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Dec 7 - Dec 8
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Dec 8 - Dec 9
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Dec 12 - Dec 14
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Dec 19 - Dec 21

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Compare 15,227 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Restaurant
Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais

Castellina in Chianti
9.4 out of 10, Exceptional, (169)
"Wonderful setting."
United Kingdom
Simon
The price is ￥17,592
￥20,075 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Borgo di Pietrafitta Relais
Breakfast, lunch, dinner served; Italian cuisine, garden views
Castello di Fonterutoli Wine Resort

Castello di Fonterutoli Wine Resort

Castellina in Chianti
9.4 out of 10, Exceptional, (198)
"Clean room, courteous staff, and good winery"
United States
Sangchun
The price is ￥23,527
￥26,603 total
includes taxes & fees
Dec 8 - Dec 9
Castello di Fonterutoli Wine Resort
Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas, sun loungers
Hotel Colle Etrusco Salivolpi

Hotel Colle Etrusco Salivolpi

3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (112)
"Beautiful relaxing property. We wish we had more time to stay. "
United States
Wendi
The price is ￥21,529
￥24,225 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Hotel Colle Etrusco Salivolpi
Garden
Hotel Casafrassi Wine Resort

Hotel Casafrassi Wine Resort

4.0 star property
Castellina in Chianti
8.2 out of 10, Very Good, (215)
"Great place "
United States
Aloisio
Hotel Casafrassi Wine Resort
Seasonal outdoor pool
Agriturismo La Ferrozzola

Agriturismo La Ferrozzola

Castellina in Chianti
9.4 out of 10, Exceptional, (9)
"Very nice agriturismo. "
United States
Ruth
Agriturismo La Ferrozzola
Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers
Residenzia del Sogno

Residenzia del Sogno

Castellina in Chianti
9.8 out of 10, Exceptional, (14)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
The price is ￥21,373
￥24,234 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Residenzia del Sogno
Aerial view
Albergo Il Colombaio

Albergo Il Colombaio

3.0 star property
Castellina in Chianti
8.4 out of 10, Very Good, (58)
"I was a little hesitant about staying outside a "major city," but I'm so glad we did. Very cute hotel and room. It was a short walk to the local town, which had lots of options for dinner and chianti tasting. "
United States
Christine
The price is ￥20,642
￥23,249 total
includes taxes & fees
Dec 15 - Dec 16
Albergo Il Colombaio
Front of property
PODERE 1384

PODERE 1384

Castellina in Chianti
The price is ￥88,778
￥98,741 total
includes taxes & fees
Dec 13 - Dec 14
PODERE 1384
Panoramic Apartment, Hill View (4) | Terrace/patio
Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi

Castellina in Chianti
8.0 out of 10, Very Good, (2)
"Staff was very helpful. Was a bit bummed the pool was closed as that was part of the reason for choosing the hotel. "
United States
Jeffrey
The price is ￥18,069
￥20,961 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Casa Vacanze Squarcialupi
Seasonal outdoor pool
The Social Hub Florence Lavagnini

The Social Hub Florence Lavagnini

4.0 star property
San Lorenzo
9.0 out of 10, Wonderful, (1285)
"Super friendly staff! Great location! "
United States
Jutta
The price is ￥11,703
￥15,406 total
includes taxes & fees
Dec 14 - Dec 15
The Social Hub Florence Lavagnini
Outdoor spa tub
IQ Hotel Firenze

IQ Hotel Firenze

4.0 star property
Historic Centre of Florence
9.6 out of 10, Exceptional, (1080)
"Beautiful hotel! Great location! Amazing breakfast! Amazing staff! "
Canada
Blair
The price is ￥13,153
￥17,000 total
includes taxes & fees
Dec 9 - Dec 10
IQ Hotel Firenze
Front of property
Il Malaspina

Il Malaspina

4.0 star property
Historic Centre of Florence
10.0 out of 10, Exceptional, (5)
"Everything was perfect, cleanliness is top notch, staff is super helpful and friendly, Yehia is such a professional and nice guy. The hotel is super cozy and very central location!"
United States
Nadine
The price is ￥16,235
￥20,390 total
includes taxes & fees
Dec 8 - Dec 9
Il Malaspina
Terrace/patio
Hotel Athena

Hotel Athena

4.0 star property
Siena Historical Center
9.2 out of 10, Wonderful, (1003)
"Excellent hotel, very helpful staff, highly recommended "
United States
Vikram
The price is ￥14,139
￥16,096 total
includes taxes & fees
Dec 15 - Dec 16
Hotel Athena
Lobby
Hotel Chiusarelli

Hotel Chiusarelli

3.0 star property
Siena City Centre
8.8 out of 10, Excellent, (1001)
"Lovely staff and great location with a quiet, comfortable room."
United States
Katherine
The price is ￥14,844
￥16,871 total
includes taxes & fees
Dec 22 - Dec 23
Hotel Chiusarelli
Premium bedding, minibar, in-room safe, desk
Hotel Italia

Hotel Italia

3.0 star property
Camollia
9.2 out of 10, Wonderful, (1000)
"Great staff, wonderful breakfast, close to the plaza. "
United States
Izabela
The price is ￥11,098
￥12,751 total
includes taxes & fees
Dec 21 - Dec 22
Hotel Italia
Restaurant
Palazzo Ravizza

Palazzo Ravizza

4.0 star property
Siena Historical Center
9.4 out of 10, Exceptional, (745)
"We enjoyed our stay here."
United States
LAURIA
The price is ￥15,388
￥17,470 total
includes taxes & fees
Dec 8 - Dec 9
Palazzo Ravizza
Free daily buffet breakfast
Il Guelfo Bianco

Il Guelfo Bianco

Historic Centre of Florence
9.6 out of 10, Exceptional, (514)
"Great location, warm and accommodating staff. "
United States
Lisa
The price is ￥18,282
￥22,280 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Il Guelfo Bianco
Garden views, open daily
Globus Urban Hotel

Globus Urban Hotel

4.0 star property
Historic Centre of Florence
9.4 out of 10, Exceptional, (1053)
"Staff were very friendly and helpful. Short walk to train station and main attractions. Highly recommend to anyone visiting Florence."
Singapore
Wai Kong
The price is ￥21,965
￥26,693 total
includes taxes & fees
Dec 22 - Dec 23
Globus Urban Hotel
Lobby
Hotel La Fortezza

Hotel La Fortezza

3.0 star property
San Lorenzo
8.8 out of 10, Excellent, (922)
"Great hotel, amazing staff, rooms are new. Close to attractions "
United States
Milton
The price is ￥10,949
￥14,213 total
includes taxes & fees
Dec 16 - Dec 17
Hotel La Fortezza
Minibar, in-room safe, iron/ironing board, free WiFi
The Hoxton Florence

The Hoxton Florence

4.0 star property
Historic Centre of Florence
9.4 out of 10, Exceptional, (158)
"Lovely staff, nice ambience."
United Kingdom
James Robert
The price is ￥20,598
￥25,189 total
includes taxes & fees
Dec 21 - Dec 22
The Hoxton Florence
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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Stay near popular Castellina in Chianti attractions

Buondonno Winery

You can enjoy a tasting or tour at Buondonno Winery during your travels to Castellina in Chianti. Discover the beautiful countryside and wineries in this quaint area.
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Casa Vinicola Luigi Cecchi

You can enjoy a tasting or tour at Casa Vinicola Luigi Cecchi during your travels to Castellina in Chianti. Discover the beautiful countryside in this quaint area, or enjoy its local tours.
See properties

Learn more about Castellina in Chianti

Medieval stone buildings line the narrow streets where you'll find Tuscany's best wine shops and the fascinating Etruscan tomb museum. Climb the fortress tower for panoramic vineyard views, then join locals at Piazza del Comune for aperitivo hour with regional cheeses.

See all hotels in Castellina in Chianti
Castellina in Chianti which includes a church or cathedral, religious elements and heritage architecture

Top Castellina in Chianti Hotel Reviews

Hotel Paris

Hotel Paris

10/10 Excellent
"This place is great! They are generous with luggage storage times even after checkout and the room was beautiful. The showers are tiny but everywhere in italy is like that."
Matthew 1-night trip
Posted 20 hours ago
Hotel Paris

More cheap stays in Castellina in Chianti

Hotel Nuova Italia

Hotel Nuova Italia

Via Faenza 26 Florence FI
Get rates
8.2/10 Very Good! (827 reviews)

Frequently asked questions

What's the best place to stay in Castellina in Chianti?
Belvedere di San Leonino is a favorite with Expedia customers. This hotel offers a winery and a restaurant. Other favorite options based on reviews include Castello La Leccia and Hotel Colle Etrusco Salivolpi. See all available top hotels, or vacation rentals in Castellina in Chianti.
What are some of the best vacation rentals in Castellina in Chianti?
QK Costa58 Home Tower: This vacation home rental outside Castellina in Chianti is located in the historical district and offers a terrace, air-conditioning, and daily housekeeping to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Some other top choices in Castellina in Chianti are Farmhouse in the heart of the real chiantishire and Villa with large garden in the Chianti hills. See all vacation rentals in Castellina in Chianti.
If I need to cancel my hotel reservation in Castellina in Chianti, will I receive a refund?
Yes, most hotel reservations are fully refundable provided that you cancel before the hotel's cancellation deadline, which is often 24 or 48 hours before your scheduled arrival. If you booked a non-refundable reservation, you may still be able to cancel and be given a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Castellina in Chianti.
Where can I learn more about changing or cancelling my trip to Castellina in Chianti?
To access more information about changing or cancelling your trip to Castellina in Chianti, go to https://www.expedia.com/service/.
What's the best place to stay for a family trip to Castellina in Chianti?
Belvedere di San Leonino is a hotel with an outdoor pool and a restaurant, and it's a top choice on Expedia for families. Beautiful house on Chianti hilltop with exceptional views. is another good option for your family trip. Attractions in the area like Borgo di Vescine - Tenute di Castelvecchi and Siena Circuit are also fun for kids of all ages. Find more child-friendly accommodations in Castellina in Chianti.
What's the best pet-friendly place to stay in Castellina in Chianti?
Castello di Fonterutoli Wine Resort is a top B&B for people traveling with their pets, and offers a winery and a restaurant for its human guests. Two other good options to stay with your pet include Hotel Casafrassi Wine Resort and Borgo di Pietrafitta Relais. See more pet-friendly hotel accommodations in Castellina in Chianti.
Where is the best hotel to stay with easy access to Casa Vinicola Luigi Cecchi?
Adjacent to Casa Vinicola Luigi Cecchi, Albergo Il Colombaio is one of the top choices for your stay based on our traveler data, and this 3-star hotel offers free breakfast and a restaurant. Other good options close by include Villa Cristina and Mariani Bed & Breakfast.
What about the best place to stay near City Hall Castellina In Chianti?
One of the top choices for your stay is Mariani Bed & Breakfast, located next to City Hall Castellina In Chianti, and this townhouse offers free breakfast and free parking. Villa Cristina and Albergo Il Colombaio are other good choices nearby.
What's the best luxury place to stay in Castellina in Chianti?
Locanda le Piazze is a luxury hotel with a winery and a full-service spa, and it's a popular choice for Expedia travelers looking for an elegant place to stay. Find more luxury hotels in Castellina in Chianti.
What are some accommodations with pools in Castellina in Chianti?
IQ Hotel Firenze: Hotel, 12-minute walk from Cathedral of Santa Maria del Fiore. Features a full-service spa, a seasonal outdoor pool, and a sauna. Another option with an onsite pool is The Social Hub Florence Lavagnini. View all hotels with pools in Castellina in Chianti.
What is the best spa hotel in Castellina in Chianti?
Castello La Leccia is a top spa hotel featuring a bar and a restaurant. Treat yourself to a massage, steam room, or sauna at the onsite spa. Other popular spa hotels in Castellina in Chianti include Locanda le Piazze and Palazzo Squarcialupi. See all spa hotels in Castellina in Chianti.
What's the best accommodation near Peretola Airport (FLR)?
Hotel Cosmopolitan is a popular 4-star hotel featuring free WiFi and a bar. It's located a short 0.7 mi (1.2 km) from Peretola Airport. Other good choices close to the airport are Best Western Plus CHC Florence and Hotel Mirage.
What is staying in Castellina in Chianti like?
Visitors to Castellina in Chianti are sure to enjoy the wineries. Tourists can also enjoy so much more including its forests. In Castellina in Chianti, there are 277 hotels and other accommodations to choose from. Find out more about Castellina in Chianti.
What should I see while I'm in Castellina in Chianti?
Landmarks like Castellina Fortress, Walls of Monteriggioni, and Montecalvario might be worth a visit. Wine tasting is a great activity, and Buondonno Winery is one place to visit. A couple of additional sights to add to your agenda are City Hall Castellina In Chianti and Casa Vinicola Luigi Cecchi. Check out what more to see and do in Expedia's Castellina in Chianti guide.
What's the weather like in Castellina in Chianti?
The hottest months are usually August and July with an average temp of 72°F, while the coldest months are January and February with an average of 44°F. Average annual precipitation for Castellina in Chianti is 37 inches.

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