Top 10 Hotels in Castiglione del Bosco (from $61) 2026 - Competitive Prices

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 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

$1,225 nightly

$1,359 total

Nov 3 - Nov 4

Total with taxes and fees

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

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

A hotel room with a large bed, a bedside table, a lamp, a window with curtains, and a view of greenery outside.

A poolside area with lounge chairs, a table with wine glasses and a bottle, and a view of a mountainous landscape.

2. SI Montalcino Hotel

Montalcino

Farasley

$97 nightly

$116 total

Oct 26 - Oct 27

Total with taxes and fees

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.

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.

3. Le Ragnaie

Montalcino

Trevor

$95 nightly

$115 total

Nov 3 - Nov 4

Total with taxes and fees

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

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

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.

4. Podere Brizio

Montalcino

Aseem

$200 nightly

$229 total

Oct 31 - Nov 1

Total with taxes and fees

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

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

5. Hotel Ghibellino

Buonconvento

Anna-Maree

$85 nightly

$97 total

Oct 31 - Nov 1

Total with taxes and fees

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

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.

A buffet setup with various food items, a coffee station, and a counter with beverages.

6. Hotel Dei Capitani

Montalcino

Phillip

$116 nightly

$137 total

Oct 21 - Oct 22

Total with taxes and fees

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.

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

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

7. Mercure Petriolo Siena Terme Spa Hotel

Civitella Paganico

Penny

$84 nightly

$93 total

Oct 19 - Oct 20

Total with taxes and fees

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

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

A pathway flanked by tall, narrow trees leading to a stone building with an arched entrance.

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

8. Villa Le Prata - Residenza del Vescovo

Montalcino

Karen

$430 nightly

$485 total

Nov 5 - Nov 6

Total with taxes and fees

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

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

9. Palazzo Saloni

Montalcino

Michael

$253 nightly

$289 total

Nov 18 - Nov 19

Total with taxes and fees

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

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

10. Casa Franci Montalcino

Montalcino

Joseph

$200 nightly

$232 total

Oct 21 - Oct 22

Total with taxes and fees

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

A room with a large window, a door, and a view of a landscape.

11. Capanna Suites

Montalcino

Michael

$325 nightly

$369 total

Oct 26 - Oct 27

Total with taxes and fees

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

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

A stone building with the name "Albergoggiardino" above the entrance. Inside, there is a chandelier, a clock, and a blue chair.

12. Albergo Giardino

Montalcino

Norma

$114 nightly

$134 total

Nov 18 - Nov 19

Total with taxes and fees

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.

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

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

13. Dimora delle Muse

Montalcino

Bradley N.

$171 nightly

$197 total

Nov 2 - Nov 3

Total with taxes and fees

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

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

An aerial view of a property with a main building, a swimming pool, and surrounding green fields.

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

14. Fattoria Pieve a Salti

Montalcino

Marko

$111 nightly

$127 total

Nov 9 - Nov 10

Total with taxes and fees

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

A stone building with a tiled roof, surrounded by a grassy area and flowering plants.

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.

15. Agriturismo Il Macchione

Pienza

YOUNG BAE

$140 nightly

$158 total

Nov 18 - Nov 19

Total with taxes and fees

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

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

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.

16. L'Orto delle Terme

San Quirico d'Orcia

Tracey

$118 nightly

$135 total

Nov 18 - Nov 19

Total with taxes and fees

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

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

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

A restaurant with a high ceiling, brick walls, and a bar area with a variety of bottles. There are tables and chairs for dining, and a television is visible on the right side.

17. Hotel Borgo Antico

Monteroni d'Arbia

Charles

$101 nightly

$117 total

Oct 19 - Oct 20

Total with taxes and fees

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

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

A spa setting with a stone wall, a fireplace, and a massage table.

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

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

San Quirico d'Orcia

Alessio

$124 nightly

$141 total

Nov 2 - Nov 3

Total with taxes and fees

A stone building with a courtyard and a canal.

A bar area with wooden shelves, books, and a brick wall. There are three green bar stools and a patterned rug on the floor.

A bedroom with a wooden ceiling, a bed with a decorative headboard, a bench, and a large wardrobe.

A spacious room with a large bed, two armchairs, a sofa, and a view of the outdoors through a large window.

19. Palazzo Brandano

Trequanda

Peter

$69 nightly

$79 total

Nov 4 - Nov 5

Total with taxes and fees

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

20. Mastrojanni Relais - Small Luxury Hotels of the World

Montalcino

Gurnek

$443 nightly

$499 total

Nov 7 - Nov 8

Total with taxes and fees

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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 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

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent

"La vue est panoramique et le château est grandiose"

Hotel San Gregorio

10/10 Excellent

"Get"

L'Orto delle Terme

10/10 Excellent

"Clean room and beautiful Suite. Breakfast was excellent!"

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."

Hotel Italia

10/10 Excellent

"Staff and hotel was great."

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."

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!!"

More cheap stays in Castiglione del Bosco

Cannon d'Oro

Via Montanini 28 Siena SI

$53 nightly

$61 total

Nov 18 - Nov 19

Total with taxes and fees

7.8/10 Good! (259 reviews)

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI

$68 nightly

$78 total

Nov 18 - Nov 19

Total with taxes and fees

7.8/10 Good! (453 reviews)

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI

$85 nightly

$97 total

Nov 5 - Nov 6

Total with taxes and fees

10/10 Exceptional! (50 reviews)

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI

$88 nightly

$100 total

Nov 18 - Nov 19

Total with taxes and fees

8.8/10 Excellent! (113 reviews)

Hotel La Terrazza di Montepulciano

Via Pié al Sasso 16 Montepulciano SI

$112 nightly

$128 total

Oct 22 - Oct 23

Total with taxes and fees

9.4/10 Exceptional! (217 reviews)

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI

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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 Village, which is the heart of the property.The Village is the central hub of Castiglione Del Bosco, offering a collection of restored historic buildings that house the main amenities. You'll find the primary dining options, a well-stocked shop, and a cozy bar here. The village is set amidst rolling hills with vineyards and olive groves stretching in every direction, providing a picturesque backdrop. It's designed for convenience, with everything within a short walk or shuttle ride.For couples seeking a romantic and secluded experience, staying in one of the private villas scattered across the estate is an excellent choice. These villas offer privacy, often with private pools, and stunning views of the Tuscan countryside, while still providing access to all the amenities of The Village. They are well-suited for relaxing and enjoying the quiet surroundings.Families will find the suites and larger accommodations within The Village or nearby ideal. These options often provide more space and easier access to the estate's facilities, including dining and activities.

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

For an optimal experience in Castiglione Del Bosco, the best times to visit are during the spring (April to June) and fall (September to October) seasons.During spring, the Tuscan countryside awakens with lush greenery and blooming wildflowers, offering pleasant temperatures superb for exploring the vineyards and olive groves. The weather is generally mild and sunny, making it ideal for outdoor activities like hiking, cycling, and enjoying al fresco dining without the intense heat of summer. This period is particularly good for couples seeking picturesque scenery and comfortable conditions for leisurely tours of the region's historic towns.The fall months bring a different kind of beauty, with the landscape transforming into rich hues of gold, red, and brown as the grape harvest begins. This is an exciting time for wine enthusiasts, as many local wineries offer special tours and tastings celebrating the vendemmia. The temperatures remain comfortable, and the crowds tend to be smaller than in the peak summer season, allowing for a more serene experience.

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 $61 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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Book Hotels in Castiglione del Bosco on Expedia.it

Find hotels in Castiglione del Bosco from $61

Upfront pricing

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. Le Ragnaie

4. Podere Brizio

5. Hotel Ghibellino

6. Hotel Dei Capitani

7. Mercure Petriolo Siena Terme Spa Hotel

8. Villa Le Prata - Residenza del Vescovo

9. Palazzo Saloni

10. Casa Franci Montalcino

11. Capanna Suites

12. Albergo Giardino

13. Dimora delle Muse

14. Fattoria Pieve a Salti

15. Agriturismo Il Macchione

16. L'Orto delle Terme

17. Hotel Borgo Antico

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

19. Palazzo Brandano

20. Mastrojanni Relais - Small Luxury Hotels of the World

Stay near popular Castiglione del Bosco attractions

Castiglion del Bosco Winery

Learn more about Castiglione del Bosco

Top Castiglione del Bosco Hotel Reviews

Castello di Velona Resort Thermal SPA & Winery

Hotel San Gregorio

L'Orto delle Terme

Hotel Chiusarelli

Hotel Italia

Il Chiostro del Carmine

Four Points by Sheraton Siena

Albergo Le Terme

Hotel Certosa Di Maggiano

More cheap stays in Castiglione del Bosco

Cannon d'Oro

Piccolo Hotel Etruria

Torre del Fuggisole

Albergo Centrale

Hotel La Terrazza di Montepulciano

Porta Pispini Residence

Frequently asked questions

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