Rosewood Castiglion Del Bosco

Montalcino, Italy

9.8 Superior Luxury

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We recommend booking a stay with free cancellation in case your plans change.

O3K
Villa Oliviera, at Rosewood Castiglion Del Bosco

Villa Oliviera

  • Originally home to the estates olive press, Villa Oliviera occupies a secluded spot overlooking the Borgo
  • Here, Tuscan tradition is updated with subtle modern comforts in three spacious suites enhanced by original features and fireplaces
  • The marvelous views from the terraces and infinity pool provide glimpses of nearby Montalcino
  • 4,500 sq feet (418 sq meters)

USD $ 3,488 /nt

Limited availability.

ADVANCE PURCHASE RATE

Once booked, this rate cannot be canceled without penalty.

USD $3,488 /nt
$10,464 for 3 nights
including taxes & fees
Price breakdown

V3K
Villa Castello, at Rosewood Castiglion Del Bosco

Villa Castello

  • Perched atop a hill overlooking the Borgo on the ruins of a medieval castle, the Villa Castello offers one of the coziest interiors on the estate
  • The three-story retreat also boasts a beautiful swimming pool and a lovely garden with captivating views over the timeless Tuscan landscape
  • 3,800 sq feet (353 sq meters)
  • First floor bedroom 1: King Bed

USD $ 3,488 /nt

Limited availability.

ADVANCE PURCHASE RATE

Once booked, this rate cannot be canceled without penalty.

USD $3,488 /nt
$10,464 for 3 nights
including taxes & fees
Price breakdown

V4K
Villa (Casa del Fiume), at Rosewood Castiglion Del Bosco

Villa (Casa del Fiume)

  • 2 King Beds
  • 5511 sq feet (512 sq meters)
  • Individually decorated room, furnished balcony/patio with valley and hill views
  • 4 bedrooms, living room, and dining area

USD $ 4,767 /nt

Limited availability.

ADVANCE PURCHASE RATE

Once booked, this rate cannot be canceled without penalty.

USD $4,767 /nt
$14,301 for 3 nights
including taxes & fees
Price breakdown

O4K
Villa Chiusa, at Rosewood Castiglion Del Bosco

Villa Chiusa

  • 362 sq meters. / 3,897 sq feet
  • Borgo and valley view
  • Three king beds and two twin beds
  • Formerly the village police station, the four-bedroom Villa Chiusa has been carefully restored and converted into a warm, enticing retreat, complete with an elegant guest annex, pool house and terrace

USD $ 4,767 /nt

Limited availability.

ADVANCE PURCHASE RATE

Once booked, this rate cannot be canceled without penalty.

USD $4,767 /nt
$14,301 for 3 nights
including taxes & fees
Price breakdown

V4D
Villa Gauggiole, at Rosewood Castiglion Del Bosco

Villa Gauggiole

  • Surrounded by vineyards, Villa Gauggiole was once home to a large farming family
  • The villa has been beautifully restored to reveal the origins of the building in the stone walls and original ceiling beams
  • At the same time, modern comforts and luxurious furnishings were added, lending the home an atmosphere of relaxed sophistication
  • 6,203 sq feet (580 sq meters)

USD $ 4,767 /nt

Limited availability.

ADVANCE PURCHASE RATE

Once booked, this rate cannot be canceled without penalty.

USD $4,767 /nt
$14,301 for 3 nights
including taxes & fees
Price breakdown

VLK
Villa Agresto, at Rosewood Castiglion Del Bosco

Villa Agresto

  • Intimately secluded in the estate wood and proudly dominating a breath-taking view over Montalcino, Siena and Pienza, Villa Agresto sits on a panoramic clearing and is surrounded by olive trees and its own private vineyard
  • Featuring 5 double bedrooms, a fully equipped kitchen, a bright white cozy and embracing living room with original fireplace, and a shaded internal patio
  • This Villa has a one-of-a-kind infinity pool with a picture-perfect view
  • 4,973 sq feet (462 sq meters)

USD $ 6,046 /nt

Limited availability.

ADVANCE PURCHASE RATE

Once booked, this rate cannot be canceled without penalty.

USD $6,046 /nt
$18,137 for 3 nights
including taxes & fees
Price breakdown

Please note, room photos and descriptions are representative of the room category. Actual rooms may vary from what is shown.

About the Hotel

Located within the UNESCO-listed Val d’Orcia in the Brunello di Montalcino wine-making region, Rosewood Castiglion del Bosco is a 5,000 acre country estate founded by Massimo and Chiara Ferragamo. The Italian resort is a celebration of the natural beauty and rich gastronomic heritage of Tuscany. The 800-year-old estate comprises the ancient castle ruins, a medieval church and the Borgo, a historic village that now forms the heart of the resort.

Location

Rosewood Castiglion Del Bosco
Località Castiglion del Bosco
Montalcino, Italy 53024

Nearest Airport: FLR

Features and Amenities

  • Dining
  • Bar
  • Restaurants
  • On-Site Amenities
  • Pool
  • Spa Services
  • Fitness Center
  • Wellness Center
  • In-Room Amenities
  • Private Pools
  • Activities
  • Excursions
  • Tennis
  • Golf
  • Nearby
  • Historic Sites
  • Interests
  • Golf
  • Hotels
  • Spa
  • UNESCO Site Nearby

Reviews for Rosewood Castiglion Del Bosco

Want to live there!

TripAdvisor Traveler Review Rating Reviewed 3 days ago

You can say you’re in paradise. Can we give a 6 star? The property is amazing, staff is welcoming and always there to make it happen and not say no to your needs. They really go beyond expectations. We’re celebrating 25Th anniversary and after we had dinner at their 2 star Michelin our bathtub was filled, warm and ready to go. Decorated with candles, flowers etc Everything is so beautiful that you want to be there forever as it’s such a welcoming place. 2 modern pools, 2 restaurants, a winery and we also played tennis. Want to go back soon. We love you Rosewood CDBosco team.

Samuel B


disappointing experience at Castiglion del Bosco

TripAdvisor Traveler Review Rating Reviewed 2 weeks ago

I feel compelled to share my deeply disappointing experience at Castiglion del Bosco to prevent other guests from facing a similar ordeal. My stay was severely marred by multiple, significant service failures, including a complete breakdown with the pre-arranged photographer, issues with a drone service, and a problematic payment process. These were not minor inconveniences; they fundamentally ruined the holistic vacation experience we had paid a premium for. Worse than the initial failures, however, has been the hotel's response to our formal complaint. Despite a cordial call, their final resolution was a conditional, partial gesture that ignored the core issues. They have now categorically refused a refund and, when confronted with a separate health-related concern from their Spa, have shifted all responsibility by demanding that we, the client, file a claim with their insurance provider. This is not how a luxury brand that claims to value its guests should operate. True luxury is reflected not just in the amenities but in accountability and customer care when things go wrong. Castiglion del Bosco has demonstrated a complete lack of both. Instead of taking ownership, they have chosen a path that forces the guest into a protracted and burdensome legal dispute. I am now left with no choice but to pursue my consumer rights through official channels. Proceed with extreme caution. The beauty of the property is undeniable, but the risk is substantial. When problems arise, you will be on your own. Recommendation: Not Recommended.

Alexandru Z


Beyond perfect.

TripAdvisor Traveler Review Rating Reviewed 3 weeks ago

Some places are so extraordinary they feel almost unreal. Rosewood Castiglion del Bosco is one of them. Perched high on a Tuscan hill, it is an old village brought back to life, every stone and path restored with reverence and style. The setting is nothing short of breathtaking. Rolling vineyards, cypress trees and golden light stretch to the horizon. The views alone are worth the trip, but the hotel itself is even more impressive. The rooms are vast and elegant, the kind you could happily live in forever. Every detail feels handpicked, blending old-world character with modern comfort. The staff are exceptional, discreet yet warm, and they make the whole experience feel effortless. The food is as memorable as the views. From intimate dinners to the brilliant Street Festival buffet-style evening, every meal is an event and every bite a reminder of how good life can be. Service throughout is flawless, attentive without ever feeling fussy. Verdict: total perfection. Rosewood Castiglion del Bosco is one of the best places I have ever stayed. It is not just a hotel, it is an experience, and one I would return to in a heartbeat.

DJ_RevPlaytime - Monaco


The best hotel stay in all of Europe!

TripAdvisor Traveler Review Rating Reviewed 2 months ago

A World-Class Masterpiece: Rosewood Castiglion del Bosco, Tuscany From the moment my husband and I arrived at the Rosewood in Tuscany, it was clear we were experiencing something truly extraordinary — not just a resort, but one of the finest hotels in the world. Every element is perfection: the warm, professional, and impeccably attentive staff make you feel like the most important guest on property. Our ultra-luxurious villa stay was beyond anything we’ve ever experienced — spacious, exquisitely designed, and effortlessly elegant, topping even the most exclusive five-star resorts globally. The spa deserves special praise — I had the best facial of my life, a one-hour treatment using Officina Profumo-Farmaceutica di Santa Maria Novella products, complete with a facial massage that left my skin glowing and my entire body rejuvenated. Absolute heaven. The concierge team also made the impossible possible by arranging for us at the last minute to attend the Palio di Siena on our second night — a once-in-a-lifetime experience we will never forget. Thanks to them, we saw one of Italy’s most historic and thrilling events up close. The food is exceptional, the wines from the estate vineyard divine, and each meal felt like a celebration of Tuscan culinary artistry. Whether relaxing poolside, exploring the grounds, or sipping a Brunello with a sunset view, every single detail is flawless. A stay here isn’t just a vacation — it’s a once-in-a-lifetime experience that sets an entirely new benchmark for luxury hospitality worldwide.

K M - Tiburon, California


Nightmare staff / overpriced

TripAdvisor Traveler Review Rating Reviewed 3 months ago

Went to check out this venue for my wedding. Granted I was there because my fiancé and I were looking at a full buyout of the property, it is over 1mil for a full buyout for 3 days. However the experience was terrible, first off they made us rent a villa for 17k for two nights for the two of us, we were supposed to be able to see the grounds and different villas, but they wouldn’t let us see inside of them due to “the fact they were being cleaned” I expressed I didn’t care and we would like to see this as it’s important and they wouldn’t let us. The Michelin restaurant on site was not that great, the other restaurant was better. We did not get to experience one aspect of the hotel because we were with the staff viewing the property, and then when we asked for a late checkout (their checkout is at 10am lol) they would not allow it, so this is why we decided not to go with this venue or ever come back here for vacation. Also when they tell you the property is 5000 acres, what they mean to say is their vineyard is 4995 acres and they have 5 acres of actual usable property by the resort.

Woody M


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