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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Castellina in Chianti cottages

A stone building with a pathway leading to it, surrounded by trees and greenery.

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
A stone building with a small entrance, a chimney, and a view of green hills.

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
A rustic outdoor dining area with a stone wall, wooden furniture, and potted plants.

3. 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
An aerial view of a rural estate with a large building, a swimming pool, and surrounding vegetation.

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
A stone building with a rustic entrance, a small patio area with outdoor furniture, and a wooden fence in the foreground.

5. 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
$108 nightly
The price is $123
Sep 30 - Oct 1
Total with taxes and fees
Fullino Nero
A stone house with a tiled roof, two windows, and a door.

6. 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
A stone building with a gravel path, potted plants, and a large vase with flowers.

7. 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
A stone house with a tiled roof, a patio with a table and chairs, surrounded by trees and a grassy field.

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.
$208 nightly
The price is $214
Oct 8 - Oct 9
Total with taxes and fees
Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti
A rustic stone building with a tiled roof, surrounded by lush greenery and a clear sky.

9. Rondine c/o Le Mascie

Rondine c/o Le Mascie
Sovicille
$250 nightly
The price is $252
Oct 4 - Oct 5
Total with taxes and fees
Rondine c/o Le Mascie
A rustic stone building with a tiled roof, surrounded by lush greenery and a clear sky.

10. Pettirosso c/o Le Mascie

Pettirosso c/o Le Mascie
Sovicille
$500 nightly
The price is $503
Sep 30 - Oct 1
Total with taxes and fees
Pettirosso c/o Le Mascie
A rustic stone building with a tiled roof, surrounded by lush greenery and a clear sky.

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

Merlo c/o Le Mascie - Two Bedroom Cottage, Sleeps 4
Sovicille
$375 nightly
The price is $378
Oct 2 - Oct 3
Total with taxes and fees
Merlo c/o Le Mascie - Two Bedroom Cottage, Sleeps 4
A stone patio with a table and a vase of flowers.

12. Apartment in Chianti with pool ID 3939

Apartment in Chianti with pool ID 3939
Sovicille
$375 nightly
The price is $378
Oct 7 - Oct 8
Total with taxes and fees
Apartment in Chianti with pool ID 3939
A rustic stone building with a tiled roof, surrounded by lush greenery and a clear sky.

13. Capinera c/o Le Mascie

Capinera c/o Le Mascie
Sovicille
$500 nightly
The price is $503
Sep 30 - Oct 1
Total with taxes and fees
Capinera c/o Le Mascie
A rustic stone building with a tiled roof, surrounded by lush greenery and a clear sky.

14. Apartment in Chianti with pool ID 453

Apartment in Chianti with pool ID 453
Sovicille
$375 nightly
The price is $378
Oct 5 - Oct 6
Total with taxes and fees
Apartment in Chianti with pool ID 453
A rustic stone building with a tiled roof, surrounded by lush greenery and a clear sky.

15. Batticoda c/o Le Mascie

Batticoda c/o Le Mascie
Sovicille
$375 nightly
The price is $378
Oct 12 - Oct 13
Total with taxes and fees
Batticoda c/o Le Mascie
A rustic stone building with a tiled roof, surrounded by lush greenery and a clear sky.

16. Cardellino c/o Le Mascie

Cardellino c/o Le Mascie
Sovicille
$375 nightly
The price is $378
Oct 4 - Oct 5
Total with taxes and fees
Cardellino c/o Le Mascie
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

Hotel Albani Firenze

Hotel Albani Firenze

10/10 Excellent
"We thoroughly enjoyed our stay. The room was impeccable. Beautiful! The staff was very helpful. Breakfast was delicious. Our dinner was wonderful. The location was an easy walk 15-20 minutes to about everything."
Kim 4-night trip
Posted 3 hours ago
Hotel Albani Firenze

Find out more about Castellina in Chianti

Castellina in Chianti Cottages information

Number of reviews
71
Accommodation
130 Cottages
Lowest Price
$123
Highest Price
$503

Frequently asked questions

How much do cottages in Castellina in Chianti cost?
Expect to pay between $123 and $503 per night for cottages in Castellina in Chianti. No matter your budget, an epic stay is a click away on Expedia. These prices were 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?
Take your pick of 130 cottages in Castellina in Chianti. Whether you're traveling with the little ones or planning a weekend break with your besties, Expedia can help you find the perfect place to escape the hustle and bustle.
Are there any family-friendly cottages in Castellina in Chianti?
You bet there are! Book a room at Fullino Nero, a terrific base for exploring the great outdoors in Castellina in Chianti. This family-friendly cottage has a 2-star rating and includes conveniences like laundry facilities and pillow top mattresses. Once you've checked in and dropped off your bags, there are plenty of family-friendly attractions to visit around Castellina in Chianti. Monteriggioni Castle and Castello di Albola promise fun for all ages.
Why book your cottage in Castellina in Chianti with Expedia?
We think that traveling should be easy, so if you're after cottages in Castellina in Chianti at the perfect price, Expedia can help. Save those pennies and go for a thrifty option far away from the downtown buzz, or book an upmarket cottage to really spoil your favorite people.
How can I find cheap cottages in Castellina in Chianti?
A wonderful way to track down cheap cottages in Castellina in Chianti is with Expedia's useful filter tool. Narrow your search by star rating, budget and amenities to snag awesome bargains in just a few clicks.
What is there to do in Castellina in Chianti near my cottage?
You'll find loads of fun things to do and see in Castellina in Chianti. Discover leading attractions like Buondonno Winery, City Hall Castellina In Chianti and Casa Vinicola Luigi Cecchi. Walls of Monteriggioni, Castellina Fortress and Archaeological Museum of Chianti are also on many to-do lists.

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