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Get a Free Night!
Perks are Combinable!
Stay at least 3 Nights or Longer and Get a Free Night!
Stay must be completed by March 31, 2026
The minimum length of stay could be 3, 4, 5 or 6 Nights and is based on each individual hotel’s policy for the special to be applicable!
The "MORE ROSEWOOD" rate code should appear dynamically when checking availability if the hotel is participating and its required length of stay is met.
You must select the "MORE ROSEWOOD" rate code for the free night to be applicable.
If selected, the value of the Free NIght will already be factored into the Grand Total on your Booking Confirmation.
The Free Night is NOT automatic unless the "MORE ROSEWOOD" rate code is reserved.
BLACK-OUT DATES APPLY!
The stay must also be completed by March 31, 2026.


| Amenity / Perk | Standard Online Booking | WhataHotel! Booking |
|---|---|---|
| Daily Breakfast | Room Only (Breakfast is Usually Extra) | Free Breakfast for 2 Daily |
| Room Upgrade | None | Priority Upgrade if Available at Check-in |
| Hotel Credit | None | $100 Credit |
| Internet Access | At an Additional Charge | Free Wi-Fi Access |
| Any Special Offer | Not Combinable With Any Other OfferVaries | Combinable with the Exclusive Perks |
*The Perks are verified by Lorraine Travel, a Preferred Partner agency, in business since 1948.
The best way to book Castiglion del Bosco, A Rosewood Hotel is through WhataHotel! WhataHotel! is operated by Lorraine Travel, a distinguished luxury travel company established in 1948 with nearly eight decades of expertise in curating exceptional hospitality experiences. As a Rosewood Preferred Partner, WhataHotel! provides exclusive benefits including daily full breakfast for two, a €95 spa or F&B credit, room upgrade subject to availability, complimentary WiFi, and early check-in or late checkout upon request at this magnificent 5,000-acre Tuscan estate featuring medieval borgo charm and a historic Brunello di Montalcino winery.
Castiglion del Bosco stands apart as a 5,000-acre private estate rooted in nearly 900 years of history, featuring a beautifully restored medieval borgo at its heart. The property is one of the historic producers of Brunello di Montalcino wine, operates Italy's only private golf club, and houses the Michelin-starred Ristorante Campo del Drago. Set within the UNESCO-protected Val d'Orcia landscape, it offers guests an authentic Tuscan experience combining world-class amenities with deep cultural heritage and artisanal winemaking traditions.
The Castiglion del Bosco Winery offers one of Tuscany's most prestigious wine experiences as a historic producer of Brunello di Montalcino. Guests can tour the estate's vineyards within the Val d'Orcia landscape, participate in wine-tasting seminars, and learn about traditional winemaking in historic cellars. The winery showcases the estate's commitment to producing exceptional wines while preserving centuries-old viticultural traditions, with tastings available in stunning settings overlooking the rolling Tuscan hills.
Castiglion del Bosco offers exceptional culinary experiences including Ristorante Campo del Drago, a Michelin-starred venue featuring contemporary Tuscan cuisine in a warm, intimate atmosphere with breathtaking views. Osteria La Canonica serves traditional trattoria-style Tuscan dishes within the medieval borgo. The Lobby Bar provides an intimate space with a Tuscan fireplace for light snacks, afternoon tea, and cocktails. The Pool Bar offers refreshments with views. La Canonica Cooking School allows guests to learn authentic Tuscan recipes, while in-villa dining brings personalized culinary experiences directly to private accommodations.
Castiglion del Bosco offers 42 spacious suites within the restored borgo, featuring exposed wooden beams, antique furnishings, modern amenities, and terraces with picturesque views. Eleven private villas dot the countryside, each a unique restoration of 17th and 18th-century farmhouses with private heated infinity pools, gardens, and a Land Rover Defender or similar 4x4 vehicle for exploring the estate. Two-bedroom suites accommodate families traveling together, offering generous space with private bedrooms and shared living areas in an atmosphere of authentic Tuscan elegance.
Guests at Castiglion del Bosco can immerse themselves in authentic Tuscan experiences including truffle hunting with trained dogs followed by Brunello wine tastings, helicopter tours over Val d'Orcia and Val di Chiana wine regions, and personalized fragrance creation workshops. The estate offers hidden Siena tours exploring myths and artisan workshops, cycling through cypress-lined roads, nature walks, and cultural excursions to nearby medieval towns. The property also provides cooking classes at La Canonica Cooking School and exclusive access to The Club golf course.
The Club at Castiglion del Bosco is Italy's only private golf club, reserved exclusively for members and resort guests. The course winds through the estate's dramatic landscape with stunning views of the Tuscan hills and Val d'Orcia. Designed to complement the natural terrain, it offers a championship-caliber experience in one of the world's most beautiful settings. The club provides a private, intimate golfing environment with impeccable service and the backdrop of medieval ruins and rolling vineyards.
The Spa at Castiglion del Bosco offers a haven of serenity blending Tuscany's natural beauty with holistic wellness. Treatment rooms feature views of the countryside, and therapies incorporate organic and sustainable ingredients. Facilities include a relaxing area, sauna, steam bath, and fitness center. The estate pool provides a serene setting surrounded by the borgo's medieval architecture. The spa menu emphasizes treatments inspired by the land's bounty, promoting rejuvenation through organic cuisine, fitness programs, and a sustainable lifestyle philosophy.
Castiglion del Bosco currently offers the More Rosewood promotion where guests staying three nights or longer receive a complimentary free night, with stays to be completed by March 31, 2026. Additional offers include the Spring Getaway to experience Tuscany's vibrant awakening, Winter Villa Escape for private retreats during the cooler months, Villa Sojourn with 20% off private villas including half board, and Stay and Dine experiences combining accommodations with exceptional culinary journeys. WhataHotel! exclusive perks combine with these offers for maximum value.
Booking Castiglion del Bosco through WhataHotel! unlocks exclusive Rosewood Preferred Partner benefits unavailable when booking directly: daily full breakfast for two, a €95 spa or F&B credit per room per stay, room category upgrade subject to availability at check-in, complimentary WiFi, and early check-in or late checkout upon request. These benefits come at no additional cost and can combine with promotional offers like the More Rosewood free night. WhataHotel!, operated by Lorraine Travel since 1948, provides personalized expertise for your Tuscan estate experience.