A historic square with a prominent tower and statues.

Compare and book 5 Star hotels in Pienza, Tuscany

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Pienza 5 Star Hotels

Tonight
28 Aug - 29 Aug
Tomorrow
29 Aug - 30 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sept - 6 Sept

Our top choices for Pienza 5-star hotels

An aerial view of a large estate with multiple buildings, a swimming pool, and well-maintained gardens.
A cozy lounge area with a green sofa, a wooden coffee table, wicker chairs, and a view of a lush landscape through an arched doorway.
A spacious dining area with high ceilings and ornate ceiling decorations, featuring multiple tables set for dining.
A large estate with multiple buildings, a swimming pool, and expansive green fields.

1. Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala
Montepulciano
United States
Wilbert
£487
includes taxes & fees
31 Aug - 1 Sept
Precise Tale Poggio Alla Sala
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a stone building in the background.
A buffet with various food items, a vase of flowers, and a mirror reflecting the room.
A hallway with a checkered floor, arched windows, and a chandelier.
An outdoor dining area with tables set for a meal, surrounded by greenery and trees.

2. Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World
Cortona
United States
Niyome
£580
includes taxes & fees
4 Sept - 5 Sept
Villa di Piazzano - Small Luxury Hotel of the World
A gazebo with a glass enclosure, surrounded by potted plants and wicker furniture, overlooking a scenic landscape.
A person standing at the entrance of a building with a stone staircase leading up to a door.
A stone building with a red awning, potted plants, and a staircase leading to the entrance.
A person in a swimming pool with a view of trees and mountains through a window.

3. Il Falconiere - Relais e Chateaux

Il Falconiere - Relais e Chateaux
Cortona
United States
Marie
£490
includes taxes & fees
26 Sept - 27 Sept
Il Falconiere - Relais e Chateaux
A stone-walled room with a large arched doorway, a sofa, a table with a vase, and a view of the landscape.
An outdoor dining area with tables and chairs, large windows, and a view of the surrounding landscape.
An open archway leading to a kitchen with a wooden ceiling, a hanging lantern, and a tiled backsplash.

4. Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel
Montalcino
United States
Talib
£2,284
includes taxes & fees
27 Sept - 28 Sept
Castiglion del Bosco, A Rosewood Hotel
A woman relaxing by a pool with a historic building in the background.
A modern bedroom with a large bed, a sofa, and two nightstands.
A bar area with a bartender preparing a drink, a well-stocked bar with various bottles, and a television in the background.
A building with multiple balconies, outdoor seating with umbrellas, and a paved walkway.

5. Fonteverde Thermal Spa Resort Tuscany

Fonteverde Thermal Spa Resort Tuscany
San Casciano dei Bagni
United States
Hani
£307
includes taxes & fees
30 Aug - 31 Aug
Fonteverde Thermal Spa Resort Tuscany
A stone building with a pool overlooking a mountainous landscape.
A stone pathway leading to a gate with tall cypress trees on either side, illuminated by soft lighting.
A terrace with stone walls, potted plants, and outdoor furniture overlooking a valley with a river and distant hills during sunset.

6. Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery
Montalcino
United States
Song
£567
includes taxes & fees
27 Sept - 28 Sept
Castello di Velona Resort Thermal SPA & Winery
A terrace with sun loungers, stone walls, and potted plants.
A narrow hallway with a stone wall and a clock.
A pool area with lounge chairs, a hot tub, and a view of mountains.
A spacious lobby with a high ceiling, a grand chandelier, and a staircase leading to an upper level.

7. Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa
Cortona Old Town
United States
Gennadiy
£294
includes taxes & fees
13 Sept - 14 Sept
Monastero di Cortona Hotel & Spa
A pool with a tree in the center, surrounded by a deck and a view of hills in the background.
A bar area with green walls, wooden stools, and a bar counter.
A table set for dining with a scenic view of hills in the background.

8. La Posta Hotel & Thermal Spa

La Posta Hotel & Thermal Spa
San Quirico d'Orcia
United States
Anna
£346
includes taxes & fees
29 Aug - 30 Aug
La Posta Hotel & Thermal Spa
A pool with a modern water feature and a stone structure.
A large, multi-story building with a swimming pool, surrounded by lush greenery.
A wicker dining table set with breakfast items, a vase of flowers, and a scenic view.
An indoor swimming pool with clear glass walls, a tiled floor, and a stone wall with a mosaic pattern.

9. Mercure Petriolo Siena Terme Spa Hotel

Mercure Petriolo Siena Terme Spa Hotel
Civitella Paganico
United States
Mike
£71
includes taxes & fees
29 Aug - 30 Aug
Mercure Petriolo Siena Terme Spa Hotel
A stone wall with a view of rolling hills and mountains.
An outdoor dining area with tables and chairs, a flower arrangement, and a view of the countryside.
A stone building with a swimming pool, lounge chairs, and umbrellas.
A large stone castle with multiple towers, surrounded by vineyards and cypress trees.

10. Castello Banfi - Il Borgo - Relais et Chateaux

Castello Banfi - Il Borgo - Relais et Chateaux
Montalcino
United States
Jason
£1,226
includes taxes & fees
29 Aug - 30 Aug
Castello Banfi - Il Borgo - Relais et Chateaux
A couple in a hot spring with a large rock formation in the background.
A person in a white robe standing in a bamboo garden.
A restaurant with a bar area, dining tables, and chairs, with a view of the outdoors.
A hotel with a large building, a pool, and a landscaped garden.

11. ADLER Thermae

ADLER Thermae
San Quirico d'Orcia
United States
Nataliya
£671
includes taxes & fees
1 Sept - 2 Sept
ADLER Thermae
A large estate with multiple buildings, a swimming pool, and expansive green fields.
A swimming pool with a view of a hilly landscape, surrounded by trees and grass.
A restaurant with brick arches, white tablecloths, and floral centerpieces.
A balcony with a view of a green landscape and a body of water.

12. Borgo Sant'Ambrogio Resort

Borgo Sant'Ambrogio Resort
Trequanda
United States
María
£149
includes taxes & fees
22 Sept - 23 Sept
Borgo Sant'Ambrogio Resort
A bed with white bedding and a decorative headboard with a floral pattern.
A covered outdoor seating area with benches and tables, a pathway, and a view of a garden and pool.
A courtyard with a stone building featuring a bell tower, outdoor seating, and greenery.
An aerial view of a historic building with a central tower, surrounded by lush greenery and a swimming pool.

13. Hotel Certosa Di Maggiano

Hotel Certosa Di Maggiano
Siena
United States
Tulsi
£442
includes taxes & fees
7 Sept - 8 Sept
Hotel Certosa Di Maggiano
A swimming pool with lounge chairs and a person in a patterned dress.
A stone staircase with candles and a sign reading "CANTINA".
A courtyard with a swimming pool, stone buildings, and a lush green garden.
A person performing a yoga pose in a grassy area with a historic building in the background.

14. Castel Monastero - The Leading Hotels of the World

Castel Monastero - The Leading Hotels of the World
Castelnuovo Berardenga
United Kingdom
G
£504
includes taxes & fees
28 Sept - 29 Sept
Castel Monastero - The Leading Hotels of the World
A grand banquet hall with ornate ceiling, long tables set for a formal event, and elaborate floral centerpieces.
A modern bathroom with a large freestanding bathtub, a glass shower enclosure, and ornate mirrors.
A historic stone building with arched doorways and a courtyard at twilight.
A long banquet table with gold candelabras, white flowers, and gold tableware.

15. Relais La Corte dei Papi

Relais La Corte dei Papi
Cortona
United Kingdom
Frithjof
£322
includes taxes & fees
3 Sept - 4 Sept
Relais La Corte dei Papi
A stone villa with a swimming pool, outdoor seating, and a scenic sunset view.
An arched stone corridor leading to a room with a billiards table, a lamp, and a view of the outdoors.
A large, historic building with multiple wings and a courtyard.
A cozy living room with a fireplace, a clock, and a sofa.

16. Podere Cavalbianco

Podere Cavalbianco
Monte San Savino
United States
Edith
Podere Cavalbianco

17. Castel Porrona Relais & Spa

Castel Porrona Relais & Spa
Cinigiano
Finland
Joona
Castel Porrona Relais & Spa
A dining area with a long table set for breakfast, featuring bread, pastries, and fruit.
A view of a countryside landscape with rolling hills, a swimming pool, and a building with a tiled roof.
A cozy living area with wicker sofas, a coffee table, and a brick wall.
A restaurant with brick arches, wooden tables, and a piano.

18. Agriturismo San Fabiano

Agriturismo San Fabiano
Monteroni d'Arbia
United States
James
Agriturismo San Fabiano
Save an average of 15% on thousands of hotels when you're signed in

Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Pienza.
Hotel Corsignano

Hotel Corsignano

Via Della Madonnina 11 Pienza SI
£152
30 Aug - 31 Aug
includes taxes & fees
9.4/10 Exceptional! (376 reviews)
Hotel Corsignano
Castello di Leonina Relais

Castello di Leonina Relais

Strada Di Leonina 5 Asciano SI
£104
30 Aug - 31 Aug
includes taxes & fees
9/10 Wonderful! (148 reviews)
Castello di Leonina Relais
Grand Hotel Admiral Palace

Grand Hotel Admiral Palace

Via Umbria 2 Chianciano Terme SI
£92
17 Sept - 18 Sept
includes taxes & fees
8.2/10 Very good! (323 reviews)
Grand Hotel Admiral Palace
Still don't see what you're looking for?
See all properties in Pienza.
You can also use these popular filters to refine your search.
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.

Learn more about Pienza

The Renaissance town's perfectly preserved architecture frames spectacular views of Val d'Orcia from its ancient walls. Sample Pecorino cheese at small shops along cobblestone streets or join locals for aperitivo in Piazza Pio II.

See all hotels in Pienza
A historic square with a prominent tower and statues.

Top Pienza Hotel Reviews

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

10/10 Excellent
"Amazing! If you are a family visiting Tuscany I highly recommend"
Wilbert 2-night trip
Posted 23 hours ago
Precise Tale Poggio Alla Sala
Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"Amazing!!!! Very well kept place, the staff treats you like family. Room was cleaned fast in the morning. Restaurant and bar staff as well were amazing. The pool area is good vibes and the drinks and really good too 👍👍 I would definitely come back."
Daniele 7-night trip
Posted 6 days ago
Monastero di Cortona Hotel & Spa
Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

10/10 Excellent
"Staff was helpful , and the room was clean. The Antica Casina di Caccia dining with wine pairing was absolutely amazing. Also took some great pictures in the garden. The breakfast was nice too."
Yan Bo 1-night trip
Posted 10 days ago
Villa di Piazzano - Small Luxury Hotel of the World
Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent
"This property was amazing from the moment we booked. Chiara was extremely helpful with looking into horseback riding and other tours for us. I made a mistake in booking and she caught it and corrected it before we even arrived. She was great. Additionally, the room was beautiful and really clean. The food was delicious and every waitstaff that we encountered was polite and attentive--it could not have been a better experience."
Amy 2-night trip
Posted 2 weeks ago
Castello di Velona Resort Thermal SPA & Winery
Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

10/10 Excellent
"Best hotel ever."
Ray 2-night trip
Posted 1 month ago
Castiglion del Bosco, A Rosewood Hotel

Find out more about Pienza

Frequently asked questions

What are the best 5-star hotels in Pienza?
If you're seeking a 5-star experience, ADLER Spa Resort Thermae offers one of the best of them according to reviews by our customers. Book a room at this Pienza escape and you'll get the highest standard of service, upscale furnishings and top-notch facilities.
How much does it cost to stay in a 5-star hotel in Pienza?
There are a variety of pricing options for 5-star hotels in Pienza on Expedia. The amount you pay will depend on when you want to travel, length of stay and other factors. Compare available accommodation for your chosen dates and make use of our pricing and other filters to find the perfect upscale stay.
  • Search for the lowest price per night from £92
What makes a hotel 5 stars in Pienza?
In Pienza, a hotel needs to provide a certain level of upscale amenities to earn a 5-star rating. These may include gourmet restaurants, saunas and spas, on-site gyms, luxury toiletries, premium bedding and more. What also sets 5-star hotels apart is their guest-focused service. You'll enjoy things like in-room massages, nightly turn-down services and concierge services. Some may even offer additional touches such as welcome gifts.

Explore a world of travel with Expedia