Villa il Castagno Wine & Resort

Hotel Description

You know what? I wasn’t expecting much when I first pulled up the gravel drive on SP102 – honestly, the approach feels a bit industrial with all the olive processing facilities nearby. But then Villa il Castagno opens up in front of you and it’s this gorgeous converted farmhouse that somehow manages to feel both authentic and polished. The whole property sits on this gentle hillside about 15 minutes southeast of Siena’s centro storico, and I mean, the views across the Chianti countryside are exactly what you’re picturing when you think “Tuscan wine country.” The staff actually knows their stuff about the wines they’re producing on-site (this isn’t just a hotel with a vineyard slapped on for show), and the tasting room has this relaxed vibe where you can just settle in with a glass of their Sangiovese and watch the sun do its thing over the rolling hills.

The rooms are what you’d hope for in a place like this – think exposed beams and terracotta floors, but with proper air conditioning and WiFi that actually works, which honestly can be hit-or-miss in these converted agriturismi. I stayed in one of the suites facing the vineyards, and there’s something pretty magical about waking up to mist hanging over the vines, especially in late September when harvest season is ramping up. The restaurant leans heavily into that farm-to-table thing, but it doesn’t feel forced – they’re literally growing vegetables in the garden out back, and the chef has this way of doing simple preparations that let the ingredients shine. Fair warning though: dinner service can run a bit slow during peak season (July and August get crazy busy), but that’s kind of the point, right? You’re not here to rush.

What really sets this place apart is how it manages to feel like a proper wine estate without being pretentious about it. The pool area is tucked into the hillside in a way that gives you privacy but doesn’t block those killer views, and there’s enough space that it never feels crowded even when the hotel’s full. Parking is easy – just pull right up to the main building – and they’re super helpful with dinner reservations in Siena if you want to venture into town. The SP102 can get a little busy during the day with trucks heading to the industrial area, but it quiets down completely by evening, and honestly, you’re far enough from the road that it’s never really an issue. If you’re looking for that quintessential Tuscan experience without the tourist circus of some of the more famous wine regions, this spot delivers in a way that feels genuine rather than manufactured.

Rooms

• Estimated price from: $316. Standard Suite with 1 large double bed for Max persons: 2
• Estimated price from: $316. Standard Suite with 1 extra-large double bed and 2 single beds for Max persons: 2
• Estimated price from: $351. Junior Suite with 1 extra-large double bed and 1 single bed for Max persons: 2
• Estimated price from: $351. Junior Suite with 1 large double bed for Max persons: 2
• Estimated price from: $351. Junior Suite with 1 large double bed for Max persons: 2
• Estimated price from: $351. Junior Suite with 1 large double bed for Max persons: 2
• Estimated price from: $409. Senior Suite with 1 extra-large double bed and 2 single beds for Max persons: 2
• Estimated price from: $409. Senior Suite with 2 single beds and 1 large double bed for Max persons: 2
• Estimated price from: $491. Deluxe Suite with Spa Bath with 2 single beds and 1 large double bed for Max persons: 2
• Estimated price from: $491. Deluxe Suite with Spa Bath with 1 single bed and 1 large double bed for Max persons: 2

Reviews

• Exceptional – Anat from Israel – 7 July 2025 (10/10)

  Beautiful place, rooms were spacious, clean and comfortable, we loved the view, staff were very welcoming and helpful. We had lunch and breakfast and we enjoyed the food a lot!

• Relaxing, calm and friendly establishment. – Shelley from United Kingdom – 3 July 2025 (9/10)

  We loved the peace and quiet with the beautiful views of the Tuscan countryside.
  The swimming pool is a lovely relaxing oasis. The staff were very friendly and accommodating.
  
  What could be improved: The lunchtime menu was the same as the dinner menu. We would have ideally liked something a bit lighter at lunch.

• A perfect location with wonderful staff – Robert from United Kingdom – 28 June 2025 (10/10)

  Everything
  
  What could be improved: Nothing

• Beautiful resort in remote area with car access to many beautiful villages. 2-3 nights probably sufficient. – Paula from United Kingdom – 25 June 2025 (9/10)

  Beautiful resort with setting that exceeded expectations and facilities especially the pool area were great also. Helpful staff at both reception and restaurant service.
  
  What could be improved: No real ability to sit outside of room in evenings other than at restaurant/bar with others – an outside area for private time would have been nice after long days travel. Also I really felt a welcome drink or bottle of wine might have been provided as was the case in two of our much less costly locations. Given this was a winery I think a trick has been missed.

• Many thanks to Noemi and her excellent staff for providing us with great services during our stay at the resort. The fac – Thomas from Australia – 22 June 2025 (10/10)

  Management and staff were excellent.
  The property and location were superb
  
  What could be improved: Nothing whatsoever.

• Exceptional – Brian from United States – 13 June 2025 (10/10)

  The property was beautiful, and the staff was outstanding. They went above and beyond. When we asked a question, they offered to take care of it for us. They gave great referrals for restaurants in the area They were amazing. I will definitely return.

• Magical place ! – Kazem from Kuwait – 12 June 2025 (10/10)

  The place was like magic. It was beautiful, calm and the staff were like a family members.
  Room was spacious and the whole facility was 10/10.
  I was there for 4 days and wish I didn’t have to leave

• Best staff, beautiful accommodations and perfect views. The incredible food and wine! – Surrett from United States – 25 May 2025 (10/10)

  Incredible views. Very relaxing and perfectly appointed.

• Our stay was wonderful — warm, smiley staff, amazing Tuscan views, delicious food, great wine and olive oil, all made ev – Alp from United Kingdom – 3 May 2025 (10/10)

  We had a fantastic stay at Villa il Castagno. Our corner room on the top floor offered breathtaking views of the Tuscan vineyards and iconic cypress trees — a truly unforgettable sight. The building itself is charming, with classic stone walls and tasteful interior decoration that adds to the authentic feel.
  
  The room was spacious, clean, and well-appointed, featuring a modern bathroom, a smart TV, and a fast internet connection — perfect for relaxing after a day of exploring. We couldn’t have asked for a better base to experience the region. Highly recommended!

• Very good – Ofer from Israel – 20 April 2025 (8/10)

  Amazing place, beautiful views.
  
  What could be improved: Breakfast was very poor, and so was dinner in the restaurant. It's a pity, because if dining was at an equal standard as the accommodations, my rating would have been much higher.

SURROUNDINGS

Facilities