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Find hotels in Castiglione del Bosco from NT$2,406

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Dec 23 - Dec 24
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Dec 24 - Dec 25
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Dec 26 - Dec 28
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Our top choices for Castiglione del Bosco hotels

Villa (Agresto) | Living area | LCD TV, pay movies
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$42,595
NT$47,226 total
includes taxes & fees
Jan 4 - 2026/1/5
Castiglion del Bosco, A Rosewood Hotel
Terrace/patio
Hotel Athena

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 NT$2,775
NT$3,164 total
includes taxes & fees
Jan 15 - 2026/1/16
Hotel Athena
Interior
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$2,852
NT$3,249 total
includes taxes & fees
Jan 9 - 2026/1/10
Hotel Chiusarelli
Hiking
Borgo Sant'Ambrogio Resort

Borgo Sant'Ambrogio Resort

Borgo Sant'Ambrogio Resort
5.0 star property
Trequanda
9.8 out of 10, Exceptional, (98)
"It was very clean, excellent service and communication with every staff member was great, location was incredible, and overall a very pleasant stay. If you have the opportunity, the stay is great!"
United States
Juan Carlos
The price is NT$5,688
NT$6,367 total
includes taxes & fees
Jan 5 - 2026/1/6
Borgo Sant'Ambrogio Resort
Private spa tub
Grand Hotel Impero - Wellness & Exclusive SPA

Grand Hotel Impero - Wellness & Exclusive SPA

Grand Hotel Impero - Wellness & Exclusive SPA
4.0 star property
Castel del Piano
9.2 out of 10, Wonderful, (82)
"One of my favourite hotels. I make it a special trip to stay there."
Canada
Andre
The price is NT$2,628
NT$3,039 total
includes taxes & fees
Jan 19 - 2026/1/20
Grand Hotel Impero - Wellness & Exclusive SPA
Indoor pool, open 9:00 AM to midnight, sun loungers
Albergo San Biagio

Albergo San Biagio

Albergo San Biagio
3.0 star property
Montepulciano
8.6 out of 10, Excellent, (201)
"Great place to stay"
Canada
Robert
The price is NT$20,158
NT$22,322 total
includes taxes & fees
Dec 31 - 2026/1/1
Albergo San Biagio
Sundeck
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
Breakfast meal
Palazzo Ravizza

Palazzo Ravizza

Palazzo Ravizza
4.0 star property
Siena Historical Center
9.4 out of 10, Exceptional, (749)
"We enjoyed our stay here."
United States
LAURIA
The price is NT$3,309
NT$3,752 total
includes taxes & fees
Jan 6 - 2026/1/7
Palazzo Ravizza
Front of property
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$2,086
NT$2,406 total
includes taxes & fees
Jan 20 - 2026/1/21
Hotel Italia
Garden
Palace Hotel Due Ponti

Palace Hotel Due Ponti

Palace Hotel Due Ponti
3.0 star property
Due Ponti
8.2 out of 10, Very Good, (51)
"Nice place to stay. Fairly close to the medieval area. No need to worry about any ZTL issue. "
United States
joseph
Palace Hotel Due Ponti
Room amenity
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$4,409
NT$4,997 total
includes taxes & fees
Jan 4 - 2026/1/5
Siena Vip
Breakfast meal
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
Exterior
Borgo Grondaie

Borgo Grondaie

Borgo Grondaie
3.0 star property
Siena
9.6 out of 10, Exceptional, (440)
"A hidden gem overlooking the city set in stunning grounds"
United Kingdom
Philip
Borgo Grondaie
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
Seasonal outdoor pool, open 9:00 AM to 7:00 PM, sun loungers
Hotel Relais II Chiostro di Pienza

Hotel Relais II Chiostro di Pienza

Hotel Relais II Chiostro di Pienza
4.0 star property
Pienza
8.8 out of 10, Excellent, (630)
"Excellent location in the heart of pienza old town, the view to the Toscana hills and valleys was unique, great experience staying in this hotel "
United States
Pedro
Hotel Relais II Chiostro di Pienza
Lounge
Four Points by Sheraton Siena

Four Points by Sheraton Siena

Four Points by Sheraton Siena
4.0 star property
Scacciapensieri
8.8 out of 10, Excellent, (579)
"Comfortable rooms, excellent breakfast, lovely pool, and service!"
United States
Anonymous traveler
The price is NT$4,203
NT$4,734 total
includes taxes & fees
Dec 25 - Dec 26
Four Points by Sheraton Siena
Standard Double Room, City View | Egyptian cotton sheets, premium bedding, minibar, in-room safe
Hotel Minerva

Hotel Minerva

Hotel Minerva
3.0 star property
Siena City Centre
8.2 out of 10, Very Good, (1000)
"Helpful staff and overall vibe. "
United States
Robert
The price is NT$2,691
NT$3,071 total
includes taxes & fees
Jan 23 - 2026/1/24
Hotel Minerva
View from property
Vento Dorcia

Vento Dorcia

Vento Dorcia
Pienza
10.0 out of 10, Exceptional, (23)
"amazing place and people!"
United States
jorge
The price is NT$5,229
NT$5,900 total
includes taxes & fees
Jan 7 - 2026/1/8
Vento Dorcia
View from property
Agriturismo Il Macchione

Agriturismo Il Macchione

Agriturismo Il Macchione
Pienza
9.6 out of 10, Exceptional, (56)
"The owners and staff are hospitable .and accommodating very warm people "
Canada
aileen
Agriturismo Il Macchione
Balcony view
Hotel La Terrazza di Montepulciano

Hotel La Terrazza di Montepulciano

Hotel La Terrazza di Montepulciano
2.0 star property
Montepulciano
9.2 out of 10, Wonderful, (200)
"Great family owned hotel in the centre of the town "
United Kingdom
Jonathan
The price is NT$3,696
NT$4,213 total
includes taxes & fees
Jan 23 - 2026/1/24
Hotel La Terrazza di Montepulciano
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 2 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$2,580 per night from Dec 26 to Dec 27
NT$2,580
NT$2,949 total
Dec 26 - Dec 27
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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