The Best Hotels in Pienza, Italy

Enjoy cloister views with a stay at the Relais Il Chiostro di Pienza
Enjoy cloister views with a stay at the Relais Il Chiostro di Pienza | Courtesy of Relais Il Chiostro di Pienza / Expedia
Nick Dauk

This pretty Tuscan hilltop town, once the summer residence of Pope Pius II, will embrace you with its narrow lanes flanked by stunning architecture. Before you know it, you’ll have a preferred honey and pecorino cheese combo from a local artisan whom you’ve come to know like an old friend. Discover why this Tuscan village in Italy is the ideal town for any type of traveller by staying at the best hotels in Pienza – bookable with Culture Trip.

1. La Bandita Townhouse

Guesthouse, Hotel

La Bandita Townhouse
Courtesy of La Bandita Townhouse /

Though La Bandita also offers a tranquil home in the Tuscan countryside, you’d be missing out on one of the overlooked elements of Tuscany: village life. Sleep right in Pienza’s historic centre and spend your days wandering cobblestone alleys taking in the Renaissance architecture. Watch the locals meander in and out of the main piazza, their arms full of fresh groceries – the same ingredients that the chef at the Townhouse Caffe will use for your daily meals.

2. Hotel Residence San Gregorio


Hotel Residence San Gregorio
Courtesy of Hotel Residence San Gregorioi / Expedia

Trade the backpack on your shoulders for a glass of wine in your hand at Pienza’s Hotel Residence San Gregorio. View the “ideal Renaissance city” from your pet-friendly suite and venture into the Val d’Orcia with your furry companion by your side. When you’ve worked up an appetite, La Piazzetta restaurant’s traditional Tuscan dishes will nourish your body and soul. The aromas of Pienza pecorino cheese, ribollita and pici with Tuscan ragù can only be rivalled by their flavours, which are undeniably Tuscany.

3. Piccolo Hotel La Valle


Piccolo Hotel La Valle
Courtesy of Piccolo Hotel La Valle / Expedia

Explore Pienza at your leisure from Piccolo Hotel La Valle. Within a few minutes, you can reach the Museo Diocesano, Pienza Cathedral and Palazzo Piccolomini’s Italian Renaissance Garden at a slow pace. You’ll have all day to spend embracing the historic sites – that is, if you don’t get too distracted staring off into the Val d’Orcia from your suite’s panoramic balcony. The breakfast buffet at this hotel in Pienza may derail your departure as well, but, thankfully, the Piazza Pio II and scenic point from The Gladiator aren’t going anywhere.

4. Relais Il Chiostro di Pienza


Relais Il Chiostro di Pienza
Courtesy of Relais Il Chiostro di Pienza / Expedia

This former 13th-century Franciscan convent is yours for however long you wish. The Relais Il Chiostro offers modern comforts in this magnificent hamlet. The rooms at this Pienza hotel grant you views of the cloister, the Val d’Orcia hills and historic centre streets, making you stop to wonder how rooms like the “classic” and “economy” could offer such picturesque perspectives at such affordable rates. Your friends will be envious when you show them photos of you lounging poolside in the remarkable Chiostro.

5. Hotel Corsignano


Hotel Corsignano
Courtesy of Hotel Corsignano / Expedia

As you soak in the terrace jacuzzi of Hotel Corsignano in Pienza, gazing out at the mature crop fields and cypress trees, you’ll wonder how anyone could ever leave. Wine on the solarium, negronis at the bar and a few adult indulgences in your superior suite will intoxicate you with Tuscan bliss. Your heart and head will be as bubbly and full as your stomach after a night dining on Chianina beef, pecorino cheese and Cinta Senese pork at the hotel’s restaurant.

6. Hotel Rutiliano Centro Benessere

Hotel, Spa Hotel

Hotel Rutiliano Centro Benessere
Courtesy of Hotel Rutiliano Centro Benessere / Expedia

A spa holiday in Tuscany – need we say more? Hotel Rutiliano Centro Benessere is well prepared to pamper you in their Wellness Center. A hammam bath and Finnish sauna wait for you as you let their masseuse work away every knot and stress in your body. Exhale your negative energy and inhale the clean air of the curate’s garden before retiring back to your double room for a midday nap. When you awake, you’ll find a bowl of stewed wild boar and a glass of local red ready for you at La Combriccola across the street.

7. Relais La Saracina


A rustic yet modern guest room with canopied bed and soft sofa both dressed in crinkly linens with two raffia lampshades hanging over the room at Relais La Saracina
Courtesy of Relais La Saracina / Expedia

Romantically concealed behind old cypress trees and aromatic gardens, the boutique Relais La Saracina is a rustic hotel a few kilometres east of Pienza with a fairytale-like ambience. Hide away in one of six secluded rooms, each lit by candlelight and enchanted by silence. And leave behind the vaulted ceilings, open beams and dusted walls only to follow the scent of breakfast – freshly baked bread and roasted coffee waits for you at a table beneath the ancient trees.

8. A440 in Tuscany


A440 in Tuscany
Courtesy of A440 in Tuscany / Expedia

An appreciation for the natural world will make your stay at A440 in Tuscany even more memorable. Geothermal heating and cooling, decor and furnishings constructed with natural materials and an organically filtered swimming pool are just three of the many ways A440 shows its love and reverence for the region. Let your hosts help you find the same admiration for Pienza with guided horse riding, hiking, cycling or walking tour through the neighbouring villages.

9. Castello di Spedaletto

Hotel, Villa

The entrance to Castello di Spedaletto with a pretty landscaped lawn either side of the path that leads to the front door.
Courtesy of Castello di Spedaletto / Expedia

Dreaming of afternoons spent in a Tuscan villa? Dream bigger at the stunning Castello di Spedaletto. This 12th-century castle turned hotel near Pienza has been transformed into a holiday farmhouse where serenity awaits. There are only three guest rooms, granting you a regal and reserved stay with meals prepared from the farm’s fresh ingredients. Explore the grounds and you’ll discover a number of tranquil gardens, where you can enjoy the same countryside views that visitors have cherished for nearly a millennium.

Culture Trips launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes places and communities so special.

Our immersive trips, led by Local Insiders, are once-in-a-lifetime experiences and an invitation to travel the world with like-minded explorers. Our Travel Experts are on hand to help you make perfect memories. All our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.

All our travel guides are curated by the Culture Trip team working in tandem with local experts. From unique experiences to essential tips on how to make the most of your future travels, we’ve got you covered.

Edit article