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Rosewood Castiglion del Bosco

Tuscany, Italy • Val d'Orcia • OVER THE TOP

avg. $2,339 / night

Includes $123 / night in cash back

Cash back is redeemable via Virtual Visa, Venmo, or bank transfer starting 24-48 hours after check-out

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Free breakfast

Breakfast-included rate options available

Room upgrades

Complimentary room upgrades (subject to property availability)

Extend your stay

Early check-in and late check-out (subject to property availability)

Location

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At a glance

A twelfth-century Tuscan borgo with suites in original farmhouses, restored by Ferragamo and set above Val d'Orcia vineyards.

Best for: Collectors and aesthetes seeking Tuscan authenticity

Highlights:

  • Medieval borgo from the twelfth century, restored by the Ferragamo family
  • 39 suites distributed across original stone farmhouses, not a unified hotel building
  • Infinity pool terraced into hillside overlooking Val d'Orcia olive groves
Aristocratic-pastoral

PB hotel design editorial

One of the oldest continuously farmed estates in the Val d'Orcia, the medieval borgo at the heart of Castiglion del Bosco dates to the twelfth century, its stone towers and honey-coloured farmhouses arranged across a hilltop in the manner of a self-contained village rather than a single grand house. Rosewood Castiglion del Bosco, which opened in 2012 after an extensive restoration led by the Ferragamo family, preserves that settlement logic — 39 suites distributed across the original borgo buildings, so that guests move between cypress allées and kitchen gardens rather than along hotel corridors. The interiors carry a confident aristocratic ease. Rooms in the main villa show coffered ceilings in pale painted timber, herringbone parquet floors, and curtains in pooled silk falling from iron rods — a layering of textures that suggests an inherited house furnished over generations rather than a decorator's brief executed in one pass. Striped fabric headboards in muted gold and taupe anchor the larger suites, with upholstered chaises positioned toward the French doors that open onto stone terraces with views across the Orcia valley. The restaurant terrace, shaded by a retractable burgundy canopy, frames Montalcino on the opposite hillside as a kind of living backdrop to dinner. Below the borgo, a travertine-edged infinity pool cut into the terraced hillside dissolves into the olive groves and rolling wheat fields that have defined this landscape since the Sienese Renaissance.

Travel notes

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About

Situated within the UNESCO-listed Val d'Orcia Natural Park and in the heart of the Brunello di Montalcino wine-making region, Rosewood Castiglion del Bosco is a 5000-acre country estate.Today, Rosewood Castiglion del Bosco is a unique combination: it's one of Tuscany's largest private estates; it's an elegant Tuscan home away from home with 42 elegant and spacious suites and 11 exclusive villas; it's a superb culinary destination, an exclusive private golf club and a leading Brunello di Montalcino winery.

Amenities

Pool

Internet

Free Internet

Free Parking

Restaurant

Wifi

Free Wifi

Room service

Fitness center

Pets Allowed

Rosewood Castiglion del Bosco Reviews

586 reviews

"The property is magnificent. Never been anywhere like it. The food the service the rooms. All perfect. Took a cooking class with ERASMO that was a highlight!!"

A Tripadvisor traveler review

Apr 28, 2026

"The hotel is excellent, the location is a bit remote but it takes a while to understand and really experience the quietness of Tuscany. The breakfast and the food in general is superb. The staff is very friendly and helpful and the reaction time when you want something is so quick which creates a very strong sense of luxury. The only thing is that spa is very small so you have to book in advance. And also you would need a car to go nearby places if you are staying for a long time."

A Tripadvisor traveler review

Mar 25, 2026

"Just magical. The long, winding track leading to Castiglion Del Bosco brings you into it’s dream world, a bubble where every detail is so splendidly perfect it’s hard to imagine anything better. After a long day of travelling with our 2 year old we relaxed immediately when we were warmly welcomed to the hotel and realised we had arrived somewhere extraordinarily special. We were lucky enough to meet Babbo Natale in his beautiful Christmas house on the way to our room which made our little man very happy and set the tone for the rest of our enchanting stay. The setting is spectacular, nestled amongst serene forests filled with wildlife. Spotting Santa’s reindeer one misty morning added to the Christmas magic. This is a very family friendly hotel and so much thought has been put into creating wonderful experiences for families - from the entertainment and activities put on to bring families together, the provisions in the rooms (toys, balloons, sweets, toiletries etc) and the restaurant staff who perfectly anticipated our needs (eg having the highchair ready at our favourite table when we arrived for dinner and immediately preparing his pasta). It's rare to find a place where you can be surrounded by such luxury and feel comfortable for your 2 year old to run around behaving like a 2 year old! He was even welcomed to come along for our wine tasting where he was provided with colouring and a selection of juices to taste. Every member of staff we met was helpful, warm, sincere and treated us like family. Rooms, food and facilities were all outstanding. Noteworthy was the outdoor swimming pool which had been covered by an impressive marquee structure which made the pool completely usable (and very warm) during the winter months. We absolutely loved our stay and I can't wait to return. My only complaint is that we had professional photos taken with Santa but the hotel seems to have lost them. I am quite upset that we never got to see them as my son loved meeting Santa and posed beautifully for the photos."

A Tripadvisor traveler review

Jan 06, 2026

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