Castiglione del Bosco Holiday Rentals, Montalcino: Private House Rentals

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

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

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

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

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

฿41,654

฿46,196 total

includes taxes & fees

3 Nov - 4 Nov

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

Farasley

฿3,183

฿4,368 total

includes taxes & fees

29 Oct - 30 Oct

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

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.

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

3. Villa Le Prata - Residenza del Vescovo

Montalcino

Karen

฿14,423

฿16,242 total

includes taxes & fees

5 Nov - 6 Nov

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 wooden deck and white lounge chairs.

4. Podere Brizio

Montalcino

Aseem

฿6,731

฿7,706 total

includes taxes & fees

16 Nov - 17 Nov

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 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.

5. Casa Franci Montalcino

Montalcino

Jim

฿7,070

฿8,155 total

includes taxes & fees

16 Nov - 17 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.

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.

6. Capanna Suites

Montalcino

Randy

฿10,886

฿12,351 total

includes taxes & fees

26 Oct - 27 Oct

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.

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.

7. Le Ragnaie

Montalcino

Trevor

฿3,324

฿4,033 total

includes taxes & fees

28 Oct - 29 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 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."

8. Hotel Dei Capitani

Montalcino

Phillip

฿4,508

฿5,260 total

includes taxes & fees

28 Oct - 29 Oct

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.

9. Hotel Ghibellino

Buonconvento

Anna-Maree

฿3,089

฿3,511 total

includes taxes & fees

28 Oct - 29 Oct

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.

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

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

10. Mercure Petriolo Siena Terme Spa Hotel

Civitella Paganico

Penny

฿2,824

฿3,182 total

includes taxes & fees

27 Oct - 28 Oct

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

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

A courtyard with outdoor seating, a building with multiple windows, and a stone wall.

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

11. Palazzo Saloni

Montalcino

Michael

฿8,753

฿10,005 total

includes taxes & fees

2 Nov - 3 Nov

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

A courtyard with a stone wall, a small pond, and a waterfall. There are trees and plants around, and a building in the background.

12. Albergo Giardino

Montalcino

Norma

฿4,005

฿4,707 total

includes taxes & fees

5 Nov - 6 Nov

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

A picnic setup with a basket, blanket, pillows, and food items on a grassy area with a hilly landscape in the background.

13. Mastrojanni Relais - Small Luxury Hotels of the World

Montalcino

Gurnek

฿14,845

฿16,706 total

includes taxes & fees

7 Nov - 8 Nov

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

An outdoor courtyard with a fire pit, seating area, and a large tree providing shade.

A bedroom with a large bed, a wardrobe, a chair, and a ceiling with exposed beams.

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

14. Palazzo Lucchini

Montalcino

฿13,283

฿14,988 total

includes taxes & fees

22 Oct - 23 Oct

A clear pool with a stone wall and a wooden bridge.

A narrow cobblestone street with a restaurant named "Trattoria al Vecchio Forno" and a sign indicating "Giardino" (garden).

A stone-walled room with a large bathtub, a fireplace, and a set of stone steps leading to the tub.

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

15. Hotel Palazzo del Capitano Wellness & Relais - Luxury Borgo Capitano Collection

San Quirico d'Orcia

Edward

฿6,020

฿6,810 total

includes taxes & fees

22 Oct - 23 Oct

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

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

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

An outdoor patio with stone walls, a pergola, and a table set for dining.

16. Dimora delle Muse

Montalcino

Bradley N.

฿5,903

฿6,794 total

includes taxes & fees

2 Nov - 3 Nov

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

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

17. Hotel Borgo Antico

Monteroni d'Arbia

Charles

฿3,252

฿3,766 total

includes taxes & fees

26 Oct - 27 Oct

A stone building with a pool overlooking a mountainous landscape.

A stone pathway leading to a gate with tall cypress trees on either side, illuminated by soft lighting.

A terrace with stone walls, potted plants, and outdoor furniture overlooking a valley with a river and distant hills during sunset.

18. Castello di Velona Resort Thermal SPA & Winery

Montalcino

Melanie

฿19,049

฿21,332 total

includes taxes & fees

15 Nov - 16 Nov

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

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

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

A large stone castle with multiple towers, surrounded by vineyards and cypress trees.

19. Castello Banfi - Il Borgo - Relais et Chateaux

Montalcino

Jason

฿37,313

฿41,421 total

includes taxes & fees

30 Oct - 31 Oct

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

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

20. L'Orto delle Terme

San Quirico d'Orcia

Tracey

฿4,262

฿4,839 total

includes taxes & fees

8 Nov - 9 Nov

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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? 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

"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."

Il Chiostro del Carmine

8/10 Good

"We really enjoyed our stay at Il Chiostro del Carmine. The hotel is definitely a little older, but that was part of the charm for us. Staying inside a former monastery gave the property so much character and made it feel completely different from a typical hotel. The location was also excellent. It sits just outside the busiest part of Siena, but we were still within about a 10-minute walk of pretty much everything we wanted to see or do. The atmosphere was peaceful, the setting was unique, and it fit Siena perfectly. If you prefer hotels with history and character over ultra-modern ones, this is a great place to stay."

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"

Piccolo Hotel Etruria

10/10 Excellent

"This is a clean and charming hotel very centrally located in Siena. The morning and afternoon staff were very helpful. We will definitely stay at the Piccolo Hotel Etruria on our next visit. We will also recommend it to friends."

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."

Four Points by Sheraton Siena

8/10 Good

"Property seem reasonable, staff helpful, rooms are little small and dated, bathrooms need renovation."

More cheap stays in Castiglione del Bosco

Cannon d'Oro

Via Montanini 28 Siena SI

฿1,801

฿2,094 total

21 Nov - 22 Nov

includes taxes & fees

7.8/10 Good! (259 reviews)

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI

฿2,551

฿2,919 total

6 Nov - 7 Nov

includes taxes & fees

7.8/10 Good! (453 reviews)

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI

฿2,911

฿3,316 total

3 Nov - 4 Nov

includes taxes & fees

8.8/10 Excellent! (114 reviews)

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI

฿2,962

฿3,372 total

16 Nov - 17 Nov

includes taxes & fees

10/10 Exceptional! (52 reviews)

Hotel La Terrazza di Montepulciano

Via Pié al Sasso 16 Montepulciano SI

฿3,766

฿4,293 total

22 Oct - 23 Oct

includes taxes & fees

9.4/10 Exceptional! (217 reviews)

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI

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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 traveller data. This hotel offers a winery and 2 outdoor pools. Other good options for your trip to the area are Hotel Athena and Grand Hotel Continental Siena – Starhotels Collezione. See all available top hotels, or vacation rentals in Castiglione del Bosco.

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

Yes! Most room reservations are fully refundable as long as you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your arrival date. If you have a reservation that's non-refundable, you might still have the option to cancel and get a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Castiglione del Bosco.

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

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

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 3395 hotels and other accommodation options in the surrounding area. Find out more about Castiglione del Bosco.

What should I do while I'm visiting Castiglione del Bosco?

A favourite place to visit is Castiglion del Bosco Winery. You'll also find Fortress of Montalcino and Tenuta Greppo Franco Biondi Santi in the area. Take a look at what more there is 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 temperature of 22°C, while the coldest months are January and February, with an average of 6°C. Average annual precipitation for Castiglione del Bosco is 944 mm.

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Find hotels in Castiglione del Bosco from ฿2,094

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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Star rating

Guest rating

Our top choices for Castiglione del Bosco hotels

1. Castiglion del Bosco, A Rosewood Hotel

2. SI Montalcino Hotel

3. Villa Le Prata - Residenza del Vescovo

4. Podere Brizio

5. Casa Franci Montalcino

6. Capanna Suites

7. Le Ragnaie

8. Hotel Dei Capitani

9. Hotel Ghibellino

10. Mercure Petriolo Siena Terme Spa Hotel

11. Palazzo Saloni

12. Albergo Giardino

13. Mastrojanni Relais - Small Luxury Hotels of the World

14. Palazzo Lucchini

15. Hotel Palazzo del Capitano Wellness & Relais - Luxury Borgo Capitano Collection

16. Dimora delle Muse

17. Hotel Borgo Antico

18. Castello di Velona Resort Thermal SPA & Winery

19. Castello Banfi - Il Borgo - Relais et Chateaux

20. L'Orto delle Terme

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

Villa Ermellina Siena, a Tribute Portfolio Hotel

Il Chiostro del Carmine

Castello di Velona Resort Thermal SPA & Winery

Hotel San Gregorio

Piccolo Hotel Etruria

L'Orto delle Terme

Hotel Chiusarelli

Four Points by Sheraton Siena

More cheap stays 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

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