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Check prices for these dates

Next weekend
26 Dec - 28 Dec
In two weeks
2 Jan - 4 Jan
In one month
16 Jan - 18 Jan
In two months
13 Feb - 15 Feb

Our top choices for Castellina in Chianti bed & breakfast

Exterior
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)
"Amazing experience all around! Stayed for 2 nights!"
Canada
Matthew
The price is AED 718
AED 807 total
includes taxes & fees
22 Dec - 23 Dec
Castello di Fonterutoli Wine Resort
Aerial view
La Certosa di Pontignano

La Certosa di Pontignano

La Certosa di Pontignano
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (503)
"Excellent place to stay even for the next time. "
Canada
Xuejie
The price is AED 303
AED 350 total
includes taxes & fees
23 Dec - 24 Dec
La Certosa di Pontignano
Daily buffet breakfast (EUR 16 per person)
Florence Old Bridge

Florence Old Bridge

Florence Old Bridge
Historic Centre of Florence
8.2 out of 10, Very Good, (360)
"Loved our stay.. wonderful location "
United States
Jeff
Florence Old Bridge
Double Room, Garden View | Pillowtop beds, minibar, in-room safe, desk
La Fonderia Firenze

La Fonderia Firenze

La Fonderia Firenze
Oltrarno
9.6 out of 10, Exceptional, (172)
"Breakfast outside was lovely"
United States
Kenneth
The price is AED 375
AED 464 total
includes taxes & fees
22 Dec - 23 Dec
La Fonderia Firenze
Exterior detail
Il Chiostro del Carmine

Il Chiostro del Carmine

Il Chiostro del Carmine
Siena Historical Center
8.6 out of 10, Excellent, (870)
"Terrific place to stay. Breakfast was great, staff were friendly, and the view we had was stunning. Lots of room Old monastery was very interesting. "
Canada
John
Il Chiostro del Carmine
Down comforters, minibar, in-room safe, individually decorated
Quattro Cantoni

Quattro Cantoni

Quattro Cantoni
Siena City Centre
9.0 out of 10, Wonderful, (81)
"Absolutely loved this stay. The staff were incredibly helpful and got me taxis etc when I needed them. The room was so comfortable with high tech support for working and relaxing. The meals were absolutely delicious and served with great customer service. This was a gem of a place to stay. The area is also beautiful and has much to offer in terms of a relaxing stay. I would happily go again! "
United Kingdom
Yvonne
The price is AED 265
AED 309 total
includes taxes & fees
22 Dec - 23 Dec
Quattro Cantoni
Front of property
B&B San Francesco

B&B San Francesco

B&B San Francesco
Siena City Centre
9.4 out of 10, Exceptional, (46)
"Very nice enjoyable stay"
United States
Michael
B&B San Francesco
Interior
La Dimora Dei Monaci

La Dimora Dei Monaci

La Dimora Dei Monaci
Siena City Centre
10.0 out of 10, Exceptional, (86)
"Fantastic accommodations! Very comfortable bed! Spacious room, and beautiful. We definitely recommend."
United States
Karin
La Dimora Dei Monaci
Terrace/patio
Residenza d'Epoca Relais Campo Regio

Residenza d'Epoca Relais Campo Regio

Residenza d'Epoca Relais Campo Regio
Siena City Centre
9.8 out of 10, Exceptional, (90)
"It was the best cleanliness and quality of service, warmth and so beautiful pleasant stay!!! )))"
United States
elina
The price is AED 801
AED 899 total
includes taxes & fees
22 Dec - 23 Dec
Residenza d'Epoca Relais Campo Regio
Free daily buffet breakfast
A Casa di BiaGio B&B

A Casa di BiaGio B&B

A Casa di BiaGio B&B
Rapolano Terme
10.0 out of 10, Exceptional, (24)
"It is an increable place to stay. Unbealiable very charm and cozy decoration, with everything you need. "
United States
Juan Diego
The price is AED 422
AED 482 total
includes taxes & fees
11 Jan - 12 January 2026
A Casa di BiaGio B&B
Garden
Villa Fiorita

Villa Fiorita

Villa Fiorita
Camollia
8.2 out of 10, Very Good, (183)
"Easy parking in the street behind the building. Amazing hosts Very close to city center and yet find parking."
United Kingdom
Kushal
The price is AED 234
AED 275 total
includes taxes & fees
7 Jan - 8 January 2026
Villa Fiorita
Double Room | Desk, iron/ironing board, rollaway beds, free WiFi
Palazzo Mari

Palazzo Mari

Palazzo Mari
San Gimignano City Centre
9.8 out of 10, Exceptional, (77)
"Great location in a wonderful medieval town.. Just keep in mind that there are stairs and hills in this amazing destination."
Canada
Denis
Palazzo Mari
Food and drink
Villa Sestilia

Villa Sestilia

Villa Sestilia
Montaione
9.6 out of 10, Exceptional, (17)
"This is a lovely country property, perfect for relaxing and resting"
United States
Christian
The price is AED 525
AED 590 total
includes taxes & fees
22 Dec - 23 Dec
Villa Sestilia
In-room safe, desk, free WiFi, bed sheets
B&B Ponte a Nappo

B&B Ponte a Nappo

B&B Ponte a Nappo
San Gimignano
9.4 out of 10, Exceptional, (56)
"Beautiful private property with very comfortable suites with awesome views of San Gimignano and the breathtaking valley. Highly recommend, staff was very accommodating and friendly. "
United States
Mary
The price is AED 571
AED 650 total
includes taxes & fees
29 Dec - 30 Dec
B&B Ponte a Nappo
Double Room, Private Bathroom | Exterior
I Coppi

I Coppi

I Coppi
San Gimignano
9.8 out of 10, Exceptional, (70)
"What a wonderful place to stay in Tuscany the views alone form this B&B is amazing. The husband and wife are wonderful providing an excellent breakfast and overall stay. Buy the olive oil made on property!!!"
United States
Quenton
The price is AED 629
AED 714 total
includes taxes & fees
26 Dec - 27 Dec
I Coppi
Front of property
Country Lodge

Country Lodge

Country Lodge
Petriccio
8.6 out of 10, Excellent, (36)
"Very quiet and comfortable. The staff was so gracious and welcoming. "
United States
Annie
The price is AED 1,454
AED 1,617 total
includes taxes & fees
22 Dec - 23 Dec
Country Lodge
Free WiFi
L'Una Dimora

L'Una Dimora

L'Una Dimora
Certaldo
The price is AED 340
AED 383 total
includes taxes & fees
22 Dec - 23 Dec
L'Una Dimora
Double Room, Balcony | 1 bedroom, desk, blackout drapes, soundproofing
Il Sorriso

Il Sorriso

Il Sorriso
Oltrarno
9.2 out of 10, Wonderful, (129)
"Easy to check in remotely. It was located next to a lot of restaurants and a nice park that we were able to walk to. Angelica, the property manager was so helpful! She provided me with great information on how to check in and use keys to get into the building. "
United States
Natashka
Il Sorriso
Standard Double or Twin Room | Premium bedding, down comforters, memory foam beds, minibar
Atelier delle Grazie

Atelier delle Grazie

Atelier delle Grazie
Historic Centre of Florence
9.6 out of 10, Exceptional, (341)
"Great location! "
Canada
Susan
Atelier delle Grazie
Exterior
Le Stanze del Duomo

Le Stanze del Duomo

Le Stanze del Duomo
Historic Centre of Florence
8.8 out of 10, Excellent, (745)
"We were not offered breakfast. Also Santo Spiritu Room was nice, but our other family members got a lower quality room. "
United States
Patricia
The price is AED 1,664
AED 1,882 total
includes taxes & fees
30 Dec - 31 Dec
Le Stanze del Duomo
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 Calimala Florence

Hotel Calimala Florence

10/10 Excellent
"Room: We stayed in the family room. It’s small, but the decor is beautiful. You can hear street noise and drunk people at night. Didn’t bother me at all. Location: Great location. Easy to walk around. "
Jennifer 2-night trip
Posted 12 hours ago
Hotel Calimala Florence

Frequently asked questions

Searching for B&Bs in Castellina in Chianti?
Whether you're on a romantic trip and want to stay somewhere quiet and intimate, or you're traveling solo and hoping to make some connections, B&Bs can be a great choice for many types of vacationers. When you want to explore some attractions in town, City Hall Castellina In Chianti and Buondonno Winery are worth a stop.
Are you thinking about B&Bs over traditional hotel rooms?
With attentive service, opportunities to socialize with other guests, and hearty breakfasts, B&Bs offer a one-of-a-kind environment.
What are the top B&Bs in Castellina in Chianti?
Though there aren't any B&Bs in town, you might be interested in one of these choices if you're looking for an accommodation that offers free breakfast: Castello La LecciaLocanda le PiazzeHotel Casafrassi Wine ResortAgriturismo Villa Godenano - Pool & RestaurantAlbergo Il Colombaio
How many Bed & Breakfasts will I be able to find in Castellina in Chianti?
Expedia has 7 B&Bs for your time in Castellina in Chianti.
When is the best time to book my B&B in Castellina in Chianti?
When you're dreaming of a getaway to Castellina in Chianti, year-round temperatures and rainfall may be important factors to consider. 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.
What is there to do in Castellina in Chianti?
Travelers enjoy Castellina in Chianti for its countryside and wineries. If you're looking for some activities to entertain you on your trip, consider visiting Buondonno Winery and Casa Vinicola Luigi Cecchi. You might put City Hall Castellina In Chianti and Archaeological Museum of Chianti on your list if you want to see more of the area.
How can I get to and around Castellina in Chianti?
Planning your excursions in and around Castellina in Chianti is easier with these transportation options. Fly into Florence Airport, Peretola (FLR), which is located 23.2 mi (37.4 km) from the city center. If you'd like to venture out around the area, you may want a rental car for your journey.

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