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Our top choices for Pienza historic hotels

Interior
Antico Granaione

Antico Granaione

Antico Granaione
Rapolano Terme
9.8 out of 10, Exceptional, (59)
"old fashion building, clean and affordable"
United States
Irene
Antico Granaione
Front of property
Hotel Italia

Hotel Italia

Hotel Italia
3.0 star property
Cortona Old Town
9.0 out of 10, Wonderful, (287)
"The hotel amenities, comfort, hospitality are top notch. Should easily be a 4-star hotel! "
United Kingdom
Neha
Hotel Italia
Lobby
Residenza Fabroni

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (94)
"gorgeous historical property, very attentive host, great location"
United States
Sarah
The price is 2.306.461 ₫
2.660.770 ₫ total
includes taxes & fees
13 Jan - 14 Jan 2026
Residenza Fabroni
Sauna, hot tub, steam room, massages
Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa
5.0 star property
Cortona Old Town
10.0 out of 10, Exceptional, (254)
"Excellent hotel Staff very knowledgeable and friendly Loved everything about our stay and will return. "
Canada
Florence and Robert
The price is 7.975.888 ₫
8.897.265 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Monastero di Cortona Hotel & Spa
Single Room, 1 Single Bed, Private Bathroom, City View | View from room
B&B San Francesco

B&B San Francesco

B&B San Francesco
Cortona Old Town
8.8 out of 10, Excellent, (55)
"The B&B is charming, the location is perfect, and Beatrice and the staff are so nice!"
United States
Maria
B&B San Francesco
55-inch Smart TV with satellite channels, TV, Netflix
Palazzo Carletti

Palazzo Carletti

Palazzo Carletti
Montepulciano
9.8 out of 10, Exceptional, (241)
"Excelente hotel."
Mexico
jorge
Palazzo Carletti
2 outdoor pools, open 8:30 AM to 6:30 PM, pool umbrellas, pool loungers
Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel
5.0 star property
Montalcino
10.0 out of 10, Exceptional, (69)
"Wonderful stay "
United States
Talib
The price is 36.208.001 ₫
40.138.271 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Castiglion del Bosco, A Rosewood Hotel
Exterior
Castello di Gargonza

Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.2 out of 10, Wonderful, (39)
"All of the hotel staff did an outstanding job. Our room had everything we needed and the restaurant was great. Breakfast was exceptional. Special shoutout to Neri, the owner, for taking such good care of us. "
United States
Diane
Castello di Gargonza
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Pienza Hotel Reviews

Frequently asked questions

What can I expect on my historical trip to Pienza?
The historical places in Pienza are likely at the top of your travel itinerary. While you're visiting this quaint area, why not also enjoy all you'll find to see and do here?
How many historically relevant hotels are located in Pienza?
Pienza has 185 hotels and other lodging options bookable on Expedia, including 2 historic hotels or hotels close to historic sites.
What are the most important historical places and other sights to visit in Pienza?
Pienza is notable for landmarks like Palazzo Piccolomini, Historic Centre of Pienza and Pienza Cathedral. Cultural venues include Palazzo Borgia, Artemisia Gallery and Art Studio di Adelina Quadri. A couple of additional sights to add to your itinerary are Val di Chiana and Piazza Pio II.
What is a historic hotel like in Pienza?
Guests who choose historic hotels have a chance to stay in a building recognised with a national historic designation. Historic hotels throughout the world have had many former lives and uses, such as castles, stately homes, palaces or even pubs, lodges, old police stations or skyscrapers — any building that's been identified as being of special interest. These types of hotels in Pienza often preserve original characteristics such as period features or traditional architecture in their communal spaces or guestrooms.
What is the difference between a historic hotel and a heritage hotel?
The two are similar. The term "historic hotel" is more common in the U.S., while "heritage hotel" is often used in Asia and Europe. Historic hotels tend to focus on the building and architecture itself. A heritage hotel draws meaning mainly from the cultural value that the place has and how it shaped the community.
Do historic hotels in Pienza have modern facilities?
Yes, efforts are made to preserve treasured traditions and historic facades, but hotel interiors are fitted with modern conveniences and safety features. Tourists who book a stay should expect the popular amenities you'd get from a hotel such as WiFi, heating and air conditioning, and updated bathroom facilities. Booking a historic hotel in Pienza doesn't mean you will stay in a place that's rundown.