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
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

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
Outdoor dining

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
Exterior

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
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 €99
includes taxes & fees
13 Sept - 14 Sept
Fullino Nero
Property grounds

7. 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
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 €174
includes taxes & fees
8 Sept - 9 Sept
Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti
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 €174
includes taxes & fees
8 Sept - 9 Sept
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

The Social Hub Florence Lavagnini

The Social Hub Florence Lavagnini

8/10 Good
"I have stayed at the Social Hub twice and it is a clean, modern hotel within easy walking distance to the historic center and Santa Maria Novella Train Station. Conveniently, there is also a tram stop right in front of the hotel that goes directly to the airport. The staff are always incredibly kind and helpful."
Jeffrey 3-night trip
Posted 2 hours ago
The Social Hub Florence Lavagnini

Find out more about Castellina in Chianti

Castellina in Chianti Cottages information

Number of reviews
54
Accommodation
122 Cottages
Lowest Price
€99
Highest Price
€99

Frequently asked questions

How much do cottages in Castellina in Chianti cost?
Expect to pay between €99 and €99 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 122 cottages in Castellina in Chianti. Whether you're travelling 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 travelling 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 favourite 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.