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21 Dec - 22 Dec
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22 Dec - 23 Dec
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26 Dec - 28 Dec
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2 Jan - 4 Jan

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Our top choices for Castiglion del Bosco Winery 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
0.5 km from Castiglion del Bosco Winery
10.0 out of 10, Exceptional, (70)
"Wonderful stay "
United States
Talib
The price is AED 4,937
AED 5,474 total
includes taxes & fees
4 Jan - 5 January 2026
Castiglion del Bosco, A Rosewood Hotel
Spa
Mastrojanni Relais

Mastrojanni Relais

Mastrojanni Relais
13 km from Castiglion del Bosco Winery
10.0 out of 10, Exceptional, (61)
"This is the most magical and beautiful property in Tuscany with amazing food and service. The guests talk about how they come back every year to this resort The views from the pool are the best in this area. "
United States
Laura
The price is AED 1,545
AED 1,743 total
includes taxes & fees
24 Dec - 25 Dec
Mastrojanni Relais
Villa, Valley View | Garden view
Drogheria & Locanda Franci

Drogheria & Locanda Franci

Drogheria & Locanda Franci
6.5 km from Castiglion del Bosco Winery
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
6 Jan - 7 January 2026
Drogheria & Locanda Franci
Exterior
Capanna Suites

Capanna Suites

Capanna Suites
6.8 km from Castiglion del Bosco Winery
9.8 out of 10, Exceptional, (131)
"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
Deluxe Condo | Private kitchen | Full-size fridge, microwave, stovetop, dishwasher
Corte Francigena

Corte Francigena

Corte Francigena
12.7 km from Castiglion del Bosco Winery
9.8 out of 10, Exceptional, (6)
"Loved everything about my stay"
United States
Svetlana
The price is AED 600
AED 712 total
includes taxes & fees
4 Jan - 5 January 2026
Corte Francigena
Free daily buffet breakfast
L'Orto delle Terme

L'Orto delle Terme

L'Orto delle Terme
17.4 km from Castiglion del Bosco Winery
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
Terrace/patio
Locanda nel Cassero

Locanda nel Cassero

Locanda nel Cassero
14.6 km from Castiglion del Bosco Winery
9.6 out of 10, Exceptional, (5)
"Locanda confortevole e accogliente gentilezza e grande disponibilità "
Italy
Edoardo
The price is AED 334
AED 368 total
includes taxes & fees
29 Dec - 30 Dec
Locanda nel Cassero
Interior entrance
Hotel Osteria Dell Orcia

Hotel Osteria Dell Orcia

Hotel Osteria Dell Orcia
4.0 star property
17.9 km from Castiglion del Bosco Winery
9.6 out of 10, Exceptional, (46)
"Beautiful place in the Tuscan countryside. Excellent food and service. We had a lovely 2 night stay."
Denmark
Nick
Hotel Osteria Dell Orcia
Front of property
Idolina Guest House

Idolina Guest House

Idolina Guest House
6.4 km from Castiglion del Bosco Winery
9.4 out of 10, Exceptional, (105)
"The room met our expectations. Fulvia welcomed us and provided all info we needed. She was lovely and the room spacious and cosy. The location was perfect for our needs and we were very pleased."
United Kingdom
Kathrin
Idolina Guest House
Standard Double Room (La Piazza) | Desk, soundproofing, free WiFi, bed sheets
B&B Le Scalette di Piazza

B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
6.5 km from Castiglion del Bosco Winery
9.4 out of 10, Exceptional, (90)
"Great location and excellent staff. "
Canada
Jacek
B&B Le Scalette di Piazza
Breakfast, lunch, dinner served; Italian cuisine, garden views
Podere Spedalone

Podere Spedalone

Podere Spedalone
1.0 star property
18.8 km from Castiglion del Bosco Winery
9.4 out of 10, Exceptional, (42)
"Amazing food, amazing views"
United States
Juan
Podere Spedalone
Superior Apartment, 1 Bedroom, Ground Floor | 1 bedroom, minibar, individually decorated, desk
Agriturismo La casella

Agriturismo La casella

Agriturismo La casella
3.0 star property
7 km from Castiglion del Bosco Winery
9.0 out of 10, Wonderful, (30)
"It is a piece of heaven amazing location and views "
United States
Mariel
Agriturismo La casella
View from property
Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery
5.0 star property
14.1 km from Castiglion del Bosco Winery
9.0 out of 10, Wonderful, (340)
"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
Bar (on property)
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso

Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso

Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
15.4 km from Castiglion del Bosco Winery
9.0 out of 10, Wonderful, (46)
"Our stay was great. "
United States
Elena
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
Front of property
Albergo Le Terme

Albergo Le Terme

Albergo Le Terme
4.0 star property
17.4 km from Castiglion del Bosco Winery
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 AED 1,553
AED 1,729 total
includes taxes & fees
27 Dec - 28 Dec
Albergo Le Terme
Indoor pool, seasonal outdoor pool
Mercure Petriolo Siena Terme Spa Hotel

Mercure Petriolo Siena Terme Spa Hotel

Mercure Petriolo Siena Terme Spa Hotel
5.0 star property
9.7 km from Castiglion del Bosco Winery
8.8 out of 10, Excellent, (235)
"We had a great time. I would recommend this hotel when in Tuscany. "
United States
Mike
The price is AED 301
AED 331 total
includes taxes & fees
9 Jan - 10 January 2026
Mercure Petriolo Siena Terme Spa Hotel
Garden view
Hotel More Di Cuna

Hotel More Di Cuna

Hotel More Di Cuna
3.0 star property
18.3 km from Castiglion del Bosco Winery
8.8 out of 10, Excellent, (22)
"Nice place with excellent breakfast "
Australia
Vanessa
The price is AED 282
AED 323 total
includes taxes & fees
22 Dec - 23 Dec
Hotel More Di Cuna
Classic Double Room | Living area | 25-inch flat-screen TV with satellite channels, TV
Tuscany View, Montalcino

Tuscany View, Montalcino

Tuscany View, Montalcino
6.5 km from Castiglion del Bosco Winery
8.6 out of 10, Excellent, (8)
"Very nice place right in town convenient to everything"
United States
Bonnie
The price is AED 448
AED 528 total
includes taxes & fees
22 Dec - 23 Dec
Tuscany View, Montalcino
Seasonal outdoor pool, open 9:00 AM to 7:30 PM, pool umbrellas
Cordella in Montalcino Wine Resort

Cordella in Montalcino Wine Resort

Cordella in Montalcino Wine Resort
11.2 km from Castiglion del Bosco Winery
8.4 out of 10, Very Good, (21)
"One of the best places we stayed for one night , the host (owner and chef) was very friendly and the food he cooked was amazing - one of the best meals we had in the 3 weeks we stayed in Italy. Getting there by car was convenient but no easy to find. Once you are there the place is amazing and the food just great!"
Canada
Edgardo
The price is AED 369
AED 424 total
includes taxes & fees
22 Dec - 23 Dec
Cordella in Montalcino Wine Resort
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
13.1 km from Castiglion del Bosco Winery
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
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 Castiglion del Bosco Winery Hotel Reviews

Villa Le Prata - Residenza del Vescovo

Villa Le Prata - Residenza del Vescovo

10/10 Excellent
"We had a lovely stay here. It's a short drive from town and a beautiful property. We did a wine tasting of the delicious estate wines and a cooking class as well. The room is spacious, comfortable, and well decorated. The staff is really attentive and took great care of us, giving us advice on where to go, helping us get the car to town and make reservations, etc. We used the hot tub which was fantastic. Thanks for a great relaxing stay!"
Marysa 3-night trip
Posted 12 days ago
Villa Le Prata - Residenza del Vescovo

Hotels near other Castiglion del Bosco Winery attractions

Corte Pavone Winery

You can enjoy a tasting or tour at Corte Pavone Winery during your travels to Montalcino. Visit the area's spas, or simply enjoy its wineries.
See properties

Capanna of Cencioni

5.0/5 (1 review)
You can enjoy a tasting or tour at Capanna of Cencioni during your travels to Montalcino. Discover the area's countryside and wineries.
See properties

Frequently asked questions

What's the area like around Castiglion del Bosco Winery?
Castiglion del Bosco Winery is located in Castiglione del Bosco. You'll find 149 hotels and other accommodations within a few miles for a convenient home base.
What's the best hotel to stay near Castiglion del Bosco Winery?
Castiglion del Bosco, A Rosewood Hotel is one of the top choices for your stay based on our traveler data, and this hotel offers a winery and 2 outdoor pools. It's located just a short 0.3 mi (0.5 km) from Castiglion del Bosco Winery. Other good options within a few miles include Hotel Dei Capitani and Casali di Bibbiano.
How many hotels can I expect to find close to Castiglion del Bosco Winery?
Expedia has 149 hotels and other accommodations a few miles from Castiglion del Bosco Winery.
If I need to cancel the hotel reservation for my stay near Castiglion del Bosco Winery, will I receive a refund?
Yes! You'll find that most room reservations are fully refundable if you cancel before the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of your scheduled arrival. If you have a reservation that's non-refundable, you might still have the option to cancel and receive a refund within a 24-hour period of your booking. Enter your dates, click on "Search", then use the filter option "fully refundable" to get top deals close to Castiglion del Bosco Winery.
Where can I learn more about changing or cancelling my trip in the area near Castiglion del Bosco Winery?
To find more details about rescheduling or cancelling your stay near Castiglion del Bosco Winery, head over to our customer service page.
What can I see and do near Castiglion del Bosco Winery?
Sights like Fortress of Montalcino and Castello di Montepescini highlight some of the local culture. If you have some time to wander around the area, you might stop by Tenuta Greppo Franco Biondi Santi, Capanna of Cencioni, or Corte Pavone Winery. If you want to see more of the surrounding area, you can plan a visit to Civic and Diocesan Museum of Sacred Art of Montalcino and Cantina di Montalcino.

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