Rosewood Castiglion del Bosco

Hotel Description

Look, I’ve stayed at plenty of fancy places in Tuscany, but Rosewood Castiglion del Bosco is honestly in a league of its own. The moment you wind up that cypress-lined drive from Montalcino – and I mean really wind, it’s about 20 minutes of gorgeous hills and vineyards – you realize this isn’t just another luxury hotel. It’s actually a restored medieval village, complete with stone houses scattered across 5,000 acres of the most beautiful countryside you’ve ever seen. The whole place used to be owned by Ferragamo (yes, the shoe guy), and you can tell they didn’t mess around when they restored it.

What really gets me is how they’ve managed to make something this elegant feel surprisingly lived-in. The suites are housed in these ancient stone buildings with thick walls that keep everything perfectly cool even in August heat, and each one feels like your own private villa. I stayed in one of the Estate Suites last spring – honestly, the terrace overlooking the Val d’Orcia made me want to cancel the rest of my trip and just sit there with a glass of their Brunello. Speaking of wine, this place produces some seriously good stuff; their vineyard is right there, and you can actually walk through it without feeling like you’re intruding on some tourist trap. The spa is built into what used to be the village cellars, so you’re literally getting a massage in 800-year-old stone chambers – sounds weird, but it’s incredibly atmospheric.

Here’s the thing though – and this is important – you really need a car here. The nearest town is Montalcino, which is gorgeous but about a 25-minute drive down winding roads. Some people might find that isolating, but honestly, that’s exactly the point. You’re not dealing with crowds or tour buses; you’re in this perfect bubble where the biggest decision is whether to have dinner at the main restaurant or request a private chef for your suite. The staff genuinely knows the area too – they’ll send you to this tiny enoteca in Montalcino that tourists never find, or arrange a truffle hunt that’s not some cheesy show but the real deal with actual locals and their dogs. Check-in was seamless (they handle your luggage while you’re having welcome drinks), and I never heard a single noise from other guests despite the place being full. The pool area gets busy around 2 PM, but honestly, with grounds this massive, you can always find your own quiet spot. It’s expensive, sure, but when you’re watching the sunset over the same hills that inspired Renaissance painters while sipping wine made literally on the property, you sort of forget about the cost.

Rooms

• Estimated price from: $1,575. Suite with 1 extra-large double bed for Max persons: 2
• Estimated price from: $2,588. Deluxe Suite with 1 large double bed for Max persons: 2
• Estimated price from: $2,588. Suite with Terrace with 1 large double bed for Max persons: 2
• Estimated price from: $2,764. Superior Suite with 1 large double bed for Max persons: 2
• Estimated price from: $10,409. Villa with 2 × 1 extra-large double bed and 2 × 2 single beds for Max persons: 8
• Estimated price from: $10,876. Villa with 3 × 1 extra-large double bed and 2 single beds for Max persons: 8
• Estimated price from: $11,168. Villa with 3 × 1 extra-large double bed and 2 single beds for Max persons: 8
• Estimated price from: $13,596. Villa with 3 × 1 extra-large double bed and 2 × 2 single beds for Max persons: 10
• Estimated price from: $13,735. Villa with 3 × 1 extra-large double bed, 2 single beds and 1 single bed for Max persons: 11

Reviews

• Restful, well appointed, high-end resort. – Scott from United States – 31 May 2025 (8/10)

  Location was beautiful, pool(s) were warm, exercise room was fantastic. So many ammendies, from wooden combs to cool face clothes. Spa was small, but nice.
  
  What could be improved: I know it costs a lot of money; I get that. But I think that $50 euros for a buffet breakfast was just taking advantage of their guests!
  Location was beautiful, but isolated, so difficult to get around except for their overpriced transportation options. Therefore, no point in going to the closest town 20 minutes away for your breakfast croissant, it will cost you 115 Euros!

• Exceptional – Guanhua from United Kingdom – 7 December 2024 (10/10)

  This is for sure the best of best! The entire resort is very well maintained and so welcoming. We were well taken care of by the team and our dog spent a great for her birthday.
  
  What could be improved: Well there is. As a couple with the same sex you would expect the hotel to well acknowledge this before they have the room ready for us. However this is not the case when you see two laundry bags as “one for him and the other for her” as usual, and the flip-flops in the bathroom as well.

• The best – Al from United Arab Emirates – 16 September 2024 (10/10)

  Everything was amazing
  
  What could be improved: Food options

• Luxury and wine – Ioannis from United Kingdom – 4 May 2024 (10/10)

  Impeccable atmosphere. Top service. Ideal hideaway for the wine tasting lovers
  
  What could be improved: The Michelin start misses out on vibe and service. Should have been in the winery and focus on local ingredients, not so much on fish

• Great! – Amine from United Kingdom – 16 April 2024 (8/10)

  Amazing hotel, with great facilities and amazing staff
  
  What could be improved: Campo del Drago restaurant (1 Michelin star) was disappointing

• Absolutely stunning hotel, there is some room for improvement for this price point. – Ira from United Kingdom – 24 August 2023 (8/10)

  It is absolutely gorgeous – like a fairytale. The rooms are insane – so so so so big as one may expect given the price. They had lots of food options and organized special dinners which were very nice touch. We enjoyed the Tuscan family style Sunday dinner – excellent meat!!!!
  
  What could be improved: 80% of the staff was outstanding but I have given lower rating on staff because for this price point you expect 100% of the staff to be outstanding. They were all very nice but some were not fully trained yet – we got lukewarm Rose wine vs cold. We had booked a room with a balcony and on arrive they upgraded the room but it didn’t have a balcony which was key for us. In the end they definitely more than fixed the situation by upgrading us to a room with terrace but only after I was asked to show that my reservation included a balcony which was a bit odd.
  The vibe was a bit more rosewood and a bit less Tuscany – which is not necessarily a negative – depends on your taste.

• Amazing – Gabriel from Australia – 5 August 2023 (10/10)

  Everything

• Exceptional – Yanyan from China – 2 May 2023 (10/10)

  Everything is fantastic and especially the staff is so helpful.
  
  What could be improved: no

• A satisfactory Tuscan holiday – Yui from Hong Kong – 25 October 2022 (9/10)

  Very Tuscan experience with several experiences to offer! In house del Bosco Tuscan red wine is worth a taste!
  
  What could be improved: power sockets are not easily accessible in the bedroom.

• Our stay felt like a dream. From the moment we arrived until we felt, the staff was so attentive to every detail. We fou – Elena from United States – 19 September 2022 (10/10)

  The hotel exclusive location and private setting in the middle of Tuscan Hills built from a medieval castle. Magical is an understatement.

SURROUNDINGS

Facilities