Top 10 Hotels in Castiglione del Bosco from ￥14,700 - 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.

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.

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

1. Castiglion del Bosco, A Rosewood Hotel

Montalcino

Abdel

￥364,458

￥402,686 total

includes taxes & fees

Oct 8 - Oct 9

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

Sam

￥15,356

￥20,990 total

includes taxes & fees

Sep 29 - Sep 30

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

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.

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

3. Mercure Petriolo Siena Terme Spa Hotel

Civitella Paganico

Mike

￥13,363

￥14,700 total

includes taxes & fees

Sep 17 - Sep 18

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.

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.

4. Le Ragnaie

Montalcino

Douglas

￥18,773

￥22,432 total

includes taxes & fees

Sep 28 - Sep 29

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

5. Albergo Giardino

Montalcino

Norma

￥16,024

￥19,052 total

includes taxes & fees

Oct 16 - Oct 17

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

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

6. Podere Brizio

Montalcino

Aseem

￥34,695

￥39,589 total

includes taxes & fees

Oct 11 - Oct 12

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

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

7. Villa Le Prata - Residenza del Vescovo

Montalcino

Jeffery

￥89,485

￥100,215 total

includes taxes & fees

Sep 20 - Sep 21

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 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.

8. Capanna Suites

Montalcino

Michael

￥71,544

￥80,480 total

includes taxes & fees

Oct 9 - Oct 10

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 room with a wooden bench, potted plants, framed artwork, and a view of the outside.

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

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

9. Hotel Vecchia Oliviera

Montalcino

Roy

￥27,144

￥31,283 total

includes taxes & fees

Oct 14 - Oct 15

A spacious indoor area with a brick archway leading to a kitchen, wooden tables and chairs, and large windows offering a view of the outdoors.

A rocking chair with a cushion and a pillow, positioned against a wall with a tiled floor.

An outdoor patio with brick flooring and metal furniture, surrounded by a brick building and greenery.

A bedroom with a large bed, wooden ceiling beams, an arched brick ceiling, and a TV on the wall.

10. Hotel More Di Cuna

Monteroni d'Arbia

Somayyeh

￥12,729

￥14,892 total

includes taxes & fees

Sep 17 - Sep 18

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.

11. Hotel Borgo Antico

Monteroni d'Arbia

Charles

￥14,903

￥17,284 total

includes taxes & fees

Oct 15 - Oct 16

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

A wine cellar with wooden racks and tables, a sign reading "DROGHERIA," and a rustic ceiling.

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.

12. Drogheria & Locanda Franci

Montalcino

Peter

￥29,885

￥34,656 total

includes taxes & fees

Sep 16 - Sep 17

A dining area with a table set for four, chairs, a television mounted on the wall, and a cabinet with glass doors.

A brick wall with a number plate and a metal gate.

A staircase with a metal railing leading to a landing.

A bedroom with a bed, two bedside tables with lamps, a window with curtains, and a painting on the wall.

13. L'Aia di Argia

Monteroni d'Arbia

mario

￥11,695

￥13,577 total

includes taxes & fees

Sep 16 - Sep 17

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

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."

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

14. Hotel Dei Capitani

Montalcino

Frankie

￥22,778

￥26,480 total

includes taxes & fees

Sep 29 - Sep 30

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.

15. Dimora delle Muse

Montalcino

Bradley N.

￥32,161

￥36,803 total

includes taxes & fees

Oct 10 - Oct 11

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.

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

16. Fattoria Pieve a Salti

Montalcino

Marko

￥18,777

￥21,368 total

includes taxes & fees

Sep 17 - Sep 18

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

A man walking through a hallway with an arched ceiling and an elevator in the background.

A living room with a red sofa, a coffee table with magazines, a lamp, and a framed botanical display on the wall.

A bedroom with a single bed, a wooden desk, a window with a view, and a door leading to a bathroom.

17. Palazzo Lucchini

Montalcino

￥61,557

￥69,495 total

includes taxes & fees

Sep 17 - Sep 18

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 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.

18. Palazzo Saloni

Montalcino

Michael

￥54,735

￥61,991 total

includes taxes & fees

Sep 16 - Sep 17

A stone wall with a view of rolling hills and mountains.

An outdoor dining area with tables and chairs, a flower arrangement, and a view of the countryside.

A courtyard with stone buildings, potted plants, and outdoor seating.

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

19. Castello Banfi - Il Borgo - Relais et Chateaux

Montalcino

Jason

￥230,143

￥254,939 total

includes taxes & fees

Oct 2 - Oct 3

A table with two wine glasses, a bottle, and a book.

Neatly folded white towels and an orange rose on a textured surface.

A modern dining area with a wooden table and white chairs, a chandelier, and a potted plant with pink flowers.

A modern hotel room with a large bed, a desk with a flat-screen TV, a chair, and a mirror.

20. Domus il Palio B&B

Ravacciano

Alissia

￥9,808

￥11,502 total

includes taxes & fees

Oct 7 - Oct 8

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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

Hotel Chiusarelli

10/10 Excellent

"Extremely helpful staff at the reception desk! Breakfast was very good. Comfortable bed and room. Excellent location"

Villa Scacciapensieri Boutique Hotel

10/10 Excellent

"Just loved it!! This is a great place!!!"

Palazzo Ravizza

10/10 Excellent

"This property was in a great location, clean with large rooms and beautiful views. Staff was extremely helpful and breakfast was wonderful!"

Castiglion del Bosco, A Rosewood Hotel

10/10 Excellent

"Very warm and friendly service."

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent

"Excellent location. Even though a walking only area, easy walk. Great service and breakfast was delicious. My only complaint is the included breakfast was only for 1 person."

Hotel Italia

8/10 Good

"Clean, well maintained property that you’ll feel safe spending the night."

Hotel Athena

10/10 Excellent

"We had a wonderful stay at Hotel Athena in Siena. The service was exceptional, the staff were warm, welcoming and genuinely helpful throughout our visit. The location was fantastic for exploring Siena, with everything within walking distance, while the hotel itself provided a comfortable and relaxing place to come back to after a day of exploring. We also loved the beautiful views from the terrace which was the perfect spot to unwind with a drink and take in the scenery. Sunset was especially beautiful and I would recommend calling the terrace staff themselves to reserve your seat. They are VERY busy up there so please exercise patience and kindness to the server and bartender as they work so hard to get your orders to you as quickly as possible. Self parking our car was a huge bonus as we rented a vehicle to explore Tuscany. A lovely hotel, a great location and wonderful service. We would happily stay here again when visiting Siena!"

Castello di Leonina Relais

10/10 Excellent

"."

Villa Tiberini Wine Relais

10/10 Excellent

"Villa Tiberini is a beautiful place! The chef, staff and owners are wonderful people. The apartment was clean, had all of the necessities and thoughtful touches to make the experience welcoming and comfortable. The shower water pressure and pillow top bed were an extra treat! Breakfast was delicious and we loved the wine. We thoroughly enjoyed our time and would highly recommend this stay for anyone looking to get away from the buzz of tourist destinations. The actual winery is about a 10 minute drive away. We enjoyed our time lounging by the pool and exploring nearby towns by car."

More cheap stays in Castiglione del Bosco

Cannon d'Oro

Via Montanini 28 Siena SI

￥14,787

￥17,157 total

Sep 24 - Sep 25

includes taxes & fees

7.8/10 Good! (258 reviews)

Hotel La Terrazza di Montepulciano

Via Pié al Sasso 16 Montepulciano SI

￥17,818

￥20,313 total

Sep 22 - Sep 23

includes taxes & fees

9.4/10 Exceptional! (211 reviews)

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI

￥18,077

￥20,776 total

Oct 15 - Oct 16

includes taxes & fees

7.8/10 Good! (437 reviews)

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI

￥24,273

￥27,591 total

Oct 5 - Oct 6

includes taxes & fees

8.8/10 Excellent! (108 reviews)

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI

￥27,795

￥31,466 total

Sep 28 - Sep 29

includes taxes & fees

10/10 Exceptional! (49 reviews)

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI

Get rates

9.4/10 Exceptional! (23 reviews)

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 traveler data. This hotel offers a winery and 2 outdoor pools. Two other options for your stay in the area are Hotel Athena and Castello di Velona Resort Thermal SPA & Winery. See all available top hotels, or vacation rentals in Castiglione del Bosco.

What's the top vacation rental in Castiglione del Bosco?

INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING: Visitors like this Castiglione del Bosco vacation home rental. It is located in the city center and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a terrace, a garden, and a selection of books so you can immerse yourself in your vacation. See all vacation rentals in Castiglione del Bosco.

If I need to cancel my hotel reservation in Castiglione del Bosco, will I receive a refund?

Yes, you'll find most hotel bookings are refundable if you cancel before the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of check in. If you booked a non-refundable reservation, it might still be possible to cancel it and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Castiglione del Bosco.

Where can I learn more about changing or cancelling my trip to Castiglione del Bosco?

For additional details about changing or cancelling your trip to Castiglione del Bosco, go to https://www.expedia.com/service/.

What's the best boutique-style accommodation in Castiglione del Bosco?

Castiglion del Bosco, A Rosewood Hotel is a favorite hotel with our travelers looking for a stylish accommodation, and features 42 guestrooms, a winery, and 2 restaurants. See all boutique hotels in Castiglione del Bosco.

What's the best place to stay near Peretola Airport (FLR)?

Hotel Cosmopolitan is a popular 4-star hotel featuring free WiFi and a bar. It's located a short 0.7 mi (1.2 km) from Peretola Airport. Other good choices close to the airport are Best Western Plus CHC Florence and Hotel Mirage.

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 3403 hotels and other accommodations in the surrounding area. Find out more about Castiglione del Bosco.

What is there to see in Castiglione del Bosco?

A favorite place to visit is Castiglion del Bosco Winery. You'll also find Fortress of Montalcino and Tenuta Greppo Franco Biondi Santi in the area. Check out what more 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 temp of 72°F, while the coldest months are January and February with an average of 44°F. Average annual precipitation for Castiglione del Bosco is 37 inches.

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Find hotels in Castiglione del Bosco from ￥14,700

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Castiglione del Bosco

Check prices for these dates

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Property class

Guest rating

Our top choices for Castiglione del Bosco hotels

1. Castiglion del Bosco, A Rosewood Hotel

2. SI Montalcino Hotel

3. Mercure Petriolo Siena Terme Spa Hotel

4. Le Ragnaie

5. Albergo Giardino

6. Podere Brizio

7. Villa Le Prata - Residenza del Vescovo

8. Capanna Suites

9. Hotel Vecchia Oliviera

10. Hotel More Di Cuna

11. Hotel Borgo Antico

12. Drogheria & Locanda Franci

13. L'Aia di Argia

14. Hotel Dei Capitani

15. Dimora delle Muse

16. Fattoria Pieve a Salti

17. Palazzo Lucchini

18. Palazzo Saloni

19. Castello Banfi - Il Borgo - Relais et Chateaux

20. Domus il Palio B&B

Stay near popular Castiglione del Bosco attractions

Castiglion del Bosco Winery

Learn more about Castiglione del Bosco

Top Castiglione del Bosco Hotel Reviews

Hotel Chiusarelli

Villa Scacciapensieri Boutique Hotel

Palazzo Ravizza

Castiglion del Bosco, A Rosewood Hotel

Grand Hotel Continental Siena – Starhotels Collezione

Hotel Italia

Hotel Athena

Castello di Leonina Relais

Villa Tiberini Wine Relais

More cheap stays in Castiglione del Bosco

Cannon d'Oro

Hotel La Terrazza di Montepulciano

Piccolo Hotel Etruria

Albergo Centrale

Torre del Fuggisole

Porta Pispini Residence

Frequently asked questions

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