Rosewood Castiglion del Bosco
Rosewood's 800-year-old estate above Montalcino in the Val d'Orcia – a Brunello winery, a private golf course, and five-star standing in a UNESCO landscape.
Rosewood · Chianti, Siena & Val d'Orcia · Florence & Tuscany
A sense of the place
Why it's in the collection
Because an estate eight centuries old, with its own Brunello winery and a private golf course inside the Val d'Orcia's UNESCO landscape, is Tuscany at the scale of a country – and Rosewood runs it with five-star standing.
- An 800-year-old estate above Montalcino, in the Val d'Orcia – a UNESCO World Heritage landscape.
- A Brunello winery on the estate – Montalcino's wine, made on the property.
- A private golf course within the estate.
- Run by Rosewood; Three MICHELIN Keys 2025, and five-star standing.
Suites and rates
Every rate is confirmed with you by the concierge before anything is booked — cancellation terms in plain language, no surprises.
The neighborhood
Chianti, Siena & Val d'Orcia
The countryside south and west of Florence – Chianti's vineyards on the road to Siena, the hill towns from San Gimignano to Montalcino, and the bare, folded valley of the Val d'Orcia beyond – where the other three hotels are estates: a winery, a borgo, and a villa with its farm.
- Montalcino, the Brunello town, below the estate.
- Pienza and the Val d'Orcia road, to the east.
- Siena, to the north.
Reviews
From our editors
Verified guest reviews are coming — we only publish ratings from licensed sources and verified stays.
“Rosewood's 800-year-old estate above Montalcino in the Val d'Orcia – a Brunello winery, a private golf course, and five-star standing in a UNESCO landscape.”
Plan your stay
Tell us your dates and our concierge confirms rates and availability — no payment, no commitment.
Nearby in the collection
Castelfalfi
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From $600 per night
Borgo Santo Pietro
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A 13th-century villa estate near Chiusdino in the Sienese hills – an organic farm, a spa and the Saporium restaurant, independently run to five-star standing.
From $1,200 per night
Four Seasons Hotel Firenze
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Palazzo della Gherardesca and its walled garden, the largest private garden in Florence – a palazzo run by Four Seasons in the centro storico, with five-star standing.
From $1,500 per night