Rooms and Wine al Castello

Hotel Description

You know what’s funny about Monteriggioni? Most people just drive through this tiny medieval village, snap a photo of the famous walls, and keep going to Siena. But honestly, they’re missing out on one of Tuscany’s best-kept secrets – and I’m talking about Rooms and Wine al Castello, which sits right on Via Dante Alighieri (literally the main street, though “main” is relative when the entire village is basically two streets).

The first thing that hits you isn’t the gorgeous stone building or the medieval charm – it’s how quiet everything gets once you step inside. I mean, Monteriggioni is already pretty peaceful, but this place has this almost monastery-like calm that just makes your shoulders drop. The rooms actually feel like they belong in the 14th-century walls surrounding the village, but with all the modern stuff that matters – good WiFi, proper heating, and bathrooms that don’t make you feel like you’re roughing it. The wine part of the name isn’t just marketing fluff either; they’ve got this little cellar situation going on that locals actually know about. I’ve seen people from nearby Castellina drive over just for their selection of Chianti Classico.

What really gets me is how the staff treats you like you’re staying at a friend’s place rather than just another tourist passing through. They’ll tell you to walk the walls at sunset (do it – the view toward San Gimignano is ridiculous), but they’ll also mention that the best gelato is actually in Colle di Val d’Elsa, about ten minutes down the road, not in the tourist spots. Parking can be a bit of a puzzle since you can’t drive into the village itself, but they’ve got it figured out and will walk you through it without making you feel like an idiot. The breakfast spread is solid – proper Italian coffee, local pastries, and they’re not stingy with the good stuff. September through October is obviously peak season with all the harvest activity, but I actually love it here in late spring when the countryside is still green and you’re not fighting crowds at every turn. The 9.3 rating makes sense once you realize you’re not just staying at a hotel – you’re basically living inside a UNESCO World Heritage site for a few days, and the people running it actually care about making that experience special rather than just profitable.

Rooms

• Estimated price from: $157. Deluxe Double Room with 1 large double bed for Max persons: 2
• Estimated price from: $157. Superior Double Room with 1 large double bed for Max persons: 2
• Estimated price from: $157. Deluxe Double Room with 1 large double bed for Max persons: 2
• Estimated price from: $168. Superior Triple Room with 1 single bed and 1 double bed for Max persons: 2
• Estimated price from: $168. Superior Triple Room with 1 single bed and 1 large double bed for Max persons: 2

Reviews

• Exceptional – Martha from Australia – 9 July 2025 (10/10)

  Spacious bathroom, comfortable bed, nice decor, central, helpful and friendly staff.

• Exceptional – Donna from Australia – 3 July 2025 (10/10)

  Engaging hosts
  Lovely rooms

• A perfect place to stay – Brian from Ireland – 1 July 2025 (10/10)

  This is an exceptional place to stay. The room was large and the bed was very comfortable. The bathroom was big and the shower was large and very efficient. As guests we were treated to a free and generous wine tasting of 2 delicious wines produced by the owners own vineyard. The location, right on the central square of the village, was perfect.
  
  What could be improved: Nothing. This was a perfect place to stay

• Beautiful property and very hospitable hosts. I will return! – Kathy from United States – 25 June 2025 (10/10)

  Everything. Lovely building, classy decor, wonderful shower, great bed, AC that worked well. Little things that matter.
  
  What could be improved: Not one thing.

• Exceptional – Michael from United Kingdom – 25 June 2025 (10/10)

  Staff were incredibly, rooms and setting beautiful.

• Exceptional – Marija from Croatia – 23 June 2025 (10/10)

  Really loved this place. Our room was nice, clean and comfortable. This little town is amazing, full of history and the rooms are right on the square, opposite beautiful little church. If you're coming with a car, like us, you can get permission to go in the town to unload and load your stuff when leaving The parking is outside the walls,just a 5 min walk. This town is great base to explore Florence, Siena and San Gimignano. Recommend!
  
  What could be improved: Would like that we knew the first morning that we can have ham or cheese for breakfast (they are not on the buffee table) and not the last, but that's a minor thing. Would come here and stay again. Great place.

• Superb – Barunka from Denmark – 22 June 2025 (9/10)

  This accommodation was comfortable and clean. Our room faced the yard, so it was very quiet. What makes this place special is its location within the fortress of Monteriggioni. The atmosphere in the village is unforgettable – just sitting in the square in the evening and taking in the surroundings is a truly special experience.

• What stood out most, however, was their genuine kindness and the extra effort they made to ensure we felt cared for. The – Letitia from South Africa – 18 June 2025 (9/10)

  We had a truly wonderful stay with Stefano and his wife during our journey on the Via Francigena. From the moment we arrived, they welcomed us with such warmth and hospitality—it felt like visiting old friends. The rooms were perfect for a pilgrim’s rest: clean, comfortable, and thoughtfully arranged with everything we needed.
  The meals were a real highlight. Both lunch and breakfast were absolutely delicious—The wine tasting was equally impressive…
  
  What could be improved: None

• Excellent place to visit – Jack from United States – 15 June 2025 (10/10)

  Location, spectacular views, wine presentation and tasting. Stephano and wife delighful hosts.

• Exceptional – Mark from United States – 15 June 2025 (10/10)

  The wine experience

SURROUNDINGS

Facilities