Very Good 740 Reviews
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What We Love

  • Some of the best views in Tuscany

  • Beautiful terraced gardens
  • Inventive on-site restaurant

  • Original details, like frescoes in the rooms

  • Inside one of the most beautiful towns in Italy
  • Free WiFi in the common areas only

What To Know

  • Certain amenities, like the bathrooms, are in need of a serious upgrade

  • No spa or gym on-site

  • Tends to attract families, particularly in the summer, so be prepared for kids

  • The outdoor pool is closed in the winter
  • Check-out is at 11 a.m.
  • Pets are permitted for no additional cost


  •  Free WiFi
  •  Handicap Accessible
  •  Pet-friendly
  •  Pool
  •  Restaurant
Disclaimer: This content was accurate at the time the hotel was reviewed. Please check our partner sites when booking to verify that details are still correct.
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The Review

There’s Tuscany, and then there’s iconic Tuscany. Rows of cypress trees and winding roads weaving their way up rolling green hillsides? You won’t find that in Chianti. Textbook Tuscany is the Val d’Orcia, a triangle southeast of Siena. Pienza is one of the Renaissance towns that dust the area’s hilltops (it’s not for nothing that both Pienza and the Val d’Orcia as a whole are UNESCO World Heritage Sites); and while it’s crawling with visitors in summer, right now, you’ll practically have it to yourself.

{“type”:”img-inline”,”src”:”/static/images/product/properties/1586/prop-94071-1314225893-full.jpg”,”width”:”275″,”caption”:”This romantic escape is an easy weekend trip, and a world away, from Florence and Rome.”}In an idyllic location in the heart of the tiny town, the hotel’s 15th-century cloisters invite passing tourists to stop for a photograph; inside, the public spaces are dressed with upholstered sofas and heavy rugs. The 37 rooms vary in size and style, and although some are in need of an upgrade (the showers feel more like closets, and rooms can feel a little gloomy in winter), I loved the evocative period details, like frescoed ceilings, vaults and arched ceilings.

But this is a place you visit for the location rather than the rooms. Outside is a series of terraced gardens, with views of the rolling Val d’Orcia hills and the dormant volcano Monte Amiata looming behind them. In summer, guests lounge by the swimming pool and meet for a pre-dinner aperitivo in the outdoor restaurant. In winter, pop on a coat and enjoy the spectacular view of hills unfolding below Pienza. Even breakfast — a spread of fresh eggs, cheese, jams, bread and pastries, in a bright room overlooking the gardens — is an unforgettable experience.

Away from the hotel, stop into the shops filled with pecorino cheese (a local speciality) or walk through Pienza’s main square, which was transformed into a model of Renaissance architecture by Pope Pius II in the 15th century — one of Renaissance Italy’s first examples of town planning. For a different view of Pienza’s rolling countryside, wander Via del Casello along the city walls and stop for a drink at a local cafe.

How to Get There

Hotel Relais II Chiostro di Pienza
Corso Rossellino 26
Pienza, 53026 Italy


Classic Villa turned hotel

Very central location and lovely old building. You feel connected to the past just walking in the Courtyard towards reception doors. There is a certain charm to be associated with the worn stair steps. They slope unnaturally downwards as you ascend so hold on to the rail! We had a small suite on the corner of the second floor. The View was incredible. Two steps from the sitting area went down to the bed and bathroom. They were quite steep to manage. Th bathroom maybe I could describe as first generation refit needing a second! The suite was comfortable but not 5 star.
We had breakfast there which was the typical European buffet - adequate but not outstanding. Order your coffee rather than help yourself to the Americano in the urn if you want a fresh, and hot, cup. You can choose to sit inside but if it is warm enough enjoy the terrace overlooking the valley. Service was very professional and reception very helpful.
The location couldn’t be better for exploring this charming part of Tuscany


This is a pleasant and quiet hotel. Our room was a comfortable size with a view over Tuscany. A good shower, AC, helpful staff. Nice breakfast buffet on the terrace.
Centrally located in an old monastery.

Stylish and friendly

Our first visit to ll Chiostro is unlikely to be our last. To be able to stay in such an elegant casa within a stonesthrow of the cathedral square in Pienza is a privilege indeed. The building is beautiful, the rooms are clean, the welcome is friendly and the view over the Val d’Orcia is unsurpassable. Thank you for an elegant sojourn. Next time we will stay longer and make sure to enjoy the delights of the restaurant.