Castiglione del Bosco Hotel & Accommodation Deals 2026 from AU$87 - Compare prices by date

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Castiglione del Bosco

Pet friendly

Villa

Apartment

Spa

Condo

Apart hotel

Pool

Spa pool

Farm

Family friendly

Waterpark

Check prices for these dates

Tonight

Tomorrow

Next weekend

In two weeks

Our top choices for Castiglione del Bosco hotels

An infinity pool with lounge chairs and umbrellas, surrounded by a forested hillside.

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

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

A rural landscape with a stone house, a swimming pool, and rolling hills in the background.

1. Castiglion del Bosco, A Rosewood Hotel

Montalcino

Mohammed

AU$2,002

includes taxes & fees

4 Nov - 5 Nov

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

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.

2. Hotel Ghibellino

Buonconvento

Anna-Maree

AU$146

includes taxes & fees

26 Oct - 27 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 kitchen with a buffet setup, including a variety of food items and glassware.

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

3. SI Montalcino Hotel

Montalcino

Farasley

AU$175

includes taxes & fees

3 Nov - 4 Nov

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

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.

A bedroom with a large bed, wooden beams on the ceiling, a nightstand with a lamp, and framed pictures on the wall.

4. Le Ragnaie

Montalcino

Trevor

AU$163

includes taxes & fees

10 Nov - 11 Nov

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

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

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.

5. Podere Brizio

Montalcino

Aseem

AU$319

includes taxes & fees

16 Nov - 17 Nov

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

6. Mercure Petriolo Siena Terme Spa Hotel

Civitella Paganico

Mike

AU$135

includes taxes & fees

28 Oct - 29 Oct

A room with a view of a vineyard, a table with cups and saucers, and a window with curtains.

A vineyard with terraced fields and a stone building with a sloped roof.

An aerial view of a stone house with a driveway, a covered outdoor area, and a well-lit landscape at dusk.

A bedroom with a bed, a nightstand, a lamp, and a window with a view of a vineyard and trees.

7. Wine Estate Paradiso di Cacuci

Montalcino

Tony

AU$429

includes taxes & fees

27 Oct - 28 Oct

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

8. Hotel Dei Capitani

Montalcino

Phillip

AU$208

includes taxes & fees

28 Oct - 29 Oct

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

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.

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

9. Casa Franci Montalcino

Montalcino

Jim

AU$377

includes taxes & fees

16 Nov - 17 Nov

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.

10. Villa Le Prata - Residenza del Vescovo

Montalcino

Karen

AU$700

includes taxes & fees

7 Nov - 8 Nov

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 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.

11. Palazzo Saloni

Montalcino

Michael

AU$450

includes taxes & fees

24 Nov - 25 Nov

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

12. Capanna Suites

Montalcino

Randy

AU$522

includes taxes & fees

21 Nov - 22 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.

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

An underground wine cellar with wooden tables, wine bottles, and a piano.

13. Dimora delle Muse

Montalcino

Bradley N.

AU$287

includes taxes & fees

7 Nov - 8 Nov

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

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

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

A rustic interior with stone walls, a large ornate mirror, a blue sofa, and a wooden coffee table.

14. Albergo Giardino

Montalcino

Norma

AU$199

includes taxes & fees

16 Nov - 17 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 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 historic building with a sign reading "Borgo Antico" and a "Ristorante" sign below.

15. Hotel Borgo Antico

Monteroni d'Arbia

Charles

AU$143

includes taxes & fees

26 Oct - 27 Oct

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

An aerial view of a town with a central square, a swimming pool, and surrounding residential buildings.

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.

16. Palazzuolo

San Quirico d'Orcia

Alberto

AU$189

includes taxes & fees

29 Oct - 30 Oct

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.

17. Fattoria Pieve a Salti

Montalcino

Marko

AU$184

includes taxes & fees

10 Nov - 11 Nov

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 couple in a hot tub with water jets, surrounded by a wooden wall and a blurred background.

18. L'Orto delle Terme

San Quirico d'Orcia

Tracey

AU$199

includes taxes & fees

24 Nov - 25 Nov

A modern bedroom with a large bed, a desk, and a mirror.

A room with a blue sofa, a small table with a lamp, and a chair.

A room with a central island, a painting on the wall, and a potted plant.

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

19. Palazzo Lucchini

Montalcino

AU$634

includes taxes & fees

4 Nov - 5 Nov

Two people sitting at a round table outdoors with a scenic view of mountains in the background.

A breakfast buffet with various food items and beverages.

A bar area with a wooden bar counter, three orange chairs, and a variety of bottles and glasses.

A patio area with wicker furniture, a glass table, and a pool in the background.

20. Hotel Corsignano

Pienza

Tatiana

AU$213

includes taxes & fees

12 Nov - 13 Nov

View all properties

Save an average of 15% on thousands of hotels when you're signed in

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? 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

Recent Reviews in Castiglione del Bosco

NH Siena

10/10 Excellent

"The room isn't cleaned too well. There were some crumbs that were attracting ants. Other than that- no issues"

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent

"Stayed at the hotel for our honeymoon and it was an incredible experience. The view is simply breathtaking and the castle is extremely charming. Food (breakfast and diner) and wine at the restaurants are high quality, inspired and locally sourced, though expensive. Their Brunello is VERY good. The thermal spa experience is unique in the region and is awsome, especially during the fall season when it is cooler outside. The room was super clean and the staff was very helpful throughout the entire week, and we felt welcomed at any time of day. 15 min by car from Montalcino, strongly recommend to rent a car since it is slightly remote. Overall 9.5/10, strongly recommend for a special occasion."

Castiglion del Bosco, A Rosewood Hotel

10/10 Excellent

"Fabulous service. Gorgeous location and pristine hotel. Great food choices and services."

Grand Hotel Continental Siena – Starhotels Collezione

8/10 Good

"Excellent location. Very nice service."

Hotel Minerva

10/10 Excellent

"The check-in staff were very friendly, helpful, and spoke English. The €20 parking in their garage was very nice and convenient, especially when it rained. Nice view from the room."

Il Chiostro del Carmine

8/10 Good

"Breakfast"

Castello di Leonina Relais

10/10 Excellent

"Beautiful place, great food, easy to access location! Loved our stay!"

Hotel Italia

10/10 Excellent

"We stayed at this basic but nice 3-star hotel just one night while visiting Siena. We had a room for 3 for my wife and I and our adult daughter. The hotel was easy walking distance from the train/bus station. It's kind of weird because you enter an indoor shopping area across the street from the station and then go up about 6 banks of escalators to get up the hillside. Then the hotel is just a block away. One of the AC units didn't work but friendly staff helped start the other one. All staff were very friendly and spoke English. Easy walk a few blocks into the old city. Wonderful breakfast!!! We were able to leave our bags for most of the day while we explored the city prior to leaving on the bus again. I would definitely stay again."

Villa Ermellina Siena, a Tribute Portfolio Hotel

8/10 Good

"We were in one of the other wings so it wasn't in the main building. It was a rainy week and we had a wedding and there were no rooms in the main building to accommodate us. There is no overhead so you will get wet and there are a million stairs to get to that wing (you will need help if you have a ton of luggage as well). The hotel is far from city center too, you need to plan your cabs out accordingly."

More cheap accommodation in Castiglione del Bosco

Cannon d'Oro

Via Montanini 28 Siena SI

AU$88

21 Nov - 22 Nov

includes taxes & fees

7.8/10 Good! (259 reviews)

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI

AU$116

24 Nov - 25 Nov

includes taxes & fees

7.8/10 Good! (453 reviews)

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI

AU$127

2 Nov - 3 Nov

includes taxes & fees

8.8/10 Excellent! (114 reviews)

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI

AU$142

16 Nov - 17 Nov

includes taxes & fees

10/10 Exceptional! (52 reviews)

Hotel La Terrazza di Montepulciano

Via Pié al Sasso 16 Montepulciano SI

AU$182

26 Oct - 27 Oct

includes taxes & fees

9.4/10 Exceptional! (218 reviews)

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI

Get rates

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 cancelled 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 can I save on a hotel booking in Castiglione del Bosco with Expedia?

One Key™—Expedia's free travel rewards program—gives you instant access to discounts with Member Prices on Castiglione del Bosco hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

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

Prices for hotels in Castiglione del Bosco often vary, but you can find a great deal from AU$87 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 our cheapest rates.

Explore a world of travel with Expedia

Siena Holiday Rentals

Activities in Rosia

Book Hotels in Castiglione del Bosco on Expedia.it

Search Castiglione del Bosco hotels

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Castiglione del Bosco

Check prices for these dates

Filter by

Property class

Guest rating

Our top choices for Castiglione del Bosco hotels

1. Castiglion del Bosco, A Rosewood Hotel

2. Hotel Ghibellino

3. SI Montalcino Hotel

4. Le Ragnaie

5. Podere Brizio

6. Mercure Petriolo Siena Terme Spa Hotel

7. Wine Estate Paradiso di Cacuci

8. Hotel Dei Capitani

9. Casa Franci Montalcino

10. Villa Le Prata - Residenza del Vescovo

11. Palazzo Saloni

12. Capanna Suites

13. Dimora delle Muse

14. Albergo Giardino

15. Hotel Borgo Antico

16. Palazzuolo

17. Fattoria Pieve a Salti

18. L'Orto delle Terme

19. Palazzo Lucchini

20. Hotel Corsignano

Stay near popular Castiglione del Bosco attractions

Castiglion del Bosco Winery

Learn more about Castiglione del Bosco

Top Castiglione del Bosco Hotel Reviews

Recent Reviews in Castiglione del Bosco

NH Siena

Castello di Velona Resort Thermal SPA & Winery

Castiglion del Bosco, A Rosewood Hotel

Grand Hotel Continental Siena – Starhotels Collezione

Hotel Minerva

Il Chiostro del Carmine

Castello di Leonina Relais

Hotel Italia

Villa Ermellina Siena, a Tribute Portfolio Hotel

More cheap accommodation in Castiglione del Bosco

Cannon d'Oro

Piccolo Hotel Etruria

Albergo Centrale

Torre del Fuggisole

Hotel La Terrazza di Montepulciano

Porta Pispini Residence

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app