Palazzo Massaini – La Pieve

Hotel Description

Look, I’ve stayed in plenty of converted historic buildings across Tuscany, but Palazzo Massaini actually gets it right. This 4-star gem sits just outside Pienza proper – you know, that perfect Renaissance town that UNESCO loves so much – and honestly, being a short walk from the main drag instead of right in the thick of it works in your favor. You get the medieval charm without tour groups chattering outside your window at 7 AM.

The building itself is this gorgeous stone palazzo that feels authentically lived-in rather than museum-perfect. I mean, the restoration work is impeccable, but they’ve kept all the character – thick walls that keep things naturally cool (crucial in summer), original terracotta floors that have this wonderful worn patina, and these deep-set windows that frame the Val d’Orcia views like paintings. Speaking of views, request a room facing south if you can. The rolling hills with their cypress-lined roads and golden wheat fields… it’s basically the Tuscany screensaver come to life. The staff – mostly locals who actually know the area – were genuinely helpful without being overly formal. They pointed me toward this little enoteca in town that I never would’ve found otherwise.

What really impressed me was how they’ve balanced historic preservation with modern comfort. The rooms have proper AC (not always a given in these old buildings), excellent WiFi, and bathrooms that don’t require contortionist skills to navigate. Breakfast gets served in this vaulted room that probably housed livestock centuries ago, and they source ingredients locally – the pecorino comes from farms you can literally see from the terrace. The pool area is tastefully tucked away so it doesn’t clash with the historic architecture, and there’s actually decent parking, which anyone who’s driven rental cars through Italian hill towns will appreciate.

You’re perfectly positioned here for exploring the Val d’Orcia – Montalcino is maybe twenty minutes away, and if you’re into wine (I mean, you’re in Tuscany), you can easily hit the Brunello producers. Pienza itself is walkable in an hour, but you’ll want to linger for the cheese shops and that incredible view from the town walls. The hotel’s location means you miss the day-tripper crowds but still get that authentic small-town Italian experience. With a 9.3 rating, they’re clearly doing something right, and after spending three nights there, I can see why people keep coming back.

Rooms

• Estimated price from: $221. Double or Twin Room with 1 large double bed for Max persons: 2
• Estimated price from: $280. Deluxe Double Room with 1 double bed for Max persons: 2
• Estimated price from: $280. Large Double Room with 1 large double bed for Max persons: 2
• Estimated price from: $287. Deluxe Room with 1 large double bed for Max persons: 2
• Estimated price from: $360. Deluxe Junior Suite with 1 large double bed and 1 sofa bed for Max persons: 2

Reviews

• Exceptional – Marzia from Italy – 13 July 2025 (10/10)

  Location, staff e atmosfera assolutamente all’altezza delle aspettative!

• Superb – Anna from Sweden – 5 July 2025 (9/10)

  Excellent location with a stunning view. Nice clean rooms. The staff at la Pieve were amazing and served a delicious breakfast. Nice pool area.
  
  What could be improved: No small fridge in the room, would have been nice to use for cooling water. No food serving except for breakfast.

• Exceptional – Federica from Italy – 22 June 2025 (10/10)

  We booked last minute and I’m so glad I discovered this place!!! The venue is beautiful, the staff is super lovely and welcoming, also the pool area is stunning and perfect for relaxing a little bit after visiting the small towns nearby. Breakfast is delicious, with an amazing view of the valleys!! Highly recommend 🙂
  
  What could be improved: Nothing

• Once in a lifetime place in Pienza! Highly recommend! – Heather from United States – 3 December 2024 (10/10)

  I felt very special staying at Massaini. The staff was wonderful and did everything possible to make my stay enjoyable. They went above and beyond in every way. I LOVED the property, it is simply beautiful!
  
  What could be improved: Nothing

• Exceptional – Tereza from Netherlands – 28 October 2024 (10/10)

  Amazing. The location is absolutely beautiful, cosy and very clean rooms, very noce and helpful staff and super delicious breakfast!

• Exceptional – Marios from Greece – 19 October 2024 (10/10)

  Everything was great! Very serene, very beautiful scenery, the breakfast was very good. The room was great very spacious, as well the bathroom! I hope i will come back one day!

• Exceptional – Briellen from Australia – 13 October 2024 (10/10)

  Stunning view, amazing breakfast

• It was picturesque, rustic, peaceful, clean and historic. – Elise from United States – 11 October 2024 (10/10)

  Breakfast was wonderful. In addition to made to order eggs and coffee "Americano"/cappuccino, we had freshly made vegetables, bakery, cold cuts and more. The area where breakfast was served was modern and clean and outdoor seating by the patio overlooked the valley.

• wonderful will definitely stay again – Elizabeth from United Kingdom – 31 August 2024 (10/10)

  views staff wonderful breakfast wine
  
  What could be improved: It would have been lovely if the pool had been heated.

• The most perfect stay in Val D’orcia – Tom from Australia – 8 August 2024 (10/10)

  This property was just fantastic. Awesome breakfast, gorgeous pool, big and spacious rooms and courtyard, very private and easily accessible. Just so beautiful and peaceful.

SURROUNDINGS

Facilities