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Find hotels in Castiglione del Bosco from ฿2,675

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4 Dec - 5 Dec
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5 Dec - 6 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

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Top 10 Castiglione del Bosco hotels and places to stay

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

Castiglion del Bosco, A Rosewood Hotel

5.0 star property
Montalcino
10.0 out of 10, Exceptional, (69)
"Definitely the best property in Tuscany.. People, food, amenities, the property itself - all perfect !"
United Kingdom
IOSEFIN
The price is ฿40,382
฿44,793 total
includes taxes & fees
3 Jan - 4 Jan 2026
Castiglion del Bosco, A Rosewood Hotel
Jetted bathtub
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, (81)
"One of my favourite hotels. I make it a special trip to stay there."
Canada
Andre
The price is ฿2,648
฿3,062 total
includes taxes & fees
16 Dec - 17 Dec
Grand Hotel Impero - Wellness & Exclusive SPA
Villa, Valley View | Garden view
Drogheria & Locanda Franci

Drogheria & Locanda Franci

Montalcino
9.8 out of 10, Exceptional, (16)
"Would stay here again."
United States
Martin
The price is ฿7,742
฿8,889 total
includes taxes & fees
18 Dec - 19 Dec
Drogheria & Locanda Franci
Garden
Borgo Sant'Ambrogio Resort

Borgo Sant'Ambrogio Resort

5.0 star property
Trequanda
9.8 out of 10, Exceptional, (97)
"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 ฿3,254
฿3,691 total
includes taxes & fees
5 Dec - 6 Dec
Borgo Sant'Ambrogio Resort
Restaurant
Palazzo Nobile di San Donato

Palazzo Nobile di San Donato

Montepulciano
9.4 out of 10, Exceptional, (67)
"Unique experience in a central location "
United States
Neil T
The price is ฿6,798
฿7,627 total
includes taxes & fees
9 Dec - 10 Dec
Palazzo Nobile di San Donato
Lunch and dinner served, local cuisine
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 ฿13,400
฿14,926 total
includes taxes & fees
16 Dec - 17 Dec
La Posta Hotel & Thermal Spa
Land view from property
Hotel Corsignano

Hotel Corsignano

4.0 star property
Pienza
9.4 out of 10, Exceptional, (329)
"Enjoyed the hotel. Great location, quality breakfast and rooms."
United States
Joseph
The price is ฿4,781
฿5,483 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hotel Corsignano
Seasonal outdoor pool, pool umbrellas, pool loungers
Villa Le Prata - Residenza del Vescovo

Villa Le Prata - Residenza del Vescovo

Montalcino
10.0 out of 10, Exceptional, (72)
"Incredible stay!"
Canada
Tomasz
Villa Le Prata - Residenza del Vescovo
Free daily continental breakfast
Hotel Relais II Chiostro di Pienza

Hotel Relais II Chiostro di Pienza

4.0 star property
Pienza
8.8 out of 10, Excellent, (629)
"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
View from property
Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

5.0 star property
Montalcino
9.0 out of 10, Wonderful, (339)
"The property was exquisite. The view spectacular and the staff top notch. The indoor and outdoor thermal pools and sauna made our stay very relaxing. The buffet breakfast was amazing."
United States
Jose
Castello di Velona Resort Thermal SPA & Winery
Free daily buffet breakfast
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
L'Orto delle Terme
Seasonal outdoor pool, open 9:30 AM to 7:30 PM, pool umbrellas
Le Ragnaie

Le Ragnaie

Montalcino
9.2 out of 10, Wonderful, (323)
"Great place to stay the staff was super friendly and very close to Monalcino. Good wine everywhere. The scenery was so beautiful! "
United States
Douglas
Le Ragnaie
Terrace/patio
Castello

Castello

3.0 star property
Sovicille
8.6 out of 10, Excellent, (70)
"Great little place to stay overnight. "
United States
Ivona
Castello
Front of property
Rossellino

Rossellino

Pienza
8.6 out of 10, Excellent, (55)
"Quaint hotel in the heart of Pienza. Comfortable and close to all amenities. "
Canada
Debbie
The price is ฿4,112
฿4,672 total
includes taxes & fees
9 Dec - 10 Dec
Rossellino
Front of property – evening/night
Relais Le Macine di Stigliano

Relais Le Macine di Stigliano

4.0 star property
Sovicille
10.0 out of 10, Exceptional, (15)
"Amazing staff. Beautiful views and facilities. Treated like friends. "
United States
Josh
The price is ฿5,118
฿5,816 total
includes taxes & fees
11 Dec - 12 Dec
Relais Le Macine di Stigliano
Seasonal outdoor pool, open 9:30 AM to 7:00 PM, pool loungers
Hotel Vecchia Oliviera

Hotel Vecchia Oliviera

3.0 star property
Montalcino
9.6 out of 10, Exceptional, (62)
"Beautiful hotel. Very kind and friendly staff. Comfortable and many amenities! The view from our room was amazing!"
United States
Jennifer
Hotel Vecchia Oliviera
Front of property
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 ฿12,660
฿14,112 total
includes taxes & fees
5 Dec - 6 Dec
Albergo Le Terme
Exterior
Capanna Suites

Capanna Suites

Montalcino
9.8 out of 10, Exceptional, (130)
"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
Locanda Vesuna

Locanda Vesuna

3.0 star property
Trequanda
9.4 out of 10, Exceptional, (50)
"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 ฿2,955
฿3,362 total
includes taxes & fees
5 Dec - 6 Dec
Locanda Vesuna
Seasonal outdoor pool, pool umbrellas, pool loungers
Hotel Palazzo del Capitano Wellness & Relais - Luxury Borgo Capitano Collection

Hotel Palazzo del Capitano Wellness & Relais - Luxury Borgo Capitano Collection

4.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (228)
"The property and the room was beautiful. The staff was so helpful!"
United States
Kyla
The price is ฿5,742
฿6,502 total
includes taxes & fees
5 Dec - 6 Dec
Hotel Palazzo del Capitano Wellness & Relais - Luxury Borgo Capitano Collection
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? 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

Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent
"The property was exquisite. The view spectacular and the staff top notch. The indoor and outdoor thermal pools and sauna made our stay very relaxing. The buffet breakfast was amazing."
Jose 3-night trip
Posted 3 weeks ago
Castello di Velona Resort Thermal SPA & Winery

More cheap stays in Castiglione del Bosco

Piccolo Hotel Etruria

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI
The price is ฿2,599 per night from 8 Dec to 9 Dec
฿2,599
฿2,971 total
8 Dec - 9 Dec
includes taxes & fees
7.8/10 Good! (388 reviews)

Frequently asked questions

What's the best place to stay in Castiglione del Bosco?
Rosewood Castiglion del Bosco is one of the top choices for your stay based on our traveller data. This hotel offers a winery and 2 outdoor pools. Other good options for your trip to the area are Hotel Athena and Palazzo Ravizza. 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! Most room reservations are fully refundable as long as you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your arrival date. If you have a reservation that's non-refundable, you might still have the option to cancel and get a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Castiglione del Bosco.
What's the best boutique-style hotel in Castiglione del Bosco?
Rosewood Castiglion del Bosco is a favourite hotel with our travellers looking for stylish accommodation, and features 42 guestrooms, a winery and 2 restaurants. See all boutique hotels in Castiglione del Bosco.
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 3253 hotels and other accommodation options in the surrounding area. Find out more about Castiglione del Bosco.
What should I do while I'm visiting Castiglione del Bosco?
A favourite place to visit is Castiglion del Bosco Winery. You'll also find Fortress of Montalcino and Castello di Montepescini in the area. Take a look at what more there is 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 temperature of 22°C, while the coldest months are January and February, with an average of 6°C. Average annual precipitation for Castiglione del Bosco is 944 mm.

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