Palazzo Massaini – Le Scuderie

Hotel Description

You know, I’ve stayed in plenty of converted historic buildings across Tuscany, but Palazzo Massaini actually gets it right. This place sits right in the heart of Pienza – and I mean literally in the heart, not some marketing speak version of “centrally located.” You’re steps from Corso il Rossellino, the main pedestrian street that Pope Pius II designed back in the 1400s, which honestly makes every morning coffee run feel a bit theatrical.

The “Le Scuderie” part of the name gives it away – these used to be the palace stables, and they’ve done something really thoughtful with the conversion. The rooms have these gorgeous barrel-vaulted ceilings, but they’ve managed to make them feel cozy rather than cavernous (which, let’s be honest, a lot of these historic conversions get wrong). The stone walls are the real deal – thick enough that you won’t hear your neighbors, and they keep things naturally cool even during those brutal July afternoons when the Val d’Orcia sun is absolutely relentless. I mean, the air conditioning works fine, but half the time you don’t even need it.

What really sold me on this place is how they handle the whole “palazzo” thing without being pretentious about it. The entrance courtyard has this lovely vine-covered pergola where you can actually sit with a glass of wine – they stock local Brunello and Vino Nobile, which makes sense since Montepulciano is just a twenty-minute drive. The staff knows their stuff too; they pointed me toward this tiny enoteca on Via dell’Amore that I never would have found otherwise. Check-in was refreshingly straightforward – none of that hovering, over-attentive service that makes you feel like you’re being managed. Parking can be a bit tricky since Pienza’s historic center is mostly pedestrian-only, but they’ve got arrangements with a lot just outside the walls that’s maybe a three-minute walk.

The location thing is pretty ideal if you’re planning to explore the area properly. You’re basically equidistant from Montalcino (for the Brunello tours) and Montepulciano (for the Vino Nobile cellars), and honestly, the drive through the cypress-lined hills is half the point anyway. But even if you just want to wander around Pienza itself, you’re positioned perfectly. The morning light hits the Palazzo Piccolomini facade just right from their breakfast terrace, and you can walk to the cathedral in about ninety seconds. That 9.3 rating doesn’t surprise me at all – it’s the kind of place that manages to feel both authentic and comfortable without trying too hard at either.

Rooms

• Superior King Room with 1 large double bed for 2 adults
• King Room with Balcony with 1 large double bed for 2 adults

Reviews

• Nada from Croatia (10/10)

  Francesca from the reception was so kind and helpful, explained everything about the property.
  Rooms were new and very clean, properly designed for such a property.
  It was short but everything great.👍

• Hyony from South Korea (10/10)

  Super super beautiful place I have ever been in my life.. rooms were super clean, and beautiful, bathroom was really clean and beautiful … people were really kind and nice.. The breakfast place was really beautiful and food were really deliciouse especially coffee (moroccino) they made everymorning, the location was 8min by car from Pienza . The scenery from Palazzo Massaini was really beautiful .. It was Great experience staying in palazo massaini, I would like to stay again when I come to Toscany 🇮🇹

• Mihai from Romania (10/10)

  very friendly staff and warm welcome
  located on a hill allowing us to admire the wonderful Tuscan landscape from our room window
  room is very large and nice decorate with focus on every single detail
  excelent breaksfast , most probably the best we have had in similar type accomodation
  congratulations !

• Tamar from Israel (8/10)

  The wonderful building, the beautiful and comfortable room and the amazing view

• Aaron from Peru (9/10)

  Beautiful property with lots of parking space. Staff was very friendly, we were welcomed with a glass of wine during check-in. The breakfast and the pool were amazing, but you have to drive for 3 minutes: the property is part of a 3-hotel complex so you will have to go to another one of the hotels for those. Perfect location to visit Pienza, Montepulciano and Montalcino.

• Karen from United States (10/10)

  Unique experience staying in an 800 year old castle but in a newly refurbished modern room

• Alina from United Kingdom (10/10)

  I can't praise this place enough, the pictures barely do it justice.
  The staff are amazing, very frindly and attentive.
  Room is spotless and bed was very comfortable.
  Breakfast is delicious, freshly prepared with plenty of choice.

• Maija from Canada (10/10)

  Everything was amazing!

• Taiwei from Taiwan (10/10)

  Sit at the hill with excellent view and historic building but innovative interiors.
  Great service and tranquil place to unwind.

• Gisele from New Zealand (10/10)

  Stunning magical Property. On arrival you pass many tourists on the road taking photos of it as it is so beautiful.
  Very luxury break in Tuscany surrounded by stunning countryside and views.
  Excellent friendly service – requests for some extra amenities were dealt with immediately. Nothing was an issue. Very generous complimentary wine tasting was provided and the wines were all excellent.
  Wonderful luxurious bedroom suite overlooking the gardens and the views / perfect bed pillows etc. – in fact everything was perfect! The breakfast was unparalleled both in the very high standard and variety. It included a diverse range of unusual vegetable dishes which was a welcome relief from the usual breakfasts and even some top quality apricot juice plus the best coffee and even some traditional dessert wine to accompany the home baked cakes which were excellent.

SURROUNDINGS

Facilities