𝗧𝗢𝗣 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Castiglione del Bosco from RM271 (2026) - Fully Refundable Options

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

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Our top choices for Castiglione del Bosco hotels

A stone-walled room with a large arched doorway, a sofa, a table with a vase, and a view of the landscape.

An outdoor dining area with tables and chairs, large windows, and a view of the surrounding landscape.

A villa with a swimming pool, surrounded by lush greenery and a view of distant hills.

An open archway leading to a kitchen with a wooden ceiling, a hanging lantern, and a tiled backsplash.

1. Castiglion del Bosco, A Rosewood Hotel

Montalcino

Mohammed

RM7,488

RM8,282 total

includes taxes & fees

30 Oct - 31 Oct

A table with a glass of white wine, a metal pitcher, and a wooden board with various cheeses and cured meats.

A hotel room with a bed, a sofa, a table with a vase of flowers, a TV, and a window with a view.

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.

2. SI Montalcino Hotel

Montalcino

Farasley

RM387

RM531 total

includes taxes & fees

1 Nov - 2 Nov

A stone building with a tiled roof, a paved pathway, and a well-maintained garden.

A dining area with white tables and chairs, a large mirror, and a wine bottle on one table.

A room with a wooden ceiling, a dining table with chairs, a bed, and a window with curtains.

A stone building with a wooden deck and white lounge chairs.

3. Podere Brizio

Montalcino

Aseem

RM816

RM934 total

includes taxes & fees

31 Oct - 1 Nov

A person relaxing in a hot tub with a view of a vineyard and mountains in the background.

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.

A dining area with a wooden table set for a meal, a fireplace, and a painting on the wall.

4. Villa Le Prata - Residenza del Vescovo

Montalcino

Karen

RM1,753

RM1,974 total

includes taxes & fees

5 Nov - 6 Nov

A bar area with two people seated at a counter, a glass display case with bottles, and a vase with flowers on the wall.

A hotel room with a large bed, a tray with tea and a teapot, and a decorative headboard.

A room with red leather sofas, a glass coffee table, and potted plants.

5. Hotel Ghibellino

Buonconvento

Anna-Maree

RM375

RM427 total

includes taxes & fees

18 Oct - 19 Oct

A pool with a stone wall, a view of the countryside, and a building with a tiled roof.

A spacious lobby with a tiled floor, a wooden reception desk, a staircase, and a large floral painting on the wall.

A terrace with outdoor seating, a view of the landscape, and a building with large windows.

A hotel with a classic facade, multiple windows with shutters, and a sign indicating it is the "Hotel dei Capitani."

6. Hotel Dei Capitani

Montalcino

Phillip

RM532

RM621 total

includes taxes & fees

20 Oct - 21 Oct

A poolside area with lounge chairs, a table with drinks, and a view of hills.

A villa with a swimming pool, stone buildings, and a view of the surrounding countryside.

A four-poster bed with a bench, stone flooring, and a stone wall.

An open door leading to a patio with a view of the countryside, a table with plants, and a television on a wooden cabinet.

7. Capanna Suites

Montalcino

Michael

RM1,323

RM1,501 total

includes taxes & fees

26 Oct - 27 Oct

A stone building with a stone staircase, surrounded by lush greenery and a stone pathway.

A spacious living area with leather armchairs, a wooden cabinet with glass doors, and a red carpet.

An outdoor patio with stone walls, green cushioned seating, a table with chairs, and a decorative umbrella.

A stone building with a swimming pool, white lounge chairs, and a white umbrella.

8. Le Ragnaie

Montalcino

Trevor

RM404

RM490 total

includes taxes & fees

3 Nov - 4 Nov

A hot tub with a view of a historic building and mountains.

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.

A brick-walled bar with wooden shelves stocked with bottles, tables, and chairs.

9. Casa Franci Montalcino

Montalcino

Peter

RM767

RM890 total

includes taxes & fees

12 Oct - 13 Oct

An aerial view of a historic town with stone buildings, a prominent church, and a castle-like structure with a sign reading "Castello di Monteverde."

A stone building with a brick archway and a tall cypress tree in front.

An aerial view of a two-story stone building with a swimming pool in the foreground.

An outdoor patio with terracotta-tiled flooring, metal tables and chairs, potted plants, and a view of the sea.

10. Hotel Vecchia Oliviera

Montalcino

Roy

RM584

RM679 total

includes taxes & fees

21 Oct - 22 Oct

A pool with a modern water feature and a stone structure.

A wicker dining table set with breakfast items, a vase of flowers, and a scenic view.

A buffet table with various desserts and a long dining area with tables and chairs.

A large, multi-story building with a swimming pool, surrounded by lush greenery.

11. Mercure Petriolo Siena Terme Spa Hotel

Civitella Paganico

Mike

RM343

RM378 total

includes taxes & fees

12 Oct - 13 Oct

A room with a bed, a chair, a view through an open window, and a white dresser with bottles and glasses.

A hotel room with a bed, a nightstand with bottles, a chair, and a wardrobe.

A view from a window overlooking a rural landscape with fields and distant hills.

A courtyard with a stone wall, a small pond, and a waterfall. There are trees and plants around, and a building in the background.

12. Albergo Giardino

Montalcino

Norma

RM373

RM447 total

includes taxes & fees

4 Nov - 5 Nov

A courtyard with outdoor seating, a covered area, and a building with brick walls and green shutters.

A living room with a white sofa, a coffee table, and a painting of a historical scene. There is a lamp, a small table with a plant, and a sign indicating room numbers.

A historic building with a sign reading "Borgo Antico" and a "Ristorante" sign below.

A bedroom with a bed, a sofa, a desk, and a TV. There are windows with curtains and a view of greenery outside.

13. Hotel Borgo Antico

Monteroni d'Arbia

Charles

RM383

RM444 total

includes taxes & fees

31 Oct - 1 Nov

A person serving food at a table with various dishes and a wine rack in the background.

A spacious room with a large wooden table, multiple drawers, and a colorful abstract painting on the wall.

A bedroom with a large bed, a wardrobe, a chair, and a ceiling with exposed beams.

A kitchen with a built-in shelf displaying various food items and kitchenware.

14. Palazzo Lucchini

Montalcino

RM1,614

RM1,821 total

includes taxes & fees

13 Oct - 14 Oct

A restaurant with tables and wicker chairs, large windows, and a view of buildings and greenery.

A multi-story building with a central entrance, large windows with shutters, and a paved courtyard.

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.

15. Palazzo Saloni

Montalcino

Michael

RM1,053

RM1,204 total

includes taxes & fees

9 Nov - 10 Nov

A spa area with a stone wall, wooden beams, a large window with a view, and a hot tub.

A pool surrounded by manicured gardens and vineyards, with a clear view of rolling hills in the background.

A stone house with a covered patio, a stone pathway, and well-maintained landscaping.

A picnic setup with a basket, blanket, pillows, and food items on a grassy area with a hilly landscape in the background.

16. Mastrojanni Relais - Small Luxury Hotels of the World

Montalcino

Gurnek

RM1,804

RM2,030 total

includes taxes & fees

7 Nov - 8 Nov

A bedroom with a bed, a chair, a table, and a stone wall.

An outdoor patio with stone walls, a pergola, and a table set for dining.

An underground wine cellar with brick walls, wooden tables, and chairs.

A piano with sheet music, an easel with a drawing, and a wine bottle in a stone-walled room.

17. Dimora delle Muse

Montalcino

Bradley N.

RM717

RM826 total

includes taxes & fees

2 Nov - 3 Nov

A pool with a wooden deck and lounge chairs, surrounded by trees and hills in the background.

A table with a bottle of Brunello di Montalcino wine, a plate of food, and a bowl of bread.

A rustic interior with a brick fireplace, wooden beams, and a bar area.

A window with a view of a green landscape, including trees and distant hills.

18. Fattoria Pieve a Salti

Montalcino

Marko

RM517

RM587 total

includes taxes & fees

1 Nov - 2 Nov

A living room with a sofa, armchairs, a coffee table, a cabinet, and a lamp.

A buffet setup with various food items and condiments.

A room with a herringbone floor, a bed, a sofa, a desk, and a view through a window.

A hotel room with a bed, bedside lamps, a desk with a coffee maker, and a window with curtains.

19. Relais Cloister Pienza

Pienza

Karen

RM524

RM604 total

includes taxes & fees

25 Oct - 26 Oct

An infinity pool with a clear view of the sunset, surrounded by trees and lounge chairs.

A view through a window of a courtyard with a pool, trees, and a building in the background.

An outdoor dining area with tables and chairs, covered by a canopy, overlooking a scenic landscape.

A covered outdoor area with a glass roof, bicycles parked, and potted plants.

20. Palazzuolo

San Quirico d'Orcia

Alberto

RM406

RM465 total

includes taxes & fees

26 Oct - 27 Oct

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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.

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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.

Top Castiglione del Bosco Hotel Reviews

Hotel Italia

10/10 Excellent

"We stayed here for three nights and absolutely loved it. The hotel is charming, convenient and comfortable. Breakfast was very good, with a nice choice of foods, and the lounge/bar is a great place to relax. The staff were very helpful with directions and bookings. We would gladly stay here again."

Il Chiostro del Carmine

10/10 Excellent

"Great breakfast, stunning views of the Tuscan countryside and felt like walking into the past. Exactly as per the photos, a wonderful ambience, full of charm and character. Well located on the edge of the old town, less than 10 minutes walk to the centre. The staff were so friendly and helpful. I would not hesitate to recommend this hotel and hope to come back myself."

Palazzo Ravizza

10/10 Excellent

"Beautiful hotel in the city center with free parking which can be difficult to find. The staff was terrific"

Hotel Athena

10/10 Excellent

"Lovely hotel in Siena. Well located for exploring on foot with the main Palazzo and the Duomo no more than 15 minutes away. Really enjoyed the rooftop patio!"

Hotel San Gregorio

8/10 Good

"Great location, clean room and communal space. We were disappointed that we were given a room with jacuzzi but no shower and refrigerator was broken. Overall a nice experience"

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent

"Beautiful hotel and very helpful staff. Excellent location in the heart of Siena. Disappointed with our hotel room. Not up to our expectations."

Castiglion del Bosco, A Rosewood Hotel

10/10 Excellent

"Nice and quiet excellent hospitality"

Four Points by Sheraton Siena

8/10 Good

"Property seem reasonable, staff helpful, rooms are little small and dated, bathrooms need renovation."

Albergo Le Terme

10/10 Excellent

"It was amazing."

More cheap stays in Castiglione del Bosco

Cannon d'Oro

Via Montanini 28 Siena SI

RM234

RM271 total

4 Nov - 5 Nov

includes taxes & fees

7.8/10 Good! (258 reviews)

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI

RM315

RM361 total

4 Nov - 5 Nov

includes taxes & fees

10/10 Exceptional! (50 reviews)

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI

RM344

RM393 total

4 Nov - 5 Nov

includes taxes & fees

7.8/10 Good! (451 reviews)

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI

RM387

RM440 total

3 Nov - 4 Nov

includes taxes & fees

8.8/10 Excellent! (111 reviews)

Hotel La Terrazza di Montepulciano

Via Pié al Sasso 16 Montepulciano SI

RM458

RM522 total

15 Oct - 16 Oct

includes taxes & fees

9.4/10 Exceptional! (214 reviews)

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI

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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.

Castiglione del Bosco hotels from RM271

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Castiglione del Bosco

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Castiglione del Bosco hotels

1. Castiglion del Bosco, A Rosewood Hotel

2. SI Montalcino Hotel

3. Podere Brizio

4. Villa Le Prata - Residenza del Vescovo

5. Hotel Ghibellino

6. Hotel Dei Capitani

7. Capanna Suites

8. Le Ragnaie

9. Casa Franci Montalcino

10. Hotel Vecchia Oliviera

11. Mercure Petriolo Siena Terme Spa Hotel

12. Albergo Giardino

13. Hotel Borgo Antico

14. Palazzo Lucchini

15. Palazzo Saloni

16. Mastrojanni Relais - Small Luxury Hotels of the World

17. Dimora delle Muse

18. Fattoria Pieve a Salti

19. Relais Cloister Pienza

20. Palazzuolo

Stay near popular Castiglione del Bosco attractions

Castiglion del Bosco Winery

Learn more about Castiglione del Bosco

Top Castiglione del Bosco Hotel Reviews

Hotel Italia

Il Chiostro del Carmine

Palazzo Ravizza

Hotel Athena

Hotel San Gregorio

Grand Hotel Continental Siena – Starhotels Collezione

Castiglion del Bosco, A Rosewood Hotel

Four Points by Sheraton Siena

Albergo Le Terme

More cheap stays in Castiglione del Bosco

Cannon d'Oro

Torre del Fuggisole

Piccolo Hotel Etruria

Albergo Centrale

Hotel La Terrazza di Montepulciano

Porta Pispini Residence

Frequently asked questions

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