Book The Best Hotels in Castiglione del Bosco for 2026 from CA $94 - Fully Refundable Options

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

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Go beyond your typical stay in Castiglione del Bosco

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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 aerial view of a villa with a swimming pool, terraced gardens, and a stone pathway.

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

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

CA $1,885

CA $2,090 total

includes taxes & fees

Nov 5 - Nov 6

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

A kitchen with a buffet setup, including a variety of food items and glassware.

2. SI Montalcino Hotel

Montalcino

Farasley

CA $132

CA $182 total

includes taxes & fees

Oct 26 - Oct 27

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

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.

A stone building with a pool, lounge chairs, and a garden with flowers.

3. Podere Brizio

Montalcino

Aseem

CA $265

CA $304 total

includes taxes & fees

Oct 31 - Nov 1

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.

4. Le Ragnaie

Montalcino

Trevor

CA $138

CA $168 total

includes taxes & fees

Nov 3 - Nov 4

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

5. Hotel Ghibellino

Buonconvento

Anna-Maree

CA $122

CA $139 total

includes taxes & fees

Oct 31 - Nov 1

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

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

6. Hotel Dei Capitani

Montalcino

Phillip

CA $175

CA $206 total

includes taxes & fees

Oct 20 - Oct 21

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

A staircase with stone steps leading to a room with a large window, wooden beams on the ceiling, and a stone wall.

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.

7. Casa Franci Montalcino

Montalcino

Peter

CA $268

CA $311 total

includes taxes & fees

Oct 14 - Oct 15

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

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.

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

8. Albergo Giardino

Montalcino

Norma

CA $130

CA $156 total

includes taxes & fees

Nov 4 - Nov 5

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

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

An indoor swimming pool with clear glass walls, a tiled floor, and a stone wall with a mosaic pattern.

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

9. Mercure Petriolo Siena Terme Spa Hotel

Civitella Paganico

Mike

CA $120

CA $131 total

includes taxes & fees

Oct 25 - Oct 26

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

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.

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.

10. Hotel Borgo Antico

Monteroni d'Arbia

Charles

CA $94

CA $112 total

includes taxes & fees

Oct 15 - Oct 16

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.

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.

11. Capanna Suites

Montalcino

Michael

CA $462

CA $524 total

includes taxes & fees

Oct 26 - Oct 27

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 wooden tables, wine bottles, and a piano.

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

12. Dimora delle Muse

Montalcino

Bradley N.

CA $248

CA $285 total

includes taxes & fees

Nov 6 - Nov 7

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 stone building with a garden and a gazebo.

A picnic setup with blankets and cushions on a gravel surface, surrounded by cypress trees and a sunset in the background.

13. Villa Le Prata - Residenza del Vescovo

Montalcino

Karen

CA $599

CA $675 total

includes taxes & fees

Nov 13 - Nov 14

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.

14. Fattoria Pieve a Salti

Montalcino

Marko

CA $165

CA $187 total

includes taxes & fees

Oct 16 - Oct 17

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 wine tasting room with a marble bar, wine bottles, glasses, wicker furniture, and a view of the sea through a large arched window.

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

15. Palazzo Saloni

Montalcino

Michael

CA $341

CA $391 total

includes taxes & fees

Nov 13 - Nov 14

A villa with a swimming pool, terraced garden, and a view of distant mountains.

A cozy living room with a fireplace, comfortable seating, and a table set with various desserts.

A fire pit with burning logs, surrounded by stone blocks and a metal grill.

A stone building with a gravel pathway leading to the entrance.

16. Agriturismo Il Macchione

Pienza

YOUNG BAE

CA $203

CA $229 total

includes taxes & fees

Nov 5 - Nov 6

A stone building with a pathway leading to a door, surrounded by trees and illuminated by warm lights.

A breakfast buffet with pastries, bread, and condiments.

A woman in a green swimsuit standing in a pool with a stone wall and a glass ceiling.

A stone building with a view of a courtyard, a pool, and surrounding greenery.

17. L'Orto delle Terme

San Quirico d'Orcia

Stimson

CA $181

CA $205 total

includes taxes & fees

Nov 8 - Nov 9

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 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.

18. Mastrojanni Relais - Small Luxury Hotels of the World

Montalcino

Gurnek

CA $628

CA $707 total

includes taxes & fees

Nov 10 - Nov 11

A garden pathway leading to a rustic building with a tiled roof, surrounded by lush greenery and red flowers.

A modern bedroom with a large bed, a TV, a fireplace, and a bathtub.

A modern hotel room with a large window, a bathtub, a seating area, and a view of the outdoors.

An outdoor restaurant with tables and chairs, covered by a wooden roof, and surrounded by greenery.

19. Boutique Villa Liberty - Depandance Hotel - Borgo Capitano Collection - Albergo diffuso

San Quirico d'Orcia

Alessio

CA $177

CA $201 total

includes taxes & fees

Nov 2 - Nov 3

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.

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

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

20. Palazzuolo

San Quirico d'Orcia

Alberto

CA $166

CA $189 total

includes taxes & fees

Oct 14 - Oct 15

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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 out? 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

"Staff and hotel was great."

Hotel San Gregorio

10/10 Excellent

"Great location. Clean and quiet with good breakfast"

Hotel Athena

10/10 Excellent

"Reception staff very friendly and helpful. Room on top floor had two full length windows with spectacular views. Older property but updated nicely; not modern but comfortable. Comfy bed, linens and pillows. Nice breakfast with lots of variety. There are two floors that have breakfast - the lowest level is more spacious and had food replaced more quickly than upper level. Hotel seems far, but everything is 5 to 15 minutes away. We found our favorite wine spot just a 5 minute walk away at Tuscan Wine School. But do go to the rooftop terrace for lovely views."

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."

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."

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."

Hotel Certosa Di Maggiano

10/10 Excellent

"Our stay for our honeymoon was amazing. We loved our room and we were upgraded to a suite because they had it available. All the staff were kind and helpful. They carried our luggage up two flights of stairs to our room, helped make reservations, called taxis for us, etc. The property was beautiful, maintained nicely, and was very quiet. Really have no complaints. To note it is outside of city Centre of Siena so you will need taxis back and forth to the city for meals etc. which can get quite pricey so just plan ahead. Our room could’ve been cleaned a little better in between each day but overall it was still very clean. We would definitely stay there again!!"

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent

"Amazing views. Relaxing stay! A very romantic hotel, though I was surprised by the number of families there; given its location and amenities, I had assumed it was geared towards couples. That isn't a negative comment, though—it was simply a case of my own mistaken perception."

More cheap stays in Castiglione del Bosco

Cannon d'Oro

Via Montanini 28 Siena SI

CA $81

CA $94 total

Nov 13 - Nov 14

includes taxes & fees

7.8/10 Good! (259 reviews)

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI

CA $106

CA $121 total

Nov 12 - Nov 13

includes taxes & fees

7.8/10 Good! (452 reviews)

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI

CA $110

CA $126 total

Nov 4 - Nov 5

includes taxes & fees

10/10 Exceptional! (50 reviews)

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI

CA $123

CA $140 total

Nov 12 - Nov 13

includes taxes & fees

8.8/10 Excellent! (113 reviews)

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI

CA $157

CA $179 total

Oct 15 - Oct 16

includes taxes & fees

Hotel La Terrazza di Montepulciano

Via Pié al Sasso 16 Montepulciano SI

CA $159

CA $182 total

Oct 25 - Oct 26

includes taxes & fees

9.4/10 Exceptional! (215 reviews)

Frequently asked questions

What is the best area to stay in Castiglione Del Bosco?

The best area to stay in Castiglione Del Bosco is within the estate itself, specifically around the Borgo, as it offers the most convenient access to all amenities and services.The Borgo is the heart of Castiglione Del Bosco, a beautifully restored historic village that serves as the central hub for guests. It's where you'll find the main reception, the estate's finest restaurants, and many of the facilities. The buildings are traditional Tuscan stone, and the entire area is designed for easy pedestrian access, allowing you to stroll between dining options, the spa, and the main pool with ease.For couples seeking a luxurious and relaxing escape, staying within the Borgo or in one of the nearby suites is ideal. You'll be steps away from gourmet dining experiences, wine tastings at the estate's winery, and the indulgent spa treatments. The picturesque surroundings and the ease of access to all facilities make it superb for a stress-free romantic getaway.Families will also find staying within the Borgo or in a nearby villa highly convenient. The proximity to the main pool, children's activities, and various dining options simplifies planning.

When is the best time to go to Castiglione Del Bosco?

The best time to go to Castiglione Del Bosco is during the spring (April to June) and autumn (September to October) months.These periods offer pleasant weather, ideal for exploring the Tuscan countryside and enjoying the estate's amenities. Spring brings blooming wildflowers and comfortable temperatures, while autumn provides beautiful foliage and the excitement of the grape harvest season. Both seasons allow for outdoor activities without the intense heat of summer.Couples often find these shoulder seasons particularly appealing. The weather is superb for leisurely walks through the vineyards, relaxing by the pool, or enjoying al fresco dining with stunning views. The estate's focus on fine wine and culinary experiences aligns perfectly with the relaxed pace of these months.For travellers interested in the region's agricultural heritage, autumn is especially rewarding. You might witness grape harvesting or olive picking, offering a deeper connection to the local traditions and the estate's operations.

Can I cancel my hotel reservation on Expedia?

You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Castiglione del Bosco.

How much is the nightly rate at a Castiglione del Bosco hotel?

Prices for hotels in Castiglione del Bosco often vary, but you can find a great deal from CA $94 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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Find hotels in Castiglione del Bosco from CA $94

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. Le Ragnaie

5. Hotel Ghibellino

6. Hotel Dei Capitani

7. Casa Franci Montalcino

8. Albergo Giardino

9. Mercure Petriolo Siena Terme Spa Hotel

10. Hotel Borgo Antico

11. Capanna Suites

12. Dimora delle Muse

13. Villa Le Prata - Residenza del Vescovo

14. Fattoria Pieve a Salti

15. Palazzo Saloni

16. Agriturismo Il Macchione

17. L'Orto delle Terme

18. Mastrojanni Relais - Small Luxury Hotels of the World

19. Boutique Villa Liberty - Depandance Hotel - Borgo Capitano Collection - Albergo diffuso

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

Hotel San Gregorio

Hotel Athena

Il Chiostro del Carmine

Grand Hotel Continental Siena – Starhotels Collezione

Four Points by Sheraton Siena

Albergo Le Terme

Hotel Certosa Di Maggiano

Castello di Velona Resort Thermal SPA & Winery

More cheap stays in Castiglione del Bosco

Cannon d'Oro

Piccolo Hotel Etruria

Torre del Fuggisole

Albergo Centrale

Porta Pispini Residence

Hotel La Terrazza di Montepulciano

Frequently asked questions

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