing in an estate that is 1100 years old makes it even more memorable. Thank you Spaltena"
Ashley 2-night trip
Posted 22 hours ago
Castello di Spaltenna- Small Luxury Hotels of the World

Find out more about Chianti Region

Chianti Region Cottages information

Number of reviews
65
Accommodation
29 Cottages
Lowest Price
£93
Highest Price
£148

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