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Jun 5 - Jun 7
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Jun 12 - Jun 14

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Our top choices for Castiglione del Bosco hotels

Villa (Agresto) | Living area

Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel
5.0 star property
Montalcino
10.0 out of 10, Exceptional, (77 reviews)
"Everything was perfect "
United States
Ralip
The price is CA $3,053
CA $3,374 total
includes taxes & fees
Jun 7 - Jun 8
Castiglion del Bosco, A Rosewood Hotel
Seasonal outdoor pool, open 9:30 AM to 7:00 PM, pool umbrellas

SI Montalcino Hotel

SI Montalcino Hotel
3.0 star property
Montalcino
9.2 out of 10, Wonderful, (386 reviews)
"The staff were friendly and very helpful & accommodating. The beds were comfortable and the breakfast was abundant and good options. A great place to stay."
United States
Mark
The price is CA $184
CA $215 total
includes taxes & fees
Jun 17 - Jun 18
SI Montalcino Hotel
Hiking

Borgo Sant'Ambrogio Resort

Borgo Sant'Ambrogio Resort
5.0 star property
Trequanda
9.6 out of 10, Exceptional, (111 reviews)
"The location is sublime and the facility is AMAZING"
United States
Steven
The price is CA $260
CA $291 total
includes taxes & fees
Jun 26 - Jun 27
Borgo Sant'Ambrogio Resort
Property grounds

Poggio Paradiso Resort & Spa

Poggio Paradiso Resort & Spa
Torrita di Siena
10.0 out of 10, Exceptional, (22 reviews)
"Excellent room and food. Great location!"
United States
Saurabh
The price is CA $428
CA $480 total
includes taxes & fees
Jun 16 - Jun 17
Poggio Paradiso Resort & Spa
Garden

Palace Hotel Due Ponti

Palace Hotel Due Ponti
3.0 star property
Due Ponti
8.4 out of 10, Very good, (59 reviews)
"Breakfast was good. Refrigerator did not work in room but staff allowed us to use a other fridge."
Canada
Gregory
The price is CA $117
CA $137 total
includes taxes & fees
Jun 27 - Jun 28
Palace Hotel Due Ponti
Deluxe Double Room, 1 King Bed, Non Smoking

Dimora delle Muse

Dimora delle Muse
Montalcino
10.0 out of 10, Exceptional, (68 reviews)
"The breakfast was great. Sara and Michele are great hosts and have great recommendations for their guests. Very good place to stay. "
United States
Bradley N.
The price is CA $296
CA $338 total
includes taxes & fees
Jun 22 - Jun 23
Dimora delle Muse
Indoor pool, open 9:00 AM to midnight, sun loungers

Albergo San Biagio

Albergo San Biagio
3.0 star property
Montepulciano
8.8 out of 10, Excellent, (218 reviews)
"Excellent stay!"
United States
Rodolfo
The price is CA $102
CA $118 total
includes taxes & fees
Jun 7 - Jun 8
Albergo San Biagio
Exterior

Le Ragnaie

Le Ragnaie
Montalcino
9.2 out of 10, Wonderful, (326 reviews)
"Great place to stay the staff was super friendly and very close to Monalcino. Good wine everywhere. The scenery was so beautiful! "
United States
Douglas
The price is CA $233
CA $273 total
includes taxes & fees
Jun 16 - Jun 17
Le Ragnaie
Front of property

Podere Brizio

Podere Brizio
Montalcino
9.8 out of 10, Exceptional, (159 reviews)
"Stunning location & great reception from Vito. He looked after us & gave us some great recommendations for a wine tasting day out. The accommodation & views were beautiful. We also loved using the spa facilities & played tennis a couple of times overlooking the vineyard! Breakfast was great & dinner in the restaurant was amazing. A great stay & highly recommend! "
United Kingdom
karen
The price is CA $303
CA $347 total
includes taxes & fees
Jun 7 - Jun 8
Podere Brizio
Lunch and dinner served

Locanda In Tuscany

Locanda In Tuscany
Castiglione d'Orcia
9.8 out of 10, Exceptional, (21 reviews)
"Our stay at Locanda in Tuscany was nothing short of spectacular. Nestled in the heart of the Tuscan countryside, the hotel offers breathtaking views that capture the essence of this picturesque region. The staff were exceptional, anticipating our needs and promptly responding to all our requests, from arranging wine tastings to making dining reservations. The rooms were beautifully appointed with luxurious amenities that blended seamlessly with the rustic charm of the surroundings. Our daughter...
India
Shashidhar
The price is CA $369
CA $412 total
includes taxes & fees
Jun 22 - Jun 23
Locanda In Tuscany
Front of property

L'Orto delle Terme

L'Orto delle Terme
San Quirico d'Orcia
9.6 out of 10, Exceptional, (43 reviews)
"Lovely stay"
United States
Stimson
The price is CA $182
CA $207 total
includes taxes & fees
Jun 29 - Jun 30
L'Orto delle Terme
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

Capanna Suites

Capanna Suites
Montalcino
9.8 out of 10, Exceptional, (137 reviews)
"Excellent hotel, very beautiful, peaceful and serene. Rooms are gorgeous and spacious. Food and service is incredible. Felt very high end and relaxing the whole time! "
United States
Andrew
The price is CA $544
CA $614 total
includes taxes & fees
Jun 21 - Jun 22
Capanna Suites
Lobby sitting area

Tenuta Santo Pietro

Tenuta Santo Pietro
Pienza
9.6 out of 10, Exceptional, (123 reviews)
"Beautiful villa! Everything was so cozy and inviting. The staff was very attentive and friendly- they went out of their way to accommodate us for breakfast since we were exhausted and slept in. Food was incredible, chef made and always served with a smile and light conversation. 100% would recommend and would love to return in the future ! Location was perfect as well and made trips to nearby towns/ sightseeing a breeze!!!"
United States
Jamie
The price is CA $405
CA $452 total
includes taxes & fees
Jun 30 - Jul 1
Tenuta Santo Pietro
Balcony view

Hotel La Terrazza di Montepulciano

Hotel La Terrazza di Montepulciano
2.0 star property
Montepulciano
9.2 out of 10, Wonderful, (206 reviews)
"Very clean and the owner was very delightful "
Canada
Chad
The price is CA $161
CA $183 total
includes taxes & fees
Jun 16 - Jun 17
Hotel La Terrazza di Montepulciano
Hiking

Palazzo Brandano

Palazzo Brandano
Trequanda
9.6 out of 10, Exceptional, (88 reviews)
"A beautiful place! Breathtaking "
United States
Anabel
The price is CA $186
CA $209 total
includes taxes & fees
Jun 14 - Jun 15
Palazzo Brandano
Exterior

Hotel Vecchia Oliviera

Hotel Vecchia Oliviera
3.0 star property
Montalcino
9.4 out of 10, Exceptional, (67 reviews)
"Perfect location and wonderful staff!"
United States
Laura
The price is CA $182
CA $219 total
includes taxes & fees
Jun 6 - Jun 7
Hotel Vecchia Oliviera
Breakfast, lunch, dinner and brunch served

Castello di Leonina Relais

Castello di Leonina Relais
4.0 star property
Asciano
9.0 out of 10, Wonderful, (130 reviews)
"We had a wonderful stay. The place was immaculate, beautifully maintained, and truly one of our favorite accommodations in Italy. Although it was a bit farther from Montepulciano, Pienza, and Montalcino, it was absolutely worth the drive. Its proximity to Siena made it a perfect base, and we genuinely enjoyed every moment of our stay."
Canada
Raphaelle
The price is CA $272
CA $308 total
includes taxes & fees
Jun 18 - Jun 19
Castello di Leonina Relais
Indoor pool, seasonal outdoor pool

Mercure Petriolo Siena Terme Spa Hotel

Mercure Petriolo Siena Terme Spa Hotel
5.0 star property
Civitella Paganico
8.6 out of 10, Excellent, (248 reviews)
"We had a great time. I would recommend this hotel when in Tuscany. "
United States
Mike
The price is CA $128
CA $141 total
includes taxes & fees
Jun 18 - Jun 19
Mercure Petriolo Siena Terme Spa Hotel
Outdoor dining

Palazzo di Valli

Palazzo di Valli
3.0 star property
Siena
9.6 out of 10, Exceptional, (423 reviews)
"We had a great stay. Fantastic panoramic views. Very comfortable room. Super friendly host!"
United States
Yuliya
The price is CA $273
CA $308 total
includes taxes & fees
Jun 27 - Jun 28
Palazzo di Valli
Spa

Mastrojanni Relais - Small Luxury Hotels of the World

Mastrojanni Relais - Small Luxury Hotels of the World
Montalcino
10.0 out of 10, Exceptional, (69 reviews)
"Wonderfully Beautiful Winery… Stunning views. Fabulous rooms and very welcoming staff."
United States
Laura
The price is CA $840
CA $940 total
includes taxes & fees
Jun 13 - Jun 14
Mastrojanni Relais - Small Luxury Hotels of the World
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Stay near popular Castiglione del Bosco attractions

Castiglion del Bosco Winery

4.8/5 (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
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Open Photo by tom owens

Top Castiglione del Bosco Hotel Reviews

Borgo Santo Pietro

Borgo Santo Pietro

2/10 Terrible
"While the property itself is beautiful, our overall experience was extremely disappointing and fell far below the standard we expected. From the moment we arrived, we encountered multiple issues that were handled poorly by management and staff. Our initial room had no functioning air conditioning, making it uncomfortable and unusable. We were initially told the hotel was fully booked, yet we were eventually moved to another room after considerable discussion. This was particularly frustrating given that we had even offered to pay for an upgraded room. The most disappointing aspect of our stay was the way my wife was treated. When she respectfully raised concerns regarding several issues we experienced, members of the staff responded dismissively and, at times, appeared to laugh at her concerns rather than address them professionally. No guest should ever be made to feel ignored or ridiculed when raising legitimate issues. To make matters worse, hotel staff damaged my wife’s luggage during our stay. Management acknowledged the issue and repeatedly assured us that they would resolve it and make things right. However, after we checked out, those assurances turned into delays, excuses, and ultimately a complete lack of communication. Despite multiple commitments to address the matter, management stopped responding altogether. We booked this property expecting a memorable and exceptional experience for a special occasion. Unfortunately, it was terrible and staff underwhelming."
Nicholas 2-night trip
Posted 1 hour ago
Borgo Santo Pietro

More cheap stays in Castiglione del Bosco

Cannon d'Oro

Cannon d'Oro

Via Montanini 28 Siena SI
The price is CA $132 per night from Jun 24 to Jun 25
CA $132
CA $153 total
Jun 24 - Jun 25
includes taxes & fees
7.8/10 Good! (257 reviews)

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 can I save on a Castiglione del Bosco hotel booking with Expedia?
Members always get our best prices. Find our best Castiglione del Bosco hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
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 $153 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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