A historic square with a prominent tower and statues.

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Check availability on Pienza 5 Star Hotels

Tonight
Sep 22 - Sep 23
Tomorrow
Sep 23 - Sep 24
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

Our top choices for Pienza 5-star hotels

A stone building with a pool overlooking a mountainous landscape.
A dining area with a table and chairs, a vase with flowers, and a view of the countryside through an arched window.
A terrace with stone walls, potted plants, and outdoor furniture overlooking a valley with a river and distant hills during sunset.

1. Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery
Montalcino
United States
Juan
$761 nightly
$849 total
Oct 23 - Oct 24
Total with taxes and fees
Castello di Velona Resort Thermal SPA & Winery
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a stone building in the background.
A large estate with a swimming pool, surrounded by lush greenery and hills.
A buffet with various food items, a vase of flowers, and a mirror reflecting the room.
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 Kingdom
Rushab
$647 nightly
$721 total
Oct 10 - Oct 11
Total with taxes and fees
Villa di Piazzano - Small Luxury Hotel of the World
An aerial view of a large estate with multiple buildings, a swimming pool, and well-maintained gardens.
A spacious dining area with high ceilings and ornate ceiling decorations, featuring multiple tables set for dining.
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 large estate with multiple buildings, a swimming pool, and expansive green fields.

3. Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala
Montepulciano
United States
Mark
$515 nightly
$573 total
Sep 30 - Oct 1
Total with taxes and fees
Precise Tale Poggio Alla Sala
A stone-walled room with a large arched doorway, a sofa, a table with a vase, and a view of the landscape.
An open archway leading to a kitchen with a wooden ceiling, a hanging lantern, and a tiled backsplash.
A villa with a swimming pool, surrounded by lush greenery and a view of distant hills.
An outdoor dining area with tables and chairs, large windows, and a view of the surrounding landscape.

4. Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel
Montalcino
United Kingdom
Abdel
$2,345 nightly
$2,591 total
Oct 8 - Oct 9
Total with taxes and fees
Castiglion del Bosco, A Rosewood Hotel
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.

5. Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa
Cortona Old Town
United States
Gennadiy
$360 nightly
$405 total
Oct 11 - Oct 12
Total with taxes and fees
Monastero di Cortona Hotel & Spa
A woman relaxing by a pool with a historic building in the background.
A two-story building with a symmetrical facade, surrounded by lush greenery and a well-maintained hedge.
A bar area with a bartender preparing a drink, a well-stocked bar with various bottles, and a television in the background.
A modern bedroom with a large bed, a sofa, and two nightstands.

6. Fonteverde Thermal Spa Resort Tuscany

Fonteverde Thermal Spa Resort Tuscany
San Casciano dei Bagni
United States
Susan and Larry
$370 nightly
$411 total
Sep 23 - Sep 24
Total with taxes and fees
Fonteverde Thermal Spa Resort Tuscany
A pool with a modern water feature and a stone structure.
An indoor swimming pool with clear glass walls, a tiled floor, and a stone wall with a mosaic pattern.
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.

7. Mercure Petriolo Siena Terme Spa Hotel

Mercure Petriolo Siena Terme Spa Hotel
Civitella Paganico
United States
Mike
$86 nightly
$95 total
Sep 23 - Sep 24
Total with taxes and fees
Mercure Petriolo Siena Terme Spa Hotel
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.

8. Il Falconiere - Relais e Chateaux

Il Falconiere - Relais e Chateaux
Cortona
United States
Qingwen
$443 nightly
$497 total
Oct 22 - Oct 23
Total with taxes and fees
Il Falconiere - Relais e Chateaux
A courtyard with a stone building featuring a bell tower, outdoor seating, and greenery.
A hotel room with a large bed, a vanity with a mirror, and a green archway.
A covered outdoor seating area with a pool in the background.
A courtyard with a bell tower, a well-maintained lawn, and outdoor seating.

9. Hotel Certosa Di Maggiano

Hotel Certosa Di Maggiano
Siena
United States
Tulsi
$534 nightly
$598 total
Oct 22 - Oct 23
Total with taxes and fees
Hotel Certosa Di Maggiano
A large estate with multiple buildings, a swimming pool, and expansive green fields.
A restaurant with brick arches, white tablecloths, and floral centerpieces.
A swimming pool with a view of a hilly landscape, surrounded by trees and grass.
A balcony with a view of a green landscape and a body of water.

10. Borgo Sant'Ambrogio Resort

Borgo Sant'Ambrogio Resort
Trequanda
United States
María
$175 nightly
$196 total
Oct 18 - Oct 19
Total with taxes and fees
Borgo Sant'Ambrogio Resort
A pool with a tree in the center, surrounded by a deck and a view of hills in the background.
A table set for dining with a scenic view of hills in the background.

11. La Posta Hotel & Thermal Spa

La Posta Hotel & Thermal Spa
San Quirico d'Orcia
United States
Anna
$416 nightly
$463 total
Oct 21 - Oct 22
Total with taxes and fees
La Posta Hotel & Thermal Spa
A swimming pool with lounge chairs and a person in a patterned dress.
An indoor dining area with tables set for meals, stone walls, and hanging light fixtures.
A stone staircase with candles and a sign reading "CANTINA".
A stone building with a swimming pool, surrounded by a well-maintained garden and a clear sky.

12. Castel Monastero - The Leading Hotels of the World

Castel Monastero - The Leading Hotels of the World
Castelnuovo Berardenga
United Kingdom
G
$569 nightly
$638 total
Oct 23 - Oct 24
Total with taxes and fees
Castel Monastero - The Leading Hotels of the World
A couple in a hot spring with a large rock formation in the background.
A room with large windows offering a view of a garden with a yoga mat and a white cushion on the floor.
A restaurant with a bar area, dining tables, and chairs, with a view of the outdoors.
A person in a white robe standing in a bamboo garden.

13. ADLER Thermae

ADLER Thermae
San Quirico d'Orcia
United Kingdom
Abdel
$811 nightly
$898 total
Sep 23 - Sep 24
Total with taxes and fees
ADLER Thermae
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.

14. Relais La Corte dei Papi

Relais La Corte dei Papi
Cortona
United Kingdom
Frithjof
$383 nightly
$430 total
Sep 29 - Sep 30
Total with taxes and fees
Relais La Corte dei Papi
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 courtyard with stone buildings, potted plants, and outdoor seating.
A large stone castle with multiple towers, surrounded by vineyards and cypress trees.

15. Castello Banfi - Il Borgo - Relais et Chateaux

Castello Banfi - Il Borgo - Relais et Chateaux
Montalcino
United States
Jason
$1,317 nightly
$1,460 total
Oct 22 - Oct 23
Total with taxes and fees
Castello Banfi - Il Borgo - Relais et Chateaux
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 cozy living room with a fireplace, a clock, and a sofa.
An open doorway leading to a living room with a sofa, a coffee table, and a lamp.

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 restaurant with brick arches, wooden tables, and a piano.
A view of a countryside landscape with rolling hills, a swimming pool, and a building with a tiled roof.
A swimming pool with lounge chairs and umbrellas, surrounded by a stone building with multiple windows.

18. Agriturismo San Fabiano

Agriturismo San Fabiano
Monteroni d'Arbia
United States
James
Agriturismo San Fabiano
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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
$181 nightly
$206 total
Oct 19 - Oct 20
Total with taxes and fees
Hotel Corsignano
Castello di Leonina Relais

Castello di Leonina Relais

Strada Di Leonina 5 Asciano SI
$148 nightly
$170 total
Oct 19 - Oct 20
Total with taxes and fees
9/10 Wonderful! (153 reviews)
Castello di Leonina Relais
Grand Hotel Milano

Grand Hotel Milano

Viale Roma, 46 Chianciano Terme SI
$87 nightly
$100 total
Sep 29 - Sep 30
Total with taxes and fees
8/10 Very Good! (55 reviews)
Grand Hotel Milano
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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

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"Service was top notch and Claudio at the bar made the best cocktails"
Alexander 2-night trip
Posted 5 hours ago
Monastero di Cortona Hotel & Spa
Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

10/10 Excellent
"We enjoyed this picturesque hotel for a night of R&R. We especially liked arranging for e bikes to be delivered and taking the back gravel roads to look around. The second day we ran the same route."
Justine 1-night trip
Posted 6 hours ago
Precise Tale Poggio Alla Sala
Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

10/10 Excellent
"Stunning little hotel with the most beautiful setting, gardens and pool. The room was exceptionally appointed clean. The best part of the stay was the restaurant. The best meals we had on our entire trip. Definitely recommend hiring e-bikes and riding up to Cortona!"
Beren 2-night trip
Posted 2 days ago
Villa di Piazzano - Small Luxury Hotel of the World
Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

10/10 Excellent
"Very warm and friendly service."
Abdel 2-night trip
Posted 9 days ago
Castiglion del Bosco, A Rosewood Hotel

Find out more about Pienza

Why not request the best during your jaunt to Pienza? After all, you love the finer things in life, both at home and when you book a getaway. You'll join the multitudes of vacationers who have made Pienza so popular in the last year. There's no reason to delay a getaway to Pienza any longer. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. Our 5-star hotels in Pienza are the perfect places to relax in during your next escape. Don't wait any longer!

Get a Great Deal on 5-Star Hotels in Pienza

You'll have a fantastic time at one of these 5-star hotels. Excellent service, delicious meals, and attentive guest service are all at your fingertips. You're sure to find exactly the accommodation you need. You can also look forward to an outstanding experience and fantastic customer care, so get ready for a wonderful adventure. How do you want to relax? A full-body massage to help your cares fall away? A concierge to help you suggest the next attraction to visit? High thread-count sheets, lip-smacking main courses, and even a hot tub in the bathroom...these hotels will leave you amazed. Don't want to take our word for it? Explore our listings and pick the perfect accommodation for your needs.

You won't sleep and order room service the entire time, though. Don't worry. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what's on your agenda, the 5-star hotels in Pienza are waiting for you to relax after a busy day.

Your Getaway Starts Today

The results are in, and Pienza 5-star hotels are the place to be when you book your next vacation. If you've been dreaming about a vacation set here, then go ahead and book it. Expedia can help you land a great deal on accommodation. It's time to indulge yourself. Opt for one of Expedia's Pienza 5-star hotels today and decompress in complete comfort tomorrow.

Frequently asked questions

What are the best 5-star hotels in Pienza?
Offering superior amenities and services, Expedia travelers rate ADLER Spa Resort Thermae as one of the most popular 5-star hotels in Pienza. You'll be in the lap of luxury from the second you step foot into the lobby.
How much does it cost to stay in a 5-star hotel in Pienza?
The amount you pay for a 5-star hotel in Pienza depends on factors like when you want to go and the length of your trip. Our insider tip for bagging an awesome deal? Use our pricing filters to check out all of the available options for your selected dates.
  • Search for the lowest price per night from $100
What makes a hotel 5 stars in Pienza?
From fine dining venues and 24/7 fitness centers to swimming pools and luxury bedding, the 5-star experience in Pienza is all about luxury and relaxation. But it takes more than just upscale conveniences to earn a 5-star rating. Stays must also offer exceptional services like in-room massage treatments, on-site laundry and room service any time day or night.

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