A poolside area with lounge chairs and umbrellas, surrounded by a forested landscape.

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Check prices for these dates

Tonight
21 Oct - 22 Oct
Tomorrow
22 Oct - 23 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

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Our top choices for Castiglione del Bosco hotels

An infinity pool with lounge chairs and umbrellas, surrounded by a forested hillside.
An open archway leading to a kitchen with a wooden ceiling, a hanging lantern, and a tiled backsplash.
An outdoor dining area with tables and chairs, large windows, and a view of the surrounding landscape.
A stone-walled room with a large arched doorway, a sofa, a table with a vase, and a view of the landscape.

1. Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel
Montalcino
United States
Mohammed
Rp22.347.171
Rp24.783.950 total
includes taxes & fees
3 Nov - 4 Nov
Castiglion del Bosco, A Rosewood Hotel
A person relaxing in a hot tub with a view of a vineyard and mountains in the background.
A stone building with a garden and a gazebo.
A pathway flanked by tall, narrow trees leading to a stone building with an arched entrance.
A picnic setup with blankets and cushions on a gravel surface, surrounded by cypress trees and a sunset in the background.

2. Villa Le Prata - Residenza del Vescovo

Villa Le Prata - Residenza del Vescovo
Montalcino
Canada
Karen
Rp7.855.521
Rp8.843.094 total
includes taxes & fees
4 Nov - 5 Nov
Villa Le Prata - Residenza del Vescovo
A stone building with a tiled roof, a paved pathway, and a well-maintained garden.
A stone building with a wooden deck and white lounge chairs.
A room with a wooden ceiling, a dining table with chairs, a bed, and a window with curtains.
A dining area with white tables and chairs, a large mirror, and a wine bottle on one table.

3. Podere Brizio

Podere Brizio
Montalcino
United States
Aseem
Rp3.603.249
Rp4.125.271 total
includes taxes & fees
16 Nov - 17 Nov
Podere Brizio
A poolside area with lounge chairs, a table with drinks, and a view of hills.
An open door leading to a patio with a view of the countryside, a table with plants, and a television on a wooden cabinet.
A room with a large window, a door, and a view of a landscape.
A four-poster bed with a bench, stone flooring, and a stone wall.

4. Capanna Suites

Capanna Suites
Montalcino
United States
Randy
Rp5.840.026
Rp6.626.090 total
includes taxes & fees
21 Nov - 22 Nov
Capanna Suites
A table with a glass of white wine, a metal pitcher, and a wooden board with various cheeses and cured meats.
A poolside area with lounge chairs, a table with wine glasses and a bottle, and a view of a mountainous landscape.
A kitchen with a buffet setup, including a variety of food items and glassware.
A hotel room with a bed, a sofa, a table with a vase of flowers, a TV, and a window with a view.

5. SI Montalcino Hotel

SI Montalcino Hotel
Montalcino
United States
Farasley
Rp1.707.740
Rp2.343.162 total
includes taxes & fees
3 Nov - 4 Nov
SI Montalcino Hotel
A hot tub with a view of a historic building and mountains.
A brick-walled bar with wooden shelves stocked with bottles, tables, and chairs.
A bedroom with a large window overlooking a castle, a bed, and a mirror on the wall.
A wine cellar with wooden racks and tables, a sign reading "DROGHERIA," and a rustic ceiling.

6. Casa Franci Montalcino

Casa Franci Montalcino
Montalcino
United States
Jim
Rp3.785.107
Rp4.365.639 total
includes taxes & fees
16 Nov - 17 Nov
Casa Franci Montalcino
A restaurant with tables and wicker chairs, large windows, and a view of buildings and greenery.
A balcony with a wrought iron railing overlooking a village with terracotta rooftops and greenery.
A courtyard with outdoor seating, a building with multiple windows, and a stone wall.
A multi-story building with a central entrance, large windows with shutters, and a paved courtyard.

7. Palazzo Saloni

Palazzo Saloni
Montalcino
United States
Michael
Rp4.703.412
Rp5.376.166 total
includes taxes & fees
2 Nov - 3 Nov
Palazzo Saloni
A pool with a modern water feature and a stone structure.
A buffet table with various desserts and a long dining area with tables and chairs.
A wicker dining table set with breakfast items, a vase of flowers, and a scenic view.
A large, multi-story building with a swimming pool, surrounded by lush greenery.

8. Mercure Petriolo Siena Terme Spa Hotel

Mercure Petriolo Siena Terme Spa Hotel
Civitella Paganico
Canada
Penny
Rp1.515.158
Rp1.707.078 total
includes taxes & fees
22 Oct - 23 Oct
Mercure Petriolo Siena Terme Spa Hotel
A stone building with a stone staircase, surrounded by lush greenery and a stone pathway.
A bedroom with a large bed, wooden beams on the ceiling, a nightstand with a lamp, and framed pictures on the wall.
A stone building with a swimming pool, white lounge chairs, and a white umbrella.
An outdoor patio with stone walls, green cushioned seating, a table with chairs, and a decorative umbrella.

9. Le Ragnaie

Le Ragnaie
Montalcino
United States
Trevor
Rp1.786.086
Rp2.167.027 total
includes taxes & fees
28 Oct - 29 Oct
Le Ragnaie
A logo with a bird and a shield, and the text "AMARAVATI".
A room with red leather sofas, a glass coffee table, and potted plants.
A breakfast table with croissants, a pitcher, a teapot, and a vase with flowers.
A hotel room with a large bed, a tray with tea and a teapot, and a decorative headboard.

10. Hotel Ghibellino

Hotel Ghibellino
Buonconvento
Australia
Anna-Maree
Rp1.657.381
Rp1.883.645 total
includes taxes & fees
28 Oct - 29 Oct
Hotel Ghibellino
A room with a view of a vineyard, a table with cups and saucers, and a window with curtains.
A modern kitchen with white cabinetry, a wooden dining table, and a vase with flowers.
A vineyard with terraced fields and a stone building with a sloped roof.
A bedroom with a bed, a nightstand, a lamp, and a window with a view of a vineyard and trees.

11. Wine Estate Paradiso di Cacuci

Wine Estate Paradiso di Cacuci
Montalcino
Italy
Tony
Rp4.933.225
Rp5.588.413 total
includes taxes & fees
22 Oct - 23 Oct
Wine Estate Paradiso di Cacuci
A pool with a stone wall, a view of the countryside, and a building with a tiled roof.
A buffet setup with various food items, a coffee station, and a counter with beverages.
A terrace with outdoor seating, a view of the landscape, and a building with large windows.
A spacious lobby with a tiled floor, a wooden reception desk, a staircase, and a large floral painting on the wall.

12. Hotel Dei Capitani

Hotel Dei Capitani
Montalcino
United States
Phillip
Rp2.413.234
Rp2.816.174 total
includes taxes & fees
28 Oct - 29 Oct
Hotel Dei Capitani
A spa area with a stone wall, wooden beams, a large window with a view, and a hot tub.
A landscaped garden with neatly trimmed bushes, a stone pathway, and umbrellas.
A picnic setup with a basket, blanket, pillows, and food items on a grassy area with a hilly landscape in the background.
A pool surrounded by manicured gardens and vineyards, with a clear view of rolling hills in the background.

13. Mastrojanni Relais - Small Luxury Hotels of the World

Mastrojanni Relais - Small Luxury Hotels of the World
Montalcino
United States
Gurnek
Rp7.964.407
Rp8.962.869 total
includes taxes & fees
7 Nov - 8 Nov
Mastrojanni Relais - Small Luxury Hotels of the World
A stone wall with a view of rolling hills and mountains.
A courtyard with stone buildings, potted plants, and outdoor seating.
A large stone castle with multiple towers, surrounded by vineyards and cypress trees.
An outdoor dining area with tables and chairs, a flower arrangement, and a view of the countryside.

14. Castello Banfi - Il Borgo - Relais et Chateaux

Castello Banfi - Il Borgo - Relais et Chateaux
Montalcino
United States
Jason
Rp20.018.455
Rp22.222.322 total
includes taxes & fees
31 Oct - 1 Nov
Castello Banfi - Il Borgo - Relais et Chateaux
A stone building with a pool overlooking a mountainous landscape.
A stone pathway leading to a gate with tall cypress trees on either side, illuminated by soft lighting.
A terrace with stone walls, potted plants, and outdoor furniture overlooking a valley with a river and distant hills during sunset.
A dining area with a table and chairs, a vase with flowers, and a view of the countryside through an arched window.

15. Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery
Montalcino
United States
Melanie
Rp10.198.118
Rp11.419.951 total
includes taxes & fees
15 Nov - 16 Nov
Castello di Velona Resort Thermal SPA & Winery
A room with a bed, a chair, a view through an open window, and a white dresser with bottles and glasses.
A stone building with the name "Albergoggiardino" above the entrance. Inside, there is a chandelier, a clock, and a blue chair.
A hotel room with a bed, a nightstand with bottles, a chair, and a wardrobe.
A courtyard with a stone wall, a small pond, and a waterfall. There are trees and plants around, and a building in the background.

16. Albergo Giardino

Albergo Giardino
Montalcino
United Kingdom
Norma
Rp2.148.770
Rp2.525.264 total
includes taxes & fees
15 Nov - 16 Nov
Albergo Giardino
A person serving food at a table with various dishes and a wine rack in the background.
An outdoor courtyard with a fire pit, seating area, and a large tree providing shade.
A room with a central island, a painting on the wall, and a potted plant.
A bedroom with a large bed, a wardrobe, a chair, and a ceiling with exposed beams.

17. Palazzo Lucchini

Palazzo Lucchini
Montalcino
Rp7.126.395
Rp8.041.056 total
includes taxes & fees
24 Oct - 25 Oct
Palazzo Lucchini
A couple in a hot spring with a large rock formation in the background.
A person in a white robe standing in a bamboo garden.
A restaurant with a bar area, dining tables, and chairs, with a view of the outdoors.
A hotel with a large building, a pool, and a landscaped garden.

18. ADLER Thermae

ADLER Thermae
San Quirico d'Orcia
United Kingdom
Abdel
Rp13.227.828
Rp14.651.622 total
includes taxes & fees
8 Nov - 9 Nov
ADLER Thermae
A pool with a wooden deck and lounge chairs, surrounded by trees and hills in the background.
A rustic interior with a brick fireplace, wooden beams, and a bar area.
An aerial view of a property with a main building, a swimming pool, and surrounding green fields.
A window with a view of a green landscape, including trees and distant hills.

19. Fattoria Pieve a Salti

Fattoria Pieve a Salti
Montalcino
United States
Marko
Rp2.148.770
Rp2.444.455 total
includes taxes & fees
9 Nov - 10 Nov
Fattoria Pieve a Salti
A bedroom with a bed, a chair, a table, and a stone wall.
An underground wine cellar with wooden tables, wine bottles, and a piano.
An underground wine cellar with brick walls, wooden tables, and chairs.
An outdoor patio with stone walls, a pergola, and a table set for dining.

20. Dimora delle Muse

Dimora delle Muse
Montalcino
United States
Bradley N.
Rp3.166.773
Rp3.645.068 total
includes taxes & fees
2 Nov - 3 Nov
Dimora delle Muse
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Stay near popular Castiglione del Bosco attractions

Castiglion del Bosco Winery

9.6/10 (5 reviews)
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
A stone staircase leading to a stone building surrounded by hedges.
Photo by Mario Mürner

Top Castiglione del Bosco Hotel Reviews

Il Chiostro del Carmine

Il Chiostro del Carmine

8/10 Good
"Air conditioning was not working well. The bathroom was beautiful but the shower was cycling between very hot to very cold"
Maurice 3-night trip
Posted 4 hours ago
Il Chiostro del Carmine
Hotel Italia

Hotel Italia

10/10 Excellent
"We stayed at this basic but nice 3-star hotel just one night while visiting Siena. We had a room for 3 for my wife and I and our adult daughter. The hotel was easy walking distance from the train/bus station. It's kind of weird because you enter an indoor shopping area across the street from the station and then go up about 6 banks of escalators to get up the hillside. Then the hotel is just a block away. One of the AC units didn't work but friendly staff helped start the other one. All staff were very friendly and spoke English. Easy walk a few blocks into the old city. Wonderful breakfast!!! We were able to leave our bags for most of the day while we explored the city prior to leaving on the bus again. I would definitely stay again."
Kurt 1-night trip
Posted 13 hours ago
Hotel Italia
Villa Ermellina Siena, a Tribute Portfolio Hotel

Villa Ermellina Siena, a Tribute Portfolio Hotel

8/10 Good
"We were in one of the other wings so it wasn't in the main building. It was a rainy week and we had a wedding and there were no rooms in the main building to accommodate us. There is no overhead so you will get wet and there are a million stairs to get to that wing (you will need help if you have a ton of luggage as well). The hotel is far from city center too, you need to plan your cabs out accordingly."
Marcela 3-night trip
Posted 22 hours ago
Villa Ermellina Siena, a Tribute Portfolio Hotel
Hotel San Gregorio

Hotel San Gregorio

10/10 Excellent
"Get"
Taisa 1-night trip
Posted 5 days ago
Hotel San Gregorio
Piccolo Hotel Etruria

Piccolo Hotel Etruria

10/10 Excellent
"This is a clean and charming hotel very centrally located in Siena. The morning and afternoon staff were very helpful. We will definitely stay at the Piccolo Hotel Etruria on our next visit. We will also recommend it to friends."
Thomas 1-night trip
Posted 5 days ago
Piccolo Hotel Etruria
L'Orto delle Terme

L'Orto delle Terme

10/10 Excellent
"Clean room and beautiful Suite. Breakfast was excellent!"
Tracey 2-night trip
Posted 6 days ago
L'Orto delle Terme
Hotel Chiusarelli

Hotel Chiusarelli

8/10 Good
"It was OK for the price. The breakfast was so so, the parking very small and often full. The building is old and was making weird noises occasionally. The location was excellent: just outside LTZ but very close to all the points of interest."
Victor 4-night trip
Posted 6 days ago
Hotel Chiusarelli
Four Points by Sheraton Siena

Four Points by Sheraton Siena

8/10 Good
"Property seem reasonable, staff helpful, rooms are little small and dated, bathrooms need renovation."
Rajendra 3-night trip
Posted 2 weeks ago
Four Points by Sheraton Siena
Albergo Le Terme

Albergo Le Terme

10/10 Excellent
"It was amazing."
PAUL 3-night trip
Posted 3 weeks ago
Albergo Le Terme

More cheap stays in Castiglione del Bosco

Cannon d'Oro

Cannon d'Oro

Via Montanini 28 Siena SI
Rp964.192
Rp1.121.217 total
21 Nov - 22 Nov
includes taxes & fees
7.8/10 Good! (259 reviews)
Cannon d'Oro
Piccolo Hotel Etruria

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI
Rp1.368.601
Rp1.566.067 total
6 Nov - 7 Nov
includes taxes & fees
7.8/10 Good! (453 reviews)
Piccolo Hotel Etruria
Albergo Centrale

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI
Rp1.561.991
Rp1.778.796 total
1 Nov - 2 Nov
includes taxes & fees
8.8/10 Excellent! (114 reviews)
Albergo Centrale
Torre del Fuggisole

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI
Rp1.585.792
Rp1.804.977 total
4 Nov - 5 Nov
includes taxes & fees
10/10 Exceptional! (52 reviews)
Torre del Fuggisole
Hotel La Terrazza di Montepulciano

Hotel La Terrazza di Montepulciano

Via Pié al Sasso 16 Montepulciano SI
Rp2.020.211
Rp2.303.041 total
22 Oct - 23 Oct
includes taxes & fees
9.4/10 Exceptional! (217 reviews)
Hotel La Terrazza di Montepulciano
Porta Pispini Residence

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI
Get ratesPorta Pispini Residence

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 traveller data. This hotel offers a winery and 2 outdoor pools. Other good options for your trip to the area are Hotel Athena and Grand Hotel Continental Siena – Starhotels Collezione. 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?
Castiglion del Bosco, A Rosewood Hotel 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 3395 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 Tenuta Greppo Franco Biondi Santi 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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