Val d'Orcia, ItalyCastiglion del Bosco
Castiglion del Bosco, A Rosewood Hotel
Restored medieval borgo
Castiglion del Bosco Val d'Orcia, Italy
Renovated
2021
Price
$$$$
Rated for
Luxe Heritage ResortOutside the door
The house
RosewoodRestored medieval borgo
Sandstone paths wind through a restored medieval village, where ancient castle ruins overlook rolling vineyards and oak forests across the Tuscan valley.
“The property is spread over 5,000 acres but manages to feel intimate, with 42 stylishly decorated suites and 11 villas.”
What it’s good at
Exceptional
Dedicated estate concierges and chauffeured Land Rover Defender transfers across the property.
Remarkable
A twelfth-century church with Pietro Lorenzetti frescoes, set among medieval fortress ruins.
Remarkable
A five-thousand-acre estate with private championship golf, winery tastings, and truffle hunts.
What they say
Three Michelin Keys
Michelin
Forbes Five-Star
Forbes Travel Guide
2026
UK Readers' Choice Awards – Europe
Condé Nast Traveler
2025
Also in The 50 Discovery and Wallpaper*.
the intimate hotel portion of Rosewood Castiglion del Bosco is just the tip of the bucolic iceberg — in total, more than 5,000 acres of intact, 900-year-old agricultural estate property provide a spectacular backdrop.
“Managed by Rosewood since 2015, the property today comprises 42 suites and 11 freestanding villas, which were restored from abandoned 17th- and 18th-century farmhouses.”
Tucked away
A place apart: the property is the destination.
Unpaved tracks trace the protected Val d'Orcia landscape, winding past cypress groves and Brunello vineyards toward the hilltop ramparts of Montalcino.
The rooms
Borgo suites feature Florentine textiles and exposed timber beams, while restored farmhouse villas add private heated pools and stone fireplaces.
The infinity pool
Bring a swimsuit.
The stone infinity pool is heated to 28 degrees Celsius and looks across the rolling Val d'Orcia hills.
The spa and gym
A glass-walled fitness studio looks across the hills. In the vaulted brick cellars, the spa houses a Finnish sauna.
Dogs stay too.
Restaurant
Ristorante Campo del Drago
The two-Michelin-starred restaurant serves contemporary Tuscan tasting menus on a terrace overlooking the wooded valley.
The Montalcino hotel’s main infinity pool looks like part of the landscape, its sandstone-colored deck blending in seamlessly with the surrounding vegetation.
At the table
Osteria La Canonica serves stone-oven pizzas along the village street, and the lobby bar pours estate Brunello.
How it began
Massimo and Chiara Ferragamo revitalized the nine-hundred-year-old agricultural village, restoring its medieval church, ancient fortress, and centuries-old farmhouses.
“Preserving the strong foundations of the place and swerving the ostentatious for the refined, the hotel sits across the original hilltop borgo and 11 farmhouses.”
Good to know
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Castiglion del Bosco, A Rosewood Hotel
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Val d'Orcia
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Our shorthand
How we rate hotels.
The medals
Gold
Extremely rare. Sets the global standard.
Silver
Brilliant execution. And we’re picky.
Bronze
They did this well. You’ll notice.
Listed
A defining trait. Makes the hotel what it is.
The eight vibes
Design
Built around a vision. Even the door handles have a designer.
Luxe
Cared for at every turn. The bath is drawn before you ask.
Local
It could only be here. You wake up knowing where you are.
Social
Where the city goes out. The bar is full and the night is young.
Heritage
A building with a story. Once a palace, a monastery, a station.
Wellness
You leave feeling new. Rest, sweat, soak and sleep like a stone.
Classic
The city grew up with it. Same rituals, same regulars, same bar.
Resort
A world of its own. Something to do from breakfast to nightcap.
The scene
Lively
Where things happen: restaurants, shops, people.
Central
Well-located: walkable to some things, a short ride to more.
Quiet
Away from the crowds. Getting around takes intention.
Secluded
A place apart: the property is the destination.