A stone building with a clock tower, steps leading up to it, and people walking around.

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Castellina in Chianti 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, (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
Exterior

2. 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
Exterior

3. 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
Outdoor dining

4. 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
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
Studio, Patio, Ground Floor | Terrace/patio

6. 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 AU$162
includes taxes & fees
30 Aug - 31 Aug
Fullino Nero
Exterior

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 AU$277
includes taxes & fees
26 Aug - 27 Aug
Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti
Property grounds

8. 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
Property grounds

9. 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
Exterior

10. 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 AU$277
includes taxes & fees
25 Aug - 26 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 Castellina in Chianti Hotel Reviews

Palazzo Montebello

Palazzo Montebello

10/10 Excellent
"Clean room, great and fast service, decent size rooms, highly recommend"
Tirath 2-night trip
Posted 4 hours ago
Palazzo Montebello

Find out more about Castellina in Chianti

Castellina in Chianti Cottages information

Number of reviews
68
Accommodation
135 Cottages
Lowest Price
AU$162
Highest Price
AU$277

Frequently asked questions

How much do cottages in Castellina in Chianti cost?
You can expect to pay between AU$162 and AU$277 per night for cottages in Castellina in Chianti. Whatever your budget, a wonderful stay is just a click or two away on Expedia. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Castellina in Chianti?
Claim your holiday time and pick from 135 cottages in Castellina in Chianti. Picturing a place where you can surround yourself with nature? Expedia will help you find the ideal property in just a click or two.
What is there to do in Castellina in Chianti near my cottage?
Castellina in Chianti has enough experiences and activities to keep you entertained for weeks (or months!), beginning with Monteriggioni Castle. Meleto Castle, Castello di Radda Winery and Castello di Albola are other wonderful attractions. If you're sticking around a while, Badia a Coltibuono and Isole e Olena Winery will put the finishing touches on your itinerary.

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