How do we rate a property?
We rate all our hotels, resorts, and lodges using our own bespoke grading system. We'll only invite a property into our collection once it's been assessed by one of our specialists. If it doesn't impress us, it doesn't make the cut.
From the quality of the food served in the restaurant to the amenities offered in each bedroom, we carefully rate each property to make sure it meets our high expectations.
More about how we rate our propertiesRosewood Castiglion del Bosco
How do we rate a property?
We rate all our hotels, resorts, and lodges using our own bespoke grading system. We'll only invite a property into our collection once it's been assessed by one of our specialists. If it doesn't impress us, it doesn't make the cut.
From the quality of the food served in the restaurant to the amenities offered in each bedroom, we carefully rate each property to make sure it meets our high expectations.
More about how we rate our propertiesKiwi Collection Rate
Location
Located in Tuscany’s Brunello wine region, Rosewood Castiglion del Bosco is 20 minutes northwest of Montalcino, in the Province of Siena.
About This Hotel
Standing at the top of a rolling hill, guests watch the sun hazily creep up over the countless rows of vines. Much like the wine produced in Tuscany, the scenery of Rosewood Castiglion del Bosco is intoxicating, and demands to be savored.
Tuscany is lush, seductive, and by all counts, addictive. The sprawling estate of Rosewood Castiglion del Bosco’ wine-producing lands date back nearly 800 years.
The heart of the estate is Il Borgo, made up of 23 restored 17th - and 18th-century suites, plus Il Canonica (a cooking school, two restaurants serving local produce, meats and the freshest of pastas, and a cigar and cognac lounge), an Italian Kitchen Garden, Infinity pool, and A Care Suite Spa by Daniel Steiner.
The vine-strewn grounds produce their sacred juices, and feed the award-winning winery that shares the hotel's namesake. Originally for private use, the winery only became commercial on 1950, and now produces a grouping of acclaimed Brunellos.
Aside from the winery itself, the grounds also feature the Drago Golf Course, designed by Tom Weiskopf. And that's just the beginning. Extensive hiking and biking trails pass over ridges, and by streams and waterfalls. Go old school, and follow the lead of Tuscan herdsman riding magnificent Maremma horses — you'll need to work up an appetite to truly sample all the flavors of Tuscany.
Hotel Amenities
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Pet friendly
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Wi-Fi Internet
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Restaurant(s)
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Gym
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Spa
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Private pools
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Tennis court(s)
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Flat Screen TV
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iPod dock in rooms
Room Options
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Deluxe Room
*Actual room may differ from image shown
The Deluxe Rooms are very spacious, with master bedroom with bathroom and c... Read More
Deluxe Room
*Actual room may differ from image shown
The Deluxe Rooms are very spacious, with master bedroom with bathroom and comfortable sitting corner. Some of these rooms also have a private terrace overlooking the Tuscan hills. They’re characterized by warm colours, welcoming atmospheres and are all located in main buildings of the “Borgo”. These rooms size ranges from 49 to 51 sq. mt. / 527 to 559 sq. ft. EXTRA BED: not allowed - maximum occupancy is 2 persons. BABY Crib free of charge: for babies up to 2 years old.
Room size: 50 m2 / 538 ft2
Room size: 50 m2 / 538 ft2
The Deluxe Rooms are very spacious, with master bedroom with bathroom and comfortable sitting corner. Some of these rooms also have a private terrace overlooking the Tuscan hills. They’re characterized by warm colours, welcoming atmospheres and are all located in main buildings of the “Borgo”. These rooms size ranges from 49 to 51 sq. mt. / 527 to 559 sq. ft. EXTRA BED: not allowed - maximum occupancy is 2 persons. BABY Crib free of charge: for babies up to 2 years old.
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Junior suite
*Room image not available
Outfitted with elegant furnishings in shades of the tuscan countryside, th... Read More
Junior suite
*Room image not available
Outfitted with elegant furnishings in shades of the tuscan countryside, the junior suite offers a master bedroom with a light-filled sitting corner and bathroom with walk-in rain shower and separate soaking tub. It is situated within the main quarter of the borgo. Select suites also feature a private furnished terrace with views of the borgo and surrounding countryside.
Outfitted with elegant furnishings in shades of the tuscan countryside, the junior suite offers a master bedroom with a light-filled sitting corner and bathroom with walk-in rain shower and separate soaking tub. It is situated within the main quarter of the borgo. Select suites also feature a private furnished terrace with views of the borgo and surrounding countryside.
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Borgo Suite
*Actual room may differ from image shown
The Borgo Suites are characterized by spacious living room and separate lar... Read More
Borgo Suite
*Actual room may differ from image shown
The Borgo Suites are characterized by spacious living room and separate large master bedroom with bathroom. They distinguish themselves by airy spaces, finely furnished details and typical Tuscan-countryside colors. They are located in the main buildings of the “Borgo”.
Room size: 6 - 9 m2 / 61 - 102 ft2
Room size: 6 - 9 m2 / 61 - 102 ft2
The Borgo Suites are characterized by spacious living room and separate large master bedroom with bathroom. They distinguish themselves by airy spaces, finely furnished details and typical Tuscan-countryside colors. They are located in the main buildings of the “Borgo”.
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Terrace suite
*Room image not available
Located on the ground floor, the one-bedroom terrace suite is comprised of... Read More
Terrace suite
*Room image not available
Located on the ground floor, the one-bedroom terrace suite is comprised of an airy living room, spacious master bedroom, bathroom with walk-in rain shower and separate soaking tub, walk-in closet and guest powder room. Enveloped in warm hues and the soft glow of the tuscan sun, the suite opens to a large furnished terrace or shady pergola.
Located on the ground floor, the one-bedroom terrace suite is comprised of an airy living room, spacious master bedroom, bathroom with walk-in rain shower and separate soaking tub, walk-in closet and guest powder room. Enveloped in warm hues and the soft glow of the tuscan sun, the suite opens to a large furnished terrace or shady pergola.
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Castiglion del bosco suite
*Room image not available
Bespoke florentine furnishings, custom textiles and exquisite appointments... Read More
Castiglion del bosco suite
*Room image not available
Bespoke florentine furnishings, custom textiles and exquisite appointments distinguish the one-bedroom cdb suite. This expansive suite features a living room, generously sized master bedroom, walk-in closet and spacious bathroom with walk-in rain shower and separate soaking tub. Select suites also offer a guest powder room and a private furnished terrace. At a glance size average 1, 329 ft² / 124 m² beds one king bed bathrooms one full bathroom; some with powder room extra bed one bed; one crib view borgo or valley location ground or first floor
Bespoke florentine furnishings, custom textiles and exquisite appointments distinguish the one-bedroom cdb suite. This expansive suite features a living room, generously sized master bedroom, walk-in closet and spacious bathroom with walk-in rain shower and separate soaking tub. Select suites also offer a guest powder room and a private furnished terrace. At a glance size average 1, 329 ft² / 124 m² beds one king bed bathrooms one full bathroom; some with powder room extra bed one bed; one crib view borgo or valley location ground or first floor
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Villa alba
*Room image not available
Situated on a quiet rise near the borgo and winery amongst centuries-old tr... Read More
Villa alba
*Room image not available
Situated on a quiet rise near the borgo and winery amongst centuries-old trees and lush tuscan gardens, villa alba offers magical views over the val d’orcia. This former stone farmhouse has been transformed into a delightful three-bedroom hideaway with comfortable furnishings and beautifully preserved original features. The two-story villa has a separate guest annex, pool and shaded panoramic terrace for outdoor entertaining. At a glance size 2, 819 ft² / 261 m² beds two king beds/ two twin beds bathrooms three full bathrooms/ one powder room occupancy 6 extra bed cribs only view valley location countryside; 1 km (0.6 miles) from the borgo
Situated on a quiet rise near the borgo and winery amongst centuries-old trees and lush tuscan gardens, villa alba offers magical views over the val d’orcia. This former stone farmhouse has been transformed into a delightful three-bedroom hideaway with comfortable furnishings and beautifully preserved original features. The two-story villa has a separate guest annex, pool and shaded panoramic terrace for outdoor entertaining. At a glance size 2, 819 ft² / 261 m² beds two king beds/ two twin beds bathrooms three full bathrooms/ one powder room occupancy 6 extra bed cribs only view valley location countryside; 1 km (0.6 miles) from the borgo
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Villa castello
*Room image not available
Rising dramatically from a sylvan hill overlooking the borgo, villa castel... Read More
Villa castello
*Room image not available
Rising dramatically from a sylvan hill overlooking the borgo, villa castello is built on the ruins of a medieval castle. The timeless three-story, three-bedroom tuscan retreat features cozy interiors replete with luxe textiles and rustic decorative touches. Outside, in the embrace of verdant gardens, shaded living and dining areas and a glistening pool capture panoramic views of the rolling countryside. At a glance size 3, 800 ft² / 353 m² beds two king beds; two twin beds bathrooms three full bathrooms; one powder room occupancy 6 extra bed three beds; cribs view valley location steps from the borgo
Rising dramatically from a sylvan hill overlooking the borgo, villa castello is built on the ruins of a medieval castle. The timeless three-story, three-bedroom tuscan retreat features cozy interiors replete with luxe textiles and rustic decorative touches. Outside, in the embrace of verdant gardens, shaded living and dining areas and a glistening pool capture panoramic views of the rolling countryside. At a glance size 3, 800 ft² / 353 m² beds two king beds; two twin beds bathrooms three full bathrooms; one powder room occupancy 6 extra bed three beds; cribs view valley location steps from the borgo
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Villa casa del fiume
*Room image not available
Tucked away in one of the undulating valleys that shape the estate’s northe... Read More
Villa casa del fiume
*Room image not available
Tucked away in one of the undulating valleys that shape the estate’s northeastern corner, the four-bedroom villa casa del fiume offers glorious views over montalcino. This once-rustic, two-story building has been transformed into an exquisitely private, elegantly appointed tuscan country villa with a separate guest / pool house, swimming pool, tennis court and expansive terraces. At a glance size 5, 518 ft² / 512 m² beds two king beds; four twin beds bathrooms four full bathrooms; one powder room occupancy 8 extra bed four beds; cribs view valley location countryside; 4.7 km (2.9 miles) from the borgo
Tucked away in one of the undulating valleys that shape the estate’s northeastern corner, the four-bedroom villa casa del fiume offers glorious views over montalcino. This once-rustic, two-story building has been transformed into an exquisitely private, elegantly appointed tuscan country villa with a separate guest / pool house, swimming pool, tennis court and expansive terraces. At a glance size 5, 518 ft² / 512 m² beds two king beds; four twin beds bathrooms four full bathrooms; one powder room occupancy 8 extra bed four beds; cribs view valley location countryside; 4.7 km (2.9 miles) from the borgo
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Villa Oliviera
*Actual room may differ from image shown
Originally home to the estate’s olive press, villa oliviera is situated in... Read More
Villa Oliviera
*Actual room may differ from image shown
Originally home to the estate’s olive press, villa oliviera is situated in a secluded spot overlooking the borgo. Here, tuscan tradition meets subtle modern comforts in the three spacious suites enhanced by original features and fireplaces. The breathtaking views from the terraces and the infinity pool provide glimpses of nearby montalcino. The villa can sleep up 6 people.
Originally home to the estate’s olive press, villa oliviera is situated in a secluded spot overlooking the borgo. Here, tuscan tradition meets subtle modern comforts in the three spacious suites enhanced by original features and fireplaces. The breathtaking views from the terraces and the infinity pool provide glimpses of nearby montalcino. The villa can sleep up 6 people.
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Villa chiusa
*Room image not available
Formerly the village police station, the four-bedroom villa chiusa has bee... Read More
Villa chiusa
*Room image not available
Formerly the village police station, the four-bedroom villa chiusa has been wonderfully reimagined as a warm and welcoming vacation home. Offering a finely calibrated rustic-chic sensibility, the living and dining rooms of this two-story villa open to a terrace and infinity pool with spectacular panoramic views of the valley and nearby montalcino. An elegant guest annex and pool house add to the allure of this tuscan escape. At a glance size 3, 897 ft² / 362 m² beds three king beds; two twin beds bathrooms four full bathrooms; two powder rooms occupancy 8 extra bed four beds; cribs view valley and borgo location steps from the borgo
Formerly the village police station, the four-bedroom villa chiusa has been wonderfully reimagined as a warm and welcoming vacation home. Offering a finely calibrated rustic-chic sensibility, the living and dining rooms of this two-story villa open to a terrace and infinity pool with spectacular panoramic views of the valley and nearby montalcino. An elegant guest annex and pool house add to the allure of this tuscan escape. At a glance size 3, 897 ft² / 362 m² beds three king beds; two twin beds bathrooms four full bathrooms; two powder rooms occupancy 8 extra bed four beds; cribs view valley and borgo location steps from the borgo
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Villa sant'anna
*Actual room may differ from image shown
Perched on a ridge overlooking castiglion del bosco golf course and the sou... Read More
Villa sant'anna
*Actual room may differ from image shown
Perched on a ridge overlooking castiglion del bosco golf course and the south-facing sangiovese vineyards, villa sant’anna enjoys a wealth of enchanting views from dawn to dusk. The warmly elegant interiors stand out for their exquisite details, the beautiful natural stone fireplace and understated rooms, with just a few concessions to modern technology permitted in the reading room / home theater room. The extensive private gardens also include a private tennis court. The villa can sleep up to 9 people.
Perched on a ridge overlooking castiglion del bosco golf course and the south-facing sangiovese vineyards, villa sant’anna enjoys a wealth of enchanting views from dawn to dusk. The warmly elegant interiors stand out for their exquisite details, the beautiful natural stone fireplace and understated rooms, with just a few concessions to modern technology permitted in the reading room / home theater room. The extensive private gardens also include a private tennis court. The villa can sleep up to 9 people.
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Villa gauggiole
*Room image not available
Surrounded by golden vineyards and tranquil gardens, the four-bedroom vill... Read More
Villa gauggiole
*Room image not available
Surrounded by golden vineyards and tranquil gardens, the four-bedroom villa gauggiole was once home to a family of farmers. The exceptionally private, two-story domicile has been carefully restored to reveal the authentic tuscan craftsmanship of the original stone walls and timbered ceilings. Modern comforts and luxurious furnishings lend the home an atmosphere of relaxed sophistication. Pastoral views of the vineyards, woods and gentle hills are glimpsed from outdoor living spaces and the pool. At a glance size 6, 238 ft² / 579 m² beds three king beds; two twin beds bathrooms four full bathrooms; two powder rooms occupancy 8 extra bed four beds; cribs view valley location countryside; 3.6 km (2.3 miles) from the borgo
Surrounded by golden vineyards and tranquil gardens, the four-bedroom villa gauggiole was once home to a family of farmers. The exceptionally private, two-story domicile has been carefully restored to reveal the authentic tuscan craftsmanship of the original stone walls and timbered ceilings. Modern comforts and luxurious furnishings lend the home an atmosphere of relaxed sophistication. Pastoral views of the vineyards, woods and gentle hills are glimpsed from outdoor living spaces and the pool. At a glance size 6, 238 ft² / 579 m² beds three king beds; two twin beds bathrooms four full bathrooms; two powder rooms occupancy 8 extra bed four beds; cribs view valley location countryside; 3.6 km (2.3 miles) from the borgo
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Villa stabbi
*Room image not available
From the heights of a picturesque ridge, the five-bedroom villa stabbi enj... Read More
Villa stabbi
*Room image not available
From the heights of a picturesque ridge, the five-bedroom villa stabbi enjoys broad views over the gently rolling sienese countryside. Composed of stone, the two-story home features atmospheric tuscan interiors and a wraparound terrace that looks out to ancient oaks and magnificent sunsets. A separate guest annex, pool and pool house are situated amongst the mature gardens of this exceedingly private retreat. At a glance size 6, 305 ft² / 586 m² beds three king beds; three twin beds bathrooms five full bathrooms; one powder room occupancy 9 extra bed four beds; cribs view valley location countryside; 3.7 km (2.3 miles) from the borgo
From the heights of a picturesque ridge, the five-bedroom villa stabbi enjoys broad views over the gently rolling sienese countryside. Composed of stone, the two-story home features atmospheric tuscan interiors and a wraparound terrace that looks out to ancient oaks and magnificent sunsets. A separate guest annex, pool and pool house are situated amongst the mature gardens of this exceedingly private retreat. At a glance size 6, 305 ft² / 586 m² beds three king beds; three twin beds bathrooms five full bathrooms; one powder room occupancy 9 extra bed four beds; cribs view valley location countryside; 3.7 km (2.3 miles) from the borgo
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Villa biondi
*Room image not available
The most spacious villa to grace the estate, the five-bedroom villa biondi... Read More
Villa biondi
*Room image not available
The most spacious villa to grace the estate, the five-bedroom villa biondi is located on the cypress-lined avenue that runs alongside the golf course. Immersed in the idyllic sienese countryside, this extraordinary tuscan residence radiates warmth and relaxed sophistication. Surrounded by beguiling herb-scented gardens, the two-story retreat offers shaded terraces, a swimming pool and a pool house. At a glance size 7, 815 ft² / 726 m² beds three king beds; four twin beds bathrooms five full bathrooms; two powder rooms occupancy 10 extra bed three beds; cribs view valley location countryside; 2.5 km (1.5 miles) from the borgo
The most spacious villa to grace the estate, the five-bedroom villa biondi is located on the cypress-lined avenue that runs alongside the golf course. Immersed in the idyllic sienese countryside, this extraordinary tuscan residence radiates warmth and relaxed sophistication. Surrounded by beguiling herb-scented gardens, the two-story retreat offers shaded terraces, a swimming pool and a pool house. At a glance size 7, 815 ft² / 726 m² beds three king beds; four twin beds bathrooms five full bathrooms; two powder rooms occupancy 10 extra bed three beds; cribs view valley location countryside; 2.5 km (1.5 miles) from the borgo
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Villa oddi
*Room image not available
Offering blissful seclusion in the heart of the countryside, the six-bedro... Read More
Villa oddi
*Room image not available
Offering blissful seclusion in the heart of the countryside, the six-bedroom villa oddi exudes sophistication and charm. Suffused in natural light, the home’s spacious interiors marry chic tuscan décor with heritage elements such as the farmhouse’s original vaulted brick ceilings. Outfitted with numerous high-tech features, the stone-clad, two-story residence features a screening room, guest / pool house, tennis court, infinity pool and shaded terraces with sweeping views of montalcino. Villa oddi is equally suited to family reunions and business retreats. At a glance size 5, 016 ft² / 466 m² beds four king beds; four twin beds bathrooms six full bathrooms occupancy 12 extra bed five beds; cribs view valley location countryside; 4.7 km (2.9 miles) from the borgo
Offering blissful seclusion in the heart of the countryside, the six-bedroom villa oddi exudes sophistication and charm. Suffused in natural light, the home’s spacious interiors marry chic tuscan décor with heritage elements such as the farmhouse’s original vaulted brick ceilings. Outfitted with numerous high-tech features, the stone-clad, two-story residence features a screening room, guest / pool house, tennis court, infinity pool and shaded terraces with sweeping views of montalcino. Villa oddi is equally suited to family reunions and business retreats. At a glance size 5, 016 ft² / 466 m² beds four king beds; four twin beds bathrooms six full bathrooms occupancy 12 extra bed five beds; cribs view valley location countryside; 4.7 km (2.9 miles) from the borgo
Hours of Operation are in Pacific Standard Time
Hours of Operation are in Pacific Standard Time
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Hotel Policies
Awards & Affiliates
Rosewood Castiglion del Bosco is part of Rosewood Hotels & ResortsCondé Nast Traveler - Hot List Hotel - 2009