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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Castellina in Chianti cottages

Exterior

House Il Cipresso in the heart of Chianti with swimming pool

House 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.
House Il Cipresso in the heart of Chianti with swimming pool
Exterior

OLIVE TREES HOUSE WITH POOL

OLIVE TREES HOUSE WITH POOL
Castellina in Chianti
OLIVE TREES HOUSE WITH POOL
Outdoor dining

Casa La Misura, garden and pool in the heart of Chianti

Casa La Misura, garden and pool in the heart 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.
Casa La Misura, garden and pool in the heart of Chianti
Exterior

Casa Antico Roseto with swimming pool in the heart of Chianti

Casa Antico Roseto with swimming pool in the heart of Chianti
Castellina in Chianti
8.0 out of 10, Very good, (2 reviews)
"The house was very charming 16th century stay. The gated patio off the bedroom was very convenient for morning coffee and evening wine. Such a beautiful countryside. The house is filled with antiques and furnishings, however, it’s time to update the mattresses. Taking the trash 6 minutes away to the indicated bins was a bit of an inconvenience as well. Very centrally located to Olive Oil and Chianti vineyards, a few towns from Panzano and Greece, gorgeous views and sunsets. "
United States
Brenna H.
Casa Antico Roseto with swimming pool in the heart of Chianti
Outdoor dining

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
Exterior

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, (2 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 NZ$366
includes taxes & fees
29 Apr - 30 Apr
Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti
Studio, Patio, Ground Floor | Terrace/patio

Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (50 reviews)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
The price is NZ$198
includes taxes & fees
29 Apr - 30 Apr
Fullino Nero
Exterior

Apartment in Chianti with pool ID 455

Apartment in Chianti with pool ID 455
Sovicille
Apartment in Chianti with pool ID 455
Exterior

Country House a Casole D'elsa ID 451

Country House a Casole D'elsa ID 451
Sovicille
Country House a Casole D'elsa ID 451
Property grounds

La Quercia, portion of farmhouse for 6/8 people with garden in the heart Chianti

La Quercia, portion of farmhouse for 6/8 people with garden in the heart 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, portion of farmhouse for 6/8 people with garden in the heart Chianti
Exterior

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.
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

Grand Hotel Baglioni

Grand Hotel Baglioni

10/10 Excellent
"Excellent location. Fantastic roof top terrace. Decent breakfast."
Steven 6-night trip
Posted 6 hours ago
Grand Hotel Baglioni

Find out more about Castellina in Chianti

Castellina in Chianti Cottages information

Number of reviews
10
Accommodation
134 Cottages
Lowest Price
NZ$198
Highest Price
NZ$366

Frequently asked questions

How much do cottages in Castellina in Chianti cost?
Expect to pay between NZ$198 and NZ$366 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 134 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.
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.