Find hotels in Castellina in Chianti from ฿2,384

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24 Dec - 25 Dec
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25 Dec - 26 Dec
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26 Dec - 28 Dec
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2 Jan - 4 Jan

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Our top choices for Castellina in Chianti hotels

Restaurant
Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
9.4 out of 10, Exceptional, (169)
Set amidst Castellina in Chianti, this family-friendly farm stay features an attached winery and refreshing outdoor pool. Enjoy complimentary WiFi and parking while exploring nearby Casa Vinicola Luigi Cecchi and Castellina Fortress, or unwind with massages and garden views.
"Wonderful setting."
United Kingdom
Simon
The price is ฿2,863
฿3,295 total
includes taxes & fees
6 Jan - 7 Jan 2026
Borgo di Pietrafitta Relais
Breakfast, lunch, dinner served; Italian cuisine, garden views
Castello di Fonterutoli Wine Resort

Castello di Fonterutoli Wine Resort

Castello di Fonterutoli Wine Resort
Castellina in Chianti
9.4 out of 10, Exceptional, (201)
Experience Tuscan charm at this wine resort with an attached winery and Osteria di Fonterutoli restaurant serving Italian cuisine. Located in Castellina in Chianti near Mazzei Winery and Walls of Monteriggioni, guests love the helpful staff.
"Amazing experience all around! Stayed for 2 nights!"
Canada
Matthew
The price is ฿5,074
฿5,728 total
includes taxes & fees
25 Dec - 26 Dec
Castello di Fonterutoli Wine Resort
Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas, pool loungers
Hotel Colle Etrusco Salivolpi

Hotel Colle Etrusco Salivolpi

Hotel Colle Etrusco Salivolpi
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (114)
"Friendly staff and walking distance to town"
United States
Scott
Hotel Colle Etrusco Salivolpi
Seasonal outdoor pool
Agriturismo La Ferrozzola

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
Panoramic Apartment, Hill View (4) | Terrace/patio
Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
8.0 out of 10, Very good, (2)
Experience authentic Tuscany at this apartment featuring free WiFi and parking. A tranquil garden and terrace enhance your stay while exploring nearby Archaeological Museum of Chianti and Castellina Fortress. Apartments include convenient refrigerators and microwaves.
"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 ฿3,783
฿4,381 total
includes taxes & fees
8 Jan - 9 Jan 2026
Casa Vacanze Squarcialupi
Aerial view
Albergo Il Colombaio

Albergo Il Colombaio

Albergo Il Colombaio
3.0 star property
Castellina in Chianti
8.4 out of 10, Very good, (58)
This charming hotel offers a serene escape with an inviting outdoor pool and garden terrace. Enjoy complimentary breakfast before exploring nearby Casa Vinicola Luigi Cecchi and Castellina Fortress. Unwind with evening drinks at the bar after a day of Tuscan adventure.
"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 ฿4,494
฿5,053 total
includes taxes & fees
26 Dec - 27 Dec
Albergo Il Colombaio
Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, pool loungers
Residenzia del Sogno

Residenzia del Sogno

Residenzia del Sogno
Castellina in Chianti
9.8 out of 10, Exceptional, (14)
Immerse yourself in the Chianti countryside at this charming affittacamere. Enjoy a swim in the seasonal outdoor pool, then unwind with drinks at the bar. Free WiFi and parking make exploring nearby Casa Vinicola Luigi Cecchi and Castellina Fortress convenient.
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
The price is ฿4,770
฿5,394 total
includes taxes & fees
2 Jan - 3 Jan 2026
Residenzia del Sogno
Front of property
PODERE 1384

PODERE 1384

PODERE 1384
Castellina in Chianti
The price is ฿17,977
฿19,995 total
includes taxes & fees
13 Jan - 14 Jan 2026
PODERE 1384
Seasonal outdoor pool
The Social Hub Florence Lavagnini

The Social Hub Florence Lavagnini

The Social Hub Florence Lavagnini
4.0 star property
San Lorenzo
9.0 out of 10, Wonderful, (1287)
Soak in city views from the seasonal outdoor pool at this modern hotel with a rooftop terrace. Just a 15-minute walk to Gallery of the Academy and 3 minutes from the tram. Enjoy 2 bars, a fitness centre, and praised breakfast before exploring nearby Uffizi Gallery.
"Super friendly staff! Great location! "
United States
Jutta
The price is ฿2,370
฿3,119 total
includes taxes & fees
6 Jan - 7 Jan 2026
The Social Hub Florence Lavagnini
Superior Room, Balcony | Balcony
Orto De Medici Hotel

Orto De Medici Hotel

Orto De Medici Hotel
4.0 star property
Historic Centre of Florence
9.6 out of 10, Exceptional, (1003)
"We had a wonderful time staying and close to a lot of wonderful spots to visit. "
United States
JoAnn
The price is ฿3,636
฿4,513 total
includes taxes & fees
11 Jan - 12 Jan 2026
Orto De Medici Hotel
Outdoor spa tub
IQ Hotel Firenze

IQ Hotel Firenze

IQ Hotel Firenze
4.0 star property
Historic Centre of Florence
9.6 out of 10, Exceptional, (1099)
Experience Florentine charm near Cathedral of Santa Maria del Fiore. This hotel offers a seasonal outdoor pool, poolside bar, and full-service spa with sauna and hot tub. Enjoy Italian cuisine at i'Qortile restaurant, just a 5-minute walk from San Marco University Tram Stop.
"Friendly staff, clean rooms, no issues with anything."
United States
Gonzalo
The price is ฿3,236
฿4,073 total
includes taxes & fees
18 Jan - 19 Jan 2026
IQ Hotel Firenze
Terrace/patio
Hotel Athena

Hotel Athena

Hotel Athena
4.0 star property
Siena Historical Center
9.2 out of 10, Wonderful, (1003)
This business-friendly hotel offers a scenic rooftop terrace, free WiFi, and complimentary parking. Guests praise the delicious breakfast and attentive staff. Sample local cuisine at Mangia restaurant, relax at the bar, or visit nearby National Museum of Archaeology.
"Excellent hotel, very helpful staff, highly recommended "
United States
Vikram
The price is ฿2,755
฿3,141 total
includes taxes & fees
15 Jan - 16 Jan 2026
Hotel Athena
Rooftop terrace
Villa del Sole Siena

Villa del Sole Siena

Villa del Sole Siena
Siena City Centre
9.8 out of 10, Exceptional, (627)
This business-friendly hotel offers free breakfast and WiFi near All'Orto de' Pecci and Piazza del Mercato. Enjoy drinks at the bar or snacks from the deli before relaxing in the garden. Guests consistently praise the exceptionally helpful staff.
"Beautiful small hotel with an exceptional staff. "
United States
Raymond
The price is ฿4,724
฿5,307 total
includes taxes & fees
11 Jan - 12 Jan 2026
Villa del Sole Siena
Premium bedding, minibar, in-room safe, desk
Hotel Italia

Hotel Italia

Hotel Italia
3.0 star property
Camollia
9.2 out of 10, Wonderful, (1001)
Experience Siena from this convenient hotel near the train station. Enjoy hiking and mountain biking trails nearby, plus visit Porta Camollia and Siena Stadium. Relax at the bar or on the terrace after exploring. Guests consistently praise the helpful staff and morning breakfast.
"Great staff, wonderful breakfast, close to the plaza. "
United States
Izabela
The price is ฿2,067
฿2,384 total
includes taxes & fees
15 Jan - 16 Jan 2026
Hotel Italia
Lobby
Hotel Chiusarelli

Hotel Chiusarelli

Hotel Chiusarelli
3.0 star property
Siena City Centre
8.8 out of 10, Excellent, (1000)
Charming hotel with a restaurant and garden terrace near Stadio Artemio Franchi. Enjoy the complimentary breakfast before exploring nearby Fontebranda. The attentive staff ensures a comfortable stay while room service and free WiFi add convenience.
"The room was spotlessly clean, the staff were welcoming and helpful, and the breakfast was delicious!"
United States
Kenneth
The price is ฿2,820
฿3,213 total
includes taxes & fees
9 Jan - 10 Jan 2026
Hotel Chiusarelli
Restaurant
Palazzo Ravizza

Palazzo Ravizza

Palazzo Ravizza
4.0 star property
Siena Historical Center
9.4 out of 10, Exceptional, (750)
Located near Pinacoteca Nazionale, this Siena hotel offers free WiFi, room service, and a tranquil terrace garden. Just minutes from the National Museum of Archaeology, guests rave about the delicious breakfast and attentive staff.
"We enjoyed our stay here."
United States
LAURIA
The price is ฿3,272
฿3,710 total
includes taxes & fees
6 Jan - 7 Jan 2026
Palazzo Ravizza
Exterior detail
Art Hotel Villa Agape

Art Hotel Villa Agape

Art Hotel Villa Agape
4.0 star property
Oltrarno
9.8 out of 10, Exceptional, (1000)
Set in a charming Tuscan villa, this hotel offers a tranquil garden escape just 15 minutes from Piazzale Michelangelo. Enjoy regional cuisine at the restaurant, sip wine at the bar, and take in city views from the rooftop terrace, all while staying close to Uffizi Gallery.
"A beautiful hotel, extremely clean and with stunning gardens."
United Kingdom
Elizabeth
The price is ฿3,760
฿4,650 total
includes taxes & fees
7 Jan - 8 Jan 2026
Art Hotel Villa Agape
Lobby
Hotel Horto Convento

Hotel Horto Convento

Hotel Horto Convento
4.0 star property
Historic Centre of Florence
9.8 out of 10, Exceptional, (603)
Discover this Art Deco hotel near Pitti Palace, offering a lush garden and daily buffet breakfast. Enjoy the bar/lounge, snack bar, and room service while being just minutes from Ponte Vecchio and Santa Maria Novella station.
"Excellent stay"
United States
Renata
The price is ฿3,890
฿4,793 total
includes taxes & fees
7 Jan - 8 Jan 2026
Hotel Horto Convento
Executive Suite (Jacuzzi) | Down duvets, memory-foam beds, minibar, in-room safe
Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio
4.0 star property
Historic Centre of Florence
8.8 out of 10, Excellent, (954)
"Nice, clean room. Good location and walkable"
United States
Shawn Dee
Hotel La Scaletta Al Ponte Vecchio
Lobby
Hotel La Fortezza

Hotel La Fortezza

Hotel La Fortezza
3.0 star property
San Lorenzo
8.8 out of 10, Excellent, (926)
"Great hotel, amazing staff, rooms are new. Close to attractions "
United States
Milton
The price is ฿2,367
฿3,043 total
includes taxes & fees
11 Jan - 12 Jan 2026
Hotel La Fortezza
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.
See properties

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 heritage architecture, religious elements and a church or cathedral

Top Castellina in Chianti Hotel Reviews

Grand Hotel Baglioni

Grand Hotel Baglioni

10/10 Excellent
"Impressive hotel, loved the mini bar, room very clean. The device provided in the room for exploring the city looked amazing - unfortunately ours wouldn’t charge so don’t know how good this was. We did let reception know and they said the next day we would have a new one but it did t happen. Did not detract from our stay. Beautiful views from restaurant. Good location. Taxis from the airport are expensive!! "
Charlotte 2-night trip
Posted 2 days ago
Grand Hotel Baglioni

More cheap stays in Castellina in Chianti

Hotel Bodoni

Hotel Bodoni

Via Martiri del Popolo, 27 Florence FI
The price is ฿2,342 per night from 7 Jan to 8 Jan
฿2,342
฿2,906 total
7 Jan - 8 Jan 2026
includes taxes & fees
8/10 Very Good! (776 reviews)

Frequently asked questions

Where is the best place to stay in Castellina in Chianti?
Belvedere di San Leonino is a favourite with Expedia customers. This hotel offers a winery and a restaurant. Other favourite options based on reviews include Hotel Colle Etrusco Salivolpi and Mariani Bed & Breakfast. See all available top hotels, or vacation rentals in Castellina in Chianti.
What are some of the best holiday rentals that Castellina in Chianti has to offer?
QK Costa58 Home Tower: This holiday 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. 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! The majority of hotel reservations are refundable if you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your check-in date. If you booked a non-refundable reservation, you might still have the option to cancel and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Castellina in Chianti.
What's the best family accommodation in 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. Borgo di Pietrafitta Relais is another good option for your child-friendly holiday. Also, attractions in the area such as Borgo di Vescine - Tenute di Castelvecchi and Siena Circuit are fun for children of all ages. Find more child-friendly accommodations in Castellina in Chianti.
What's the best dog-friendly place to stay in Castellina in Chianti?
Castello di Fonterutoli Wine Resort is a top B&B for people travelling 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.
What's the best luxury hotel 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 travellers looking for an elegant place to stay. Find more luxury hotels in Castellina in Chianti.
What are some accommodation options 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. The Social Hub Florence Lavagnini and Villa Neroli are a couple of other choices with an on-site pool. 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 on-site 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 is staying in Castellina in Chianti like?
Visitors to Castellina in Chianti will definitely enjoy the wineries. Tourists can also enjoy so much more including its forests. In Castellina in Chianti, there are 278 hotels and other accommodation options to choose from. Find out more about Castellina in Chianti.
What are the top places to visit in Castellina in Chianti?
Landmarks like Walls of Monteriggioni, Montecalvario and Castellina Fortress 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 itinerary are City Hall Castellina In Chianti and Casa Vinicola Luigi Cecchi. Take a look at what more there is to see and do in Expedia's Castellina in Chianti guide.
What's the seasonal weather like in Castellina in Chianti?
The hottest months are usually August and July, with an average temperature of 22°C, while the coldest months are January and February, with an average of 6°C. Average annual precipitation for Castellina in Chianti is 935 mm.