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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 Castiglione del Bosco bed & breakfast

Porch
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
Interior
Antico Granaione

Antico Granaione

Antico Granaione
Rapolano Terme
9.8 out of 10, Exceptional, (59)
"old fashion building, clean and affordable"
United States
Irene
Antico Granaione
Lobby
Locanda del Loggiato

Locanda del Loggiato

Locanda del Loggiato
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (35)
"Location, nice staff, clean, beauty of this place: unique. "
Canada
Chucri
The price is AED 508
AED 576 total
includes taxes & fees
7 Jan - 8 January 2026
Locanda del Loggiato
Outdoor dining
Thalassa Locanda B&B e Appartamento

Thalassa Locanda B&B e Appartamento

Thalassa Locanda B&B e Appartamento
Arcidosso
9.6 out of 10, Exceptional, (16)
"Location "
Italy
raffaele
The price is AED 324
AED 369 total
includes taxes & fees
5 Jan - 6 January 2026
Thalassa Locanda B&B e Appartamento
Basic Double Room, Private Bathroom | 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
Daily buffet breakfast (EUR 7.50 per person)
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
Restaurant
Palazzo Nobile di San Donato

Palazzo Nobile di San Donato

Palazzo Nobile di San Donato
Montepulciano
9.4 out of 10, Exceptional, (70)
"The staff were very friendly. We enjoyed a lovely breakfast made to order and the hospitality was exceptional. "
United States
Jennifer
The price is AED 992
AED 1,109 total
includes taxes & fees
5 Jan - 6 January 2026
Palazzo Nobile di San Donato
Exterior detail
B&B Siena in Centro - Diffuso

B&B Siena in Centro - Diffuso

B&B Siena in Centro - Diffuso
Siena City Centre
8.6 out of 10, Excellent, (162)
"Great staff, good location and quiet"
United States
Molly
The price is AED 324
AED 373 total
includes taxes & fees
15 Jan - 16 January 2026
B&B Siena in Centro - Diffuso
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
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
Exterior
B&B da Nada Locanda Toscana

B&B da Nada Locanda Toscana

B&B da Nada Locanda Toscana
Roccastrada
9.4 out of 10, Exceptional, (15)
"Ras"
France
jean
The price is AED 231
AED 254 total
includes taxes & fees
7 Jan - 8 January 2026
B&B da Nada Locanda Toscana
Free daily buffet breakfast
L'Orto delle Terme

L'Orto delle Terme

L'Orto delle Terme
San Quirico d'Orcia
9.8 out of 10, Exceptional, (32)
"Amazing stay. Very happy with all aspects "
United States
John
The price is AED 814
AED 912 total
includes taxes & fees
21 Jan - 22 January 2026
L'Orto delle Terme
Exterior
Cordella in Valdorcia Truffle & Olive Oil Resort - Podere Borgasso

Cordella in Valdorcia Truffle & Olive Oil Resort - Podere Borgasso

Cordella in Valdorcia Truffle & Olive Oil Resort - Podere Borgasso
Montalcino
8.2 out of 10, Very Good, (10)
"Amazing view"
Italy
Ilaria
The price is AED 334
AED 385 total
includes taxes & fees
22 Dec - 23 Dec
Cordella in Valdorcia Truffle & Olive Oil Resort - Podere Borgasso
Dining
La Corte Medicea

La Corte Medicea

La Corte Medicea
Montepulciano
9.0 out of 10, Wonderful, (37)
"We loved our stay."
United States
Donna
La Corte Medicea
Royal Suite | Down comforters, desk, laptop workspace, soundproofing
Il Senesino

Il Senesino

Il Senesino
Siena City Centre
9.0 out of 10, Wonderful, (24)
"this is a very nice place. if I ever return to siena, I will stay here. the owners were lovely, and the location is superb, as is the coffee"
United States
thomas
The price is AED 374
AED 429 total
includes taxes & fees
18 Jan - 19 January 2026
Il Senesino
Villa, Valley View | Garden view
Drogheria & Locanda Franci

Drogheria & Locanda Franci

Drogheria & Locanda Franci
Montalcino
9.8 out of 10, Exceptional, (16)
"Would stay here again."
United States
Martin
The price is AED 886
AED 1,017 total
includes taxes & fees
22 Dec - 23 Dec
Drogheria & Locanda Franci
Terrace/patio
Alle Terme B&B

Alle Terme B&B

Alle Terme B&B
Rapolano Terme
8.4 out of 10, Very Good, (20)
"We found the facility, very clean and the manager was very understanding and nice. A very nice asdortment of foods for breakfast was available. Would highly recommend this charming accomodation. "
United States
Cheryl
Alle Terme B&B
55-inch Smart TV with satellite channels, TV, Netflix
Palazzo Carletti

Palazzo Carletti

Palazzo Carletti
Montepulciano
9.8 out of 10, Exceptional, (241)
"Excelente hotel."
Mexico
jorge
Palazzo Carletti
Free daily continental breakfast
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
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 Castiglione del Bosco Hotel Reviews

Palazzo Ravizza

Palazzo Ravizza

10/10 Excellent
"Having booked with another local hotel - The Athena - who were completely obnoxious and unhelpful regarding the parking. I stumbled across this gem. The staff were so helpful and accomplished ~ first class customer service."
Stephen 1-night trip
Posted 4 days ago
Palazzo Ravizza

Frequently asked questions

Searching for B&Bs in Castiglione del Bosco?
If you're looking for something a little quirkier than the traditional hotel experience, a stay at a bed and breakfast could be a great option for your vacation. When you want to explore some of the destination's attractions, Castiglion del Bosco Winery is worth a visit.
Are you thinking about a B&B for your stay?
B&Bs all have a unique charm. Whether it's a cozy reading space or a sunlit breakfast nook, the quaint details are what make bed and breakfasts the perfect escape.
What are the best B&Bs in Castiglione del Bosco?
Below are some well-liked B&Bs in the area: Drogheria & Locanda Franci: 11 rooms. 3.9 mi (6.4 km) from the heart of Castiglione del Bosco. Enjoy the free full breakfast and onsite dining. B&B San Francesco: 8 rooms. 17.1 mi (27.5 km) from the downtown core. Il Chiostro del Carmine: 21 rooms. Situated 16.6 mi (26.7 km) from the heart of Castiglione del Bosco. Enjoy the free buffet breakfast and in-room dining. Palazzo Nobile di San Donato: 4 rooms. 18.2 mi (29.2 km) from the heart of downtown. Enjoy the designer toiletries and onsite dining. B&B Pantaneto Palazzo Bulgarini: 6 rooms. Located 16.8 mi (27 km) from the core of Castiglione del Bosco.
When is the best time to book my B&B in Castiglione del Bosco?
When you're planning your escape to Castiglione del Bosco, 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 Castiglione del Bosco is 37 inches.
What is there to do in Castiglione del Bosco?
When you want to explore some things to do in Castiglione del Bosco, consider a visit to Castiglion del Bosco Winery. Fortress of Montalcino and Castello di Montepescini are also some sites to visit if you want to see more of the area.

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