Book The Best Hotels in Castiglione del Bosco for 2026 from CA $98 - 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 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.

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

CA $2,617

CA $2,895 total

includes taxes & fees

Oct 30 - Oct 31

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

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.

2. SI Montalcino Hotel

Montalcino

Sam

CA $126

CA $175 total

includes taxes & fees

Oct 30 - Oct 31

A breakfast table with croissants, a pitcher, a teapot, and a vase with flowers.

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

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

3. Hotel Ghibellino

Buonconvento

Anna-Maree

CA $122

CA $139 total

includes taxes & fees

Oct 21 - Oct 22

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 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.

4. Podere Brizio

Montalcino

Aseem

CA $271

CA $311 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 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.

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

5. Hotel Dei Capitani

Montalcino

Phillip

CA $171

CA $201 total

includes taxes & fees

Oct 6 - Oct 7

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 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.

6. Le Ragnaie

Montalcino

Trevor

CA $135

CA $165 total

includes taxes & fees

Nov 3 - Nov 4

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.

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

7. Capanna Suites

Montalcino

Michael

CA $414

CA $471 total

includes taxes & fees

Oct 28 - Oct 29

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

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

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.

8. Mercure Petriolo Siena Terme Spa Hotel

Civitella Paganico

Mike

CA $120

CA $132 total

includes taxes & fees

Oct 4 - Oct 5

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 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.

9. Casa Franci Montalcino

Montalcino

Peter

CA $273

CA $317 total

includes taxes & fees

Oct 6 - Oct 7

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 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

CA $222

CA $257 total

includes taxes & fees

Oct 4 - Oct 5

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.

11. Albergo Giardino

Montalcino

Norma

CA $170

CA $200 total

includes taxes & fees

Nov 2 - Nov 3

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 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.

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

12. Hotel Borgo Antico

Monteroni d'Arbia

Charles

CA $134

CA $156 total

includes taxes & fees

Oct 31 - Nov 1

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

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

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.

13. Dimora delle Muse

Montalcino

Bradley N.

CA $259

CA $298 total

includes taxes & fees

Nov 2 - Nov 3

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.

14. Fattoria Pieve a Salti

Montalcino

Marko

CA $169

CA $192 total

includes taxes & fees

Oct 4 - Oct 5

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

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.

A brick building with two windows and wooden shutters, surrounded by greenery.

15. L'Aia di Argia

Monteroni d'Arbia

mario

CA $103

CA $119 total

includes taxes & fees

Oct 4 - Oct 5

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

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

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

A room with a sofa, a checkered rug, a mirror on the wall, and a door leading to another room.

16. Palazzo Lucchini

Montalcino

CA $547

CA $617 total

includes taxes & fees

Oct 9 - Oct 10

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

17. Palazzo Saloni

Montalcino

Michael

CA $315

CA $363 total

includes taxes & fees

Nov 2 - Nov 3

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.

18. L'Orto delle Terme

San Quirico d'Orcia

Stimson

CA $181

CA $206 total

includes taxes & fees

Oct 15 - Oct 16

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 stone building with a gravel pathway leading to the entrance.

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

19. Agriturismo Il Macchione

Pienza

YOUNG BAE

CA $268

CA $301 total

includes taxes & fees

Nov 2 - Nov 3

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

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

20. Villa Le Prata - Residenza del Vescovo

Montalcino

Karen

CA $733

CA $823 total

includes taxes & fees

Nov 1 - Nov 2

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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

Villa Scacciapensieri Boutique Hotel

10/10 Excellent

"This hotel was PERFECT for our honeymoon trip to Siena. It was peaceful and quiet, but still close enough to get to the city centre and the train station easily. The pool was a perfect oasis after hot days. The staff were so friendly and helpful. The terrace was a gorgeous place for a night cap at the end of the night. We would definitely stay here again."

Il Chiostro del Carmine

10/10 Excellent

"Room clean large spacious staff friendly helpful good quiet location great views"

Castiglion del Bosco, A Rosewood Hotel

10/10 Excellent

"Castiglion del Bosco is truly exquisite, the perfect way to experience Tuscany in luxury while still feeling completely surrounded by nature. The property is impeccable, from the beautiful gardens and grounds to the elegant rooms. Everything feels authentically Italian, refined and incredibly well maintained. The service is exceptional and very personalized. The staff genuinely goes out of their way to make you feel welcome. General Manager Nicola Migheli even greeted us personally upon arrival, which was a lovely touch. We also saw him regularly walking the property with his team, and it was clear how hands-on he is with every detail. One thing to know is that getting in and out requires about 40 minutes on a bumpy dirt road. It wasn’t terrible, but worth mentioning if you plan to explore frequently. That said, this is a hotel you don’t need to leave. It’s a beautiful place to slow down, relax and enjoy Tuscany in a truly special setting. We absolutely loved our stay!"

Albergo Le Terme

10/10 Excellent

"It was amazing."

Hotel Athena

10/10 Excellent

"The hotel is wonderful! The staff is extremely friendly and helpful. The location is great…jut a short walk to shopping, restaurants, and the cathedral. Our room was very clean and the beds were comfortable. The view from the terrace is stunning."

Hotel Minerva

10/10 Excellent

"If you are driving in Italy this is the best place to stay. Easy in and out with on site parking, zero stress! Easy walk into the heart of Siena. The staff were wonderful and the rooms clean."

Four Points by Sheraton Siena

10/10 Excellent

"Excellent property. It was well maintained, and the staff was friendly. I would definitely stay here again."

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent

"Concierge staff is fantastic. Bar staff as well. Location can’t be beat. Ground zero for Siena activity."

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 $82

CA $98 total

Oct 28 - Oct 29

includes taxes & fees

7.8/10 Good! (258 reviews)

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI

CA $132

CA $150 total

Nov 3 - Nov 4

includes taxes & fees

8.8/10 Excellent! (108 reviews)

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI

CA $132

CA $150 total

Nov 3 - Nov 4

includes taxes & fees

10/10 Exceptional! (50 reviews)

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI

CA $157

CA $181 total

Oct 4 - Oct 5

includes taxes & fees

7.8/10 Good! (445 reviews)

Hotel La Terrazza di Montepulciano

Via Pié al Sasso 16 Montepulciano SI

CA $160

CA $182 total

Oct 6 - Oct 7

includes taxes & fees

9.4/10 Exceptional! (211 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 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 $98 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 CA $98

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. Hotel Ghibellino

4. Podere Brizio

5. Hotel Dei Capitani

6. Le Ragnaie

7. Capanna Suites

8. Mercure Petriolo Siena Terme Spa Hotel

9. Casa Franci Montalcino

10. Hotel Vecchia Oliviera

11. Albergo Giardino

12. Hotel Borgo Antico

13. Dimora delle Muse

14. Fattoria Pieve a Salti

15. L'Aia di Argia

16. Palazzo Lucchini

17. Palazzo Saloni

18. L'Orto delle Terme

19. Agriturismo Il Macchione

20. Villa Le Prata - Residenza del Vescovo

Stay near popular Castiglione del Bosco attractions

Castiglion del Bosco Winery

Learn more about Castiglione del Bosco

Top Castiglione del Bosco Hotel Reviews

Villa Scacciapensieri Boutique Hotel

Il Chiostro del Carmine

Castiglion del Bosco, A Rosewood Hotel

Albergo Le Terme

Hotel Athena

Hotel Minerva

Four Points by Sheraton Siena

Grand Hotel Continental Siena – Starhotels Collezione

Castello di Velona Resort Thermal SPA & Winery

More cheap stays in Castiglione del Bosco

Cannon d'Oro

Albergo Centrale

Torre del Fuggisole

Piccolo Hotel Etruria

Hotel La Terrazza di Montepulciano

Porta Pispini Residence

Frequently asked questions

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