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Find hotels in Castiglione del Bosco from 2.177.323 ₫

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15 Dec - 16 Dec
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16 Dec - 17 Dec
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19 Dec - 21 Dec
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26 Dec - 28 Dec

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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, pool 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, (69)
Nestled in Montalcino, this lavish hotel offers Italian dining at Campo del Drago restaurant, rejuvenating spa treatments, and an exclusive golf course. Enjoy the poolside bar and rooftop terrace while nearby wineries beckon exploration.
"Wonderful stay "
United States
Talib
The price is 31.914.301 ₫
35.414.695 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
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)
Lose yourself in the Italian countryside at this historic relais. Unwind with deep-tissue massages and Ayurvedic treatments after exploring nearby Siena. The outdoor pool, hot tub, and Italian cuisine at Il Balcone di Leonina complete your authentic escape.
"Perfectb Quiet and very relaxing stay. Breakfast was very tasty and the view was absolutely spectacular "
United Kingdom
Mayara
The price is 3.955.610 ₫
4.536.475 ₫ total
includes taxes & fees
27 Dec - 28 Dec
Castello di Leonina Relais
Garden
Palazzo Brandano

Palazzo Brandano

Palazzo Brandano
Trequanda
9.6 out of 10, Exceptional, (73)
Elegant retreat in Trequanda with daily housekeeping and free WiFi. Relax in the peaceful garden or on the terrace. Just minutes from cultural treasures like Monastery of Sant'Anna in Camprena and RI Crea RE.
"Excellent breakfast experience with farm fresh food with good service by staff. Spacious parking lot behind the property."
United States
KEVIN
The price is 1.693.005 ₫
1.954.957 ₫ total
includes taxes & fees
16 Dec - 17 Dec
Palazzo Brandano
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, (574)
Set in historic Siena, this hotel offers 2 elegant bars and authentic local cuisine at Sapordivino restaurant. Rooms combine luxury with old-world charm, and the attentive staff ensures a memorable stay near Banca Monte dei Paschi di Siena.
"Great hotel / room, city center, friendly staff. "
United States
Nebojsa
The price is 7.861.384 ₫
8.832.827 ₫ total
includes taxes & fees
13 Jan - 14 Jan 2026
Grand Hotel Continental Siena – Starhotels Collezione
Terrace/patio
Hotel Athena

Hotel Athena

Hotel Athena
4.0 star property
Siena Historical Center
9.2 out of 10, Wonderful, (1008)
This business-friendly hotel offers a scenic rooftop terrace, free WiFi, and complimentary parking. Guests praise the delicious breakfast and attentive staff. Sample local cuisine at Mangia restaurant, relax at the bar, or visit nearby National Museum of Archaeology.
"Excellent hotel, very helpful staff, highly recommended "
United States
Vikram
The price is 2.319.080 ₫
2.643.671 ₫ total
includes taxes & fees
8 Jan - 9 Jan 2026
Hotel Athena
Restaurant
Palazzo Ravizza

Palazzo Ravizza

Palazzo Ravizza
4.0 star property
Siena Historical Center
9.4 out of 10, Exceptional, (746)
Located near Pinacoteca Nazionale, this Siena hotel offers free WiFi, room service, and a tranquil terrace garden. Just minutes from the National Museum of Archaeology, guests rave about the delicious breakfast and attentive staff.
"We enjoyed our stay here."
United States
LAURIA
The price is 2.729.023 ₫
3.094.577 ₫ total
includes taxes & fees
16 Dec - 17 Dec
Palazzo Ravizza
Rooftop terrace
Villa del Sole Siena

Villa del Sole Siena

Villa del Sole Siena
Siena City Centre
9.8 out of 10, Exceptional, (627)
This business-friendly hotel offers free breakfast and WiFi near All'Orto de' Pecci and Piazza del Mercato. Enjoy drinks at the bar or snacks from the deli before relaxing in the garden. Guests consistently praise the exceptionally helpful staff.
"Beautiful small hotel with an exceptional staff. "
United States
Raymond
The price is 3.812.771 ₫
4.286.700 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Villa del Sole Siena
Exterior
Locanda Vesuna

Locanda Vesuna

Locanda Vesuna
3.0 star property
Trequanda
9.4 out of 10, Exceptional, (52)
Immerse yourself in the Tuscan countryside with views from the elevated terrace. This family-friendly retreat offers a refreshing seasonal pool, garden, and on-site café. Explore nearby Monastery of Sant'Anna in Camprena after a relaxing drink at the bar.
"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 2.349.993 ₫
2.677.644 ₫ total
includes taxes & fees
19 Dec - 20 Dec
Locanda Vesuna
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)
Experience Siena from this convenient hotel near the train station. Enjoy hiking and mountain biking trails nearby, plus visit Porta Camollia and Siena Stadium. Relax at the bar or on the terrace after exploring. Guests consistently praise the helpful staff and morning breakfast.
"Great staff, wonderful breakfast, close to the plaza. "
United States
Izabela
The price is 1.895.155 ₫
2.177.323 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Hotel Italia
Exterior
Capanna Suites

Capanna Suites

Capanna Suites
Montalcino
9.8 out of 10, Exceptional, (131)
Italian elegance meets vineyard charm at this countryside retreat with on-site winery. After savouring local wines at the poolside bar, indulge in Italian cuisine at Il Passaggio by Capanna restaurant before relaxing with rejuvenating spa treatments.
"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
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
Montalcino
9.0 out of 10, Wonderful, (340)
Immerse in Castello di Velona's sensory escape featuring 3 restaurants, multiple pools, and a rejuvenating thermal spa. Near Abbazia di Sant'Antimo and Museum of Brunello, this winery hotel offers complimentary breakfast, WiFi, and parking.
"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
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, (185)
Discover serene luxury adjacent to a golf course in Siena, where an outdoor pool and tennis courts await. After activities, enjoy the bar or café. Located near Porta Romana with free breakfast, WiFi, and parking.
"The best in Siena."
Canada
David
The price is 5.476.999 ₫
6.117.351 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Hotel Certosa Di Maggiano
Lobby
Hotel Chiusarelli

Hotel Chiusarelli

Hotel Chiusarelli
3.0 star property
Siena City Centre
8.8 out of 10, Excellent, (1000)
Charming hotel with a restaurant and garden terrace near Stadio Artemio Franchi. Enjoy the complimentary breakfast before exploring nearby Fontebranda. The attentive staff ensures a comfortable stay while room service and free WiFi add convenience.
"Lovely staff and great location with a quiet, comfortable room."
United States
Katherine
The price is 2.507.164 ₫
2.850.594 ₫ total
includes taxes & fees
9 Jan - 10 Jan 2026
Hotel Chiusarelli
Spa
Mastrojanni Relais

Mastrojanni Relais

Mastrojanni Relais
Montalcino
10.0 out of 10, Exceptional, (61)
Surrounded by Montalcino vineyards, this farm stay offers a seasonal outdoor pool and fitness centre. Dine at the on-site restaurant after exploring nearby Abbazia di Sant'Antimo. Free breakfast, WiFi and parking enhance your Tuscan countryside retreat.
"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 11.098.029 ₫
12.516.672 ₫ total
includes taxes & fees
19 Dec - 20 Dec
Mastrojanni Relais
Birthday party area
Siena Vip

Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (422)
Set adjacent to a golf course with easy access to Fontebranda and Piccolomini Library. This hotel offers refrigerators and microwaves in rooms, plus free WiFi and room service. Guests love the helpful staff and clean accommodation.
"A great location!"
Canada
Cheryl
Siena Vip
Exterior
B&B Le Aquile

B&B Le Aquile

B&B Le Aquile
Siena City Centre
9.8 out of 10, Exceptional, (111)
Just steps from iconic Piazza del Campo, this guesthouse combines prime location with comfort. Free WiFi and premium bedding enhance your stay while Museum of Torture and Palazzo Chigi-Saracini await nearby.
"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
Porch
Relais degli Angeli

Relais degli Angeli

Relais degli Angeli
Siena City Centre
9.8 out of 10, Exceptional, (281)
Set in the heart of Siena, this charming inn offers a rooftop terrace with city views. Hiking trails nearby provide outdoor adventure, while Palazzo Salimbeni and Piazza Salimbeni are just around the corner. Siena Station is an 18-minute walk away.
"Very central and walkable. Wonderful staff and room was clean and comfortable. "
United States
Kristin
The price is 3.418.784 ₫
3.884.198 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Relais degli Angeli
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)
Admire scenic vistas from the terrace of this San Quirico d'Orcia hotel. Rejuvenate with deep-tissue massages and aromatherapy at the spa, then unwind in the indoor pool and sauna. Near Piazza delle Sorgenti, with free breakfast and parking.
"Very good hotel. The parking is a little bit far, good breakfast, i will recommend 👌 "
United States
liad
The price is 11.412.060 ₫
12.707.686 ₫ total
includes taxes & fees
27 Dec - 28 Dec
Albergo Le Terme
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, (191)
Immersed in Siena's heart, this B&B offers premium bedding and free WiFi near Teatro dei Rozzi and Fonte Gaia. Daily housekeeping ensures comfort while you explore local attractions. Siena Station is just a 9-minute drive away.
"Safe, clean, close to all attractions"
Canada
Carlo
B&B Il Corso
Classic Double Room, Balcony, City View | Down duvets, in-room safe, desk, blackout curtains
Hotel Alma Domus

Hotel Alma Domus

Hotel Alma Domus
1.0 star property
Siena City Centre
8.8 out of 10, Excellent, (773)
Enjoy panoramic views of Siena from this central hotel where a complimentary buffet breakfast starts each morning. The 24-hour front desk staff receives high marks from guests, and the location near Fontebranda and Casa di Santa Caterina can't be beat.
"Great breakfast, clean rooms and wonderful area"
Canada
Treena
Hotel Alma Domus
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

More cheap stays in Castiglione del Bosco

Albergo Centrale

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI
The price is 1.933.059 ₫ per night from 16 Dec to 17 Dec
1.933.059 ₫
2.219.017 ₫ total
16 Dec - 17 Dec
includes taxes & fees
8.8/10 Excellent! (89 reviews)

Hotels in Castiglione del Bosco with star rating

Frequently asked questions

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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