A historic square with a prominent tower and statues.

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Check availability on Pienza 5 Star Hotels

Tonight
Sep 17 - Sep 18
Tomorrow
Sep 18 - Sep 19
This weekend
Sep 18 - Sep 20
Next weekend
Sep 25 - Sep 27

Our top choices for Pienza 5-star hotels

A stone building with a pool overlooking a mountainous landscape.
A terrace with stone walls, potted plants, and outdoor furniture overlooking a valley with a river and distant hills during sunset.
A dining area with a table and chairs, a vase with flowers, and a view of the countryside through an arched window.
A stone pathway leading to a gate with tall cypress trees on either side, illuminated by soft lighting.

1. Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery
Montalcino
United States
Song
$760 nightly
$847 total
Sep 27 - Sep 28
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.
An outdoor dining area with tables set for a meal, surrounded by greenery and trees.
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.

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

Villa di Piazzano - Small Luxury Hotel of the World
Cortona
United Kingdom
Rushab
$651 nightly
$725 total
Oct 12 - Oct 13
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 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.
A spacious dining area with high ceilings and ornate ceiling decorations, featuring multiple tables set for dining.

3. Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala
Montepulciano
United States
Mark
$531 nightly
$591 total
Oct 7 - Oct 8
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 aerial view of a villa with a swimming pool, terraced gardens, and a stone pathway.
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 historic town with traditional architecture, a central courtyard with a swimming pool, and a view of distant mountains.
A narrow hallway with a stone wall and a clock.
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
$358 nightly
$403 total
Sep 27 - Sep 28
Total with taxes and fees
Monastero di Cortona Hotel & Spa
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.

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.
A large, multi-story building with a swimming pool, surrounded by lush greenery.
An indoor swimming pool with clear glass walls, a tiled floor, and a stone wall with a mosaic pattern.
A buffet table with various desserts and a long dining area with tables and chairs.

7. Mercure Petriolo Siena Terme Spa Hotel

Mercure Petriolo Siena Terme Spa Hotel
Civitella Paganico
United States
Mike
$86 nightly
$95 total
Sep 21 - Sep 22
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 person in a swimming pool with a view of trees and mountains through a window.
A stone building with a red awning, potted plants, and a staircase leading to the entrance.

8. Il Falconiere - Relais e Chateaux

Il Falconiere - Relais e Chateaux
Cortona
United States
Qingwen
$531 nightly
$593 total
Oct 15 - Oct 16
Total with taxes and fees
Il Falconiere - Relais e Chateaux
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.
A room with two wooden chairs with floral upholstery, a wall-mounted artwork depicting a stylized landscape, and a wooden floor.

9. Hotel Certosa Di Maggiano

Hotel Certosa Di Maggiano
Siena
United States
Tulsi
$504 nightly
$566 total
Sep 22 - Sep 23
Total with taxes and fees
Hotel Certosa Di Maggiano
A large estate with multiple buildings, a swimming pool, and expansive green fields.
A balcony with a view of a green landscape and a body of water.
A swimming pool with a view of a hilly landscape, surrounded by trees and grass.
A dining area with brick walls, large windows, and a rustic stone ceiling. Tables are set with white tablecloths and candles.

10. Borgo Sant'Ambrogio Resort

Borgo Sant'Ambrogio Resort
Trequanda
United States
María
$150 nightly
$168 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
$464 nightly
$516 total
Oct 11 - Oct 12
Total with taxes and fees
La Posta Hotel & Thermal Spa
A swimming pool with lounge chairs and a person in a patterned dress.
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.
A person performing a yoga pose in a grassy area with a historic building in the background.

12. Castel Monastero - The Leading Hotels of the World

Castel Monastero - The Leading Hotels of the World
Castelnuovo Berardenga
United Kingdom
G
$561 nightly
$629 total
Oct 18 - Oct 19
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 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.

13. ADLER Thermae

ADLER Thermae
San Quirico d'Orcia
United Kingdom
Abdel
$811 nightly
$898 total
Oct 15 - Oct 16
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 historic stone building with arched doorways and a courtyard at twilight.
A modern bathroom with a large freestanding bathtub, a glass shower enclosure, and ornate mirrors.
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
$352 nightly
$396 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.
A large stone castle with multiple towers, surrounded by vineyards and cypress trees.
A stone building with a swimming pool, lounge chairs, and umbrellas.
A courtyard with stone buildings, potted plants, and outdoor seating.

15. Castello Banfi - Il Borgo - Relais et Chateaux

Castello Banfi - Il Borgo - Relais et Chateaux
Montalcino
United States
Jason
$1,386 nightly
$1,537 total
Oct 17 - Oct 18
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.
A large, historic building with multiple wings and a courtyard.

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
$196 nightly
$222 total
Oct 16 - Oct 17
Total with taxes and fees
9.4/10 Exceptional! (381 reviews)
Hotel Corsignano
Castello di Leonina Relais

Castello di Leonina Relais

Strada Di Leonina 5 Asciano SI
$147 nightly
$169 total
Oct 11 - Oct 12
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
$88 nightly
$101 total
Sep 30 - Oct 1
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
"The staff was so friendly from the moment we arrived. They guided us into the parking lot, assisted in booking dinner reservations and spa reservations. They were also extremely friendly throughout our stay, whether the bar, breakfast, dinner, and the cleaning staff. They also brought our luggage to our room and helped us at checkout. Overall an amazing experience. To note the breakfast was exceptional not a buffet. It was a sit down breakfast à la carte, coffee, fresh juices, omelettes made to order, and a 3 tier of pastries, fruits, and local meats and cheeses everyday. We loved our stay!! Also the room was very clean, they mopped the room as well!"
Julia 5-night trip
Posted 2 days ago
Monastero di Cortona Hotel & Spa
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 4 days ago
Castiglion del Bosco, A Rosewood Hotel
Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

8/10 Good
"Staying here was a wonderful and truly unique experience. The only reason I’m giving it 4 stars instead of 5 was because of the challenges we had with the air conditioning in our room. That said, the staff really did make an effort to find a workaround for us. While it wasn’t a perfect solution, it definitely helped, and we appreciated how responsive and accommodating they were. The hotel itself is an old castle, and that alone makes staying here such a special experience. The property is beautiful, incredibly charming, and very well maintained. You simply can’t replicate the character, history, and ambiance that come with staying in a property like this. The setting and surroundings are beautiful. It was definitely one of those experiences that felt uniquely Italian and added something special to our trip. My only recommendation would be to visit when the temperatures aren’t quite as hot. Given the age and historic nature of the property, I can appreciate that modernizing certain things like the air conditioning may not be as straightforward as it would be in a newer hotel. During cooler weather, I imagine our experience would have been close to perfect. Overall, we really enjoyed our stay and are glad we had the opportunity to experience such a beautiful and unique property. I would absolutely recommend it, just perhaps not during the hottest part of the summer!"
Ruth 3-night trip
Posted 8 days ago
Castello di Velona Resort Thermal SPA & Winery
Fonteverde Thermal Spa Resort Tuscany

Fonteverde Thermal Spa Resort Tuscany

10/10 Excellent
"Nice clean stay. Staff excellent"
Susan and Larry 3-night trip
Posted 12 days ago
Fonteverde Thermal Spa Resort Tuscany

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 $101
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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