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Find hotels in Castiglione del Bosco from NT$2,409

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Dec 27 - Dec 28
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Dec 28 - Dec 29
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Our top choices for Castiglione del Bosco hotels

2 outdoor pools, open 8:30 AM to 6:30 PM, pool umbrellas, sun loungers
Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel
5.0 star property
Montalcino
10.0 out of 10, Exceptional, (70)
"Wonderful stay "
United States
Talib
The price is NT$42,528
NT$47,151 total
includes taxes & fees
Jan 4 - 2026/1/5
Castiglion del Bosco, A Rosewood Hotel
Exterior
Castello di Leonina Relais

Castello di Leonina Relais

Castello di Leonina Relais
4.0 star property
Asciano
9.0 out of 10, Wonderful, (120)
"Perfectb Quiet and very relaxing stay. Breakfast was very tasty and the view was absolutely spectacular "
United Kingdom
Mayara
The price is NT$4,375
NT$5,034 total
includes taxes & fees
Dec 28 - Dec 29
Castello di Leonina Relais
Garden
Palazzo Brandano

Palazzo Brandano

Palazzo Brandano
Trequanda
9.6 out of 10, Exceptional, (75)
"Excellent breakfast experience with farm fresh food with good service by staff. Spacious parking lot behind the property."
United States
KEVIN
The price is NT$3,031
NT$3,446 total
includes taxes & fees
Jan 4 - 2026/1/5
Palazzo Brandano
Restaurant
Palazzo Ravizza

Palazzo Ravizza

Palazzo Ravizza
4.0 star property
Siena Historical Center
9.4 out of 10, Exceptional, (750)
"We enjoyed our stay here."
United States
LAURIA
The price is NT$3,300
NT$3,741 total
includes taxes & fees
Jan 10 - 2026/1/11
Palazzo Ravizza
Terrace/patio
Hotel Athena

Hotel Athena

Hotel Athena
4.0 star property
Siena Historical Center
9.2 out of 10, Wonderful, (1000)
"Excellent hotel, very helpful staff, highly recommended "
United States
Vikram
The price is NT$2,593
NT$2,964 total
includes taxes & fees
Jan 27 - 2026/1/28
Hotel Athena
Ballroom
Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione
5.0 star property
Siena City Centre
9.2 out of 10, Wonderful, (576)
"Great hotel / room, city center, friendly staff. "
United States
Nebojsa
The price is NT$10,226
NT$11,471 total
includes taxes & fees
Jan 1 - 2026/1/2
Grand Hotel Continental Siena – Starhotels Collezione
Rooftop terrace
Villa del Sole Siena

Villa del Sole Siena

Villa del Sole Siena
Siena City Centre
9.8 out of 10, Exceptional, (627)
"Beautiful small hotel with an exceptional staff. "
United States
Raymond
The price is NT$4,666
NT$5,244 total
includes taxes & fees
Jan 22 - 2026/1/23
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, (1000)
"Great staff, wonderful breakfast, close to the plaza. "
United States
Izabela
The price is NT$2,089
NT$2,409 total
includes taxes & fees
Jan 11 - 2026/1/12
Hotel Italia
Front of property
Hotel Certosa Di Maggiano

Hotel Certosa Di Maggiano

Hotel Certosa Di Maggiano
4.0 star property
Siena
9.8 out of 10, Exceptional, (186)
"The best in Siena."
Canada
David
The price is NT$15,257
NT$16,894 total
includes taxes & fees
Dec 29 - Dec 30
Hotel Certosa Di Maggiano
Exterior
Locanda Vesuna

Locanda Vesuna

Locanda Vesuna
3.0 star property
Trequanda
9.4 out of 10, Exceptional, (52)
"Such a quiet and beautiful property, the hosts provided everything that was needed, and the location was great for visiting local Cantinas and Vineyards "
United States
Justin
The price is NT$2,634
NT$3,008 total
includes taxes & fees
Jan 12 - 2026/1/13
Locanda Vesuna
Porch
Relais degli Angeli

Relais degli Angeli

Relais degli Angeli
Siena City Centre
9.8 out of 10, Exceptional, (282)
"Very central and walkable. Wonderful staff and room was clean and comfortable. "
United States
Kristin
The price is NT$5,235
NT$5,906 total
includes taxes & fees
Dec 30 - Dec 31
Relais degli Angeli
Lobby
Hotel Chiusarelli

Hotel Chiusarelli

Hotel Chiusarelli
3.0 star property
Siena City Centre
8.8 out of 10, Excellent, (1000)
"The room was spotlessly clean, the staff were welcoming and helpful, and the breakfast was delicious!"
United States
Kenneth
The price is NT$2,848
NT$3,244 total
includes taxes & fees
Jan 12 - 2026/1/13
Hotel Chiusarelli
Front of property
Albergo Le Terme

Albergo Le Terme

Albergo Le Terme
4.0 star property
San Quirico d'Orcia
9.0 out of 10, Wonderful, (68)
"Very good hotel. The parking is a little bit far, good breakfast, i will recommend 👌 "
United States
liad
The price is NT$14,035
NT$15,623 total
includes taxes & fees
Jan 5 - 2026/1/6
Albergo Le Terme
Lunch and dinner served, local cuisine
La Posta Hotel & Thermal Spa

La Posta Hotel & Thermal Spa

La Posta Hotel & Thermal Spa
5.0 star property
San Quirico d'Orcia
9.6 out of 10, Exceptional, (70)
"Enjoyed our stay to the fullest!"
United States
Anna
The price is NT$17,339
NT$19,258 total
includes taxes & fees
Jan 6 - 2026/1/7
La Posta Hotel & Thermal Spa
Birthday party area
Siena Vip

Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (422)
"A great location!"
Canada
Cheryl
The price is NT$4,420
NT$5,010 total
includes taxes & fees
Jan 4 - 2026/1/5
Siena Vip
Bar (on property)
Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca
Siena City Centre
9.6 out of 10, Exceptional, (194)
"Great location and friendly staff. "
United States
Parissa
Il Battistero Siena - Residenza d'Epoca
Exterior
Capanna Suites

Capanna Suites

Capanna Suites
Montalcino
9.8 out of 10, Exceptional, (132)
"Absolutely amazing resort with amazing staff and service. Great food and beautiful spa experience. Highly reccommend anyone going to Tuscany to book here - you will not be disappointed ! "
Canada
Megan
Capanna Suites
Exterior
B&B Le Aquile

B&B Le Aquile

B&B Le Aquile
Siena City Centre
9.8 out of 10, Exceptional, (111)
"Staff was exceptionally helpful prior to arriving at property and offering suggestions for transportation to surrounding activities. Location was well situated to highlights and attractions. "
Canada
Lydia
B&B Le Aquile
Classic Double Room, Balcony, City View | Down comforters, in-room safe, desk, blackout drapes
Hotel Alma Domus

Hotel Alma Domus

Hotel Alma Domus
1.0 star property
Siena City Centre
8.8 out of 10, Excellent, (775)
"Great breakfast, clean rooms and wonderful area"
Canada
Treena
Hotel Alma Domus
32-inch Smart TV with digital channels, TV, streaming services
B&B Il Corso

B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (192)
"Safe, clean, close to all attractions"
Canada
Carlo
B&B Il Corso
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 Castiglione del Bosco attractions

Castiglion del Bosco Winery

You can enjoy a tasting or tour at Castiglion del Bosco Winery during your travels to Castiglione del Bosco.
See properties

Learn more about Castiglione del Bosco

Love history and dining out? Get away to Castiglione del Bosco!

See all hotels in Castiglione del Bosco
Beautiful view of the hotel pool (a number of the villas have their own pools) from a terrace above, with the Tuscan hillside in the background.
Photo by tom owens
Open Photo by tom owens

Top Castiglione del Bosco Hotel Reviews

Hotel Chiusarelli

Hotel Chiusarelli

10/10 Excellent
"The room was spotlessly clean, the staff were welcoming and helpful, and the breakfast was delicious!"
Kenneth 3-night trip
Posted 6 days ago
Hotel Chiusarelli

More cheap stays in Castiglione del Bosco

Piccolo Hotel Etruria

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI
The price is NT$2,624 per night from Dec 29 to Dec 30
NT$2,624
NT$2,997 total
Dec 29 - Dec 30
includes taxes & fees
7.8/10 Good! (389 reviews)

Frequently asked questions

What's the best place to stay in Castiglione del Bosco?
Castiglion del Bosco, A Rosewood Hotel is one of the top choices for your stay based on our traveler data. This hotel offers a winery and 2 outdoor pools. Two other options for your stay in the area are Hotel Athena and Borgo Grondaie. See all available top hotels, or vacation rentals in Castiglione del Bosco.
If I need to cancel my hotel reservation in Castiglione del Bosco, will I receive a refund?
Yes, you'll find most hotel bookings are refundable if you cancel before the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of check in. If you booked a non-refundable reservation, it might still be possible to cancel it and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Castiglione del Bosco.
Where can I learn more about changing or cancelling my trip to Castiglione del Bosco?
For additional details about changing or cancelling your trip to Castiglione del Bosco, go to https://www.expedia.com/service/.
What's the best boutique-style accommodation in Castiglione del Bosco?
Castiglion del Bosco, A Rosewood Hotel is a favorite hotel with our travelers looking for a stylish accommodation, and features 42 guestrooms, a winery, and 2 restaurants. See all boutique hotels in Castiglione del Bosco.
What's the best place to stay 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 Castiglione del Bosco like?
Visitors can enjoy all that Castiglione del Bosco has to offer including its restaurants. Tourists to the city can also enjoy its welcoming locals. There are 3218 hotels and other accommodations in the surrounding area. Find out more about Castiglione del Bosco.
What is there to see in Castiglione del Bosco?
A favorite place to visit is Castiglion del Bosco Winery. You'll also find Fortress of Montalcino and Castello di Montepescini in the area. Check out what more to see and do in Expedia's Castiglione del Bosco guide.
What's the weather like in Castiglione del Bosco?
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.

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