Explore top 2026 5 Star Hotels in Pienza

Name: Castel Monastero - The Leading Hotels of the World
Price range: $522 total
Rating: 9

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Top Pienza 5 Star hotels

Villa di Piazzano - Small Luxury Hotel of the World

Localita Piazzano, C.P. 6 Cortona AR

$682 nightly

$759 total

Oct 23 - Oct 24

Total with taxes and fees

This hotel features an outdoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and airport ...

9.8/10 Exceptional! (257 reviews)

Reviewed on Oct 17, 2026

Castello di Velona Resort Thermal SPA & Winery

Località Velona Montalcino SI

Fully refundableReserve now, pay when you stay

$567 nightly

$635 total

Nov 15 - Nov 16

Total with taxes and fees

This luxury hotel features an attached winery, a full-service spa, and hot springs. Traveling on business? Take advantage of the free WiFi in public areas, express ...

9/10 Wonderful! (379 reviews)

"La vue est panoramique et le château est grandiose"

Reviewed on Oct 16, 2026

Fonteverde Thermal Spa Resort Tuscany

Localita Terme, 1 San Casciano dei Bagni SI

Fully refundableReserve now, pay when you stay

$300 nightly

$334 total

Nov 2 - Nov 3

Total with taxes and fees

This luxury hotel features a full-service spa, hot springs, and 2 restaurants. Families will appreciate the children's pool, onsite laundry facilities, and in-room ...

9.4/10 Exceptional! (221 reviews)

"Unbelievable view! And the rooms were very clean and large. I hope we get the opportunity to make it back to this hotel one day!"

Reviewed on Oct 20, 2026

Precise Tale Poggio Alla Sala

Via Di Poggio Alla Sala, 10 Montepulciano SI

A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Family-friendly amenities include a playground and in-room childcare. ...

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Castiglion del Bosco, A Rosewood Hotel

Localita Castiglion del Bosco Montalcino SI

Fully refundableReserve now, pay when you stay

$1,240 nightly

$1,375 total

Nov 3 - Nov 4

Total with taxes and fees

This luxury hotel features a golf course, an attached winery, and a full-service spa. There's fun for all ages with a children's club and an arcade/game room, ...

Monastero di Cortona Hotel & Spa

Via del Salvatore Cortona AR

Fully refundableReserve now, pay when you stay

$247 nightly

$276 total

Nov 8 - Nov 9

Total with taxes and fees

A full-service spa and an indoor pool are featured at this luxury hotel. Enjoy the hot tub and free perks like full breakfast and WiFi in public areas. You'll ...

10/10 Exceptional! (358 reviews)

"Amazing service and care. Especially Sara, Mathilda, Fredrico and Allesandro. The manager was so helpful as well. A must stay!"

Reviewed on Oct 20, 2026

Hotel Certosa Di Maggiano

Strada di Certosa, 82/86 Siena SI

$276 nightly

$310 total

Nov 17 - Nov 18

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. There's fun for all ages with a playground and an arcade/game room, and families will appreciate ...

Il Falconiere - Relais e Chateaux

Localita San Martino 370 Cortona AR

Fully refundableReserve now, pay when you stay

$368 nightly

$409 total

Nov 15 - Nov 16

Total with taxes and fees

An attached winery, a full-service spa, and 2 outdoor pools are all featured at this luxury hotel. Families will appreciate kid-friendly dining and in-room childcare, ...

Mercure Petriolo Siena Terme Spa Hotel

Strada Provinciale di Petriolo Civitella Paganico GR

Fully refundableReserve now, pay when you stay

$84 nightly

$95 total

Oct 26 - Oct 27

Total with taxes and fees

This luxury hotel features a full-service spa, hot springs, and 2 restaurants. Enjoy the 5 indoor pools and get free self parking. Make the most of the 24-hour ...

8.6/10 Excellent! (267 reviews)

"One other guest we meet called it the hotel from hell, which somes it up properly. A very strange vibe in this hotel a cross between a murder mystery hotel and a soviet area spa. The staff need to learn how to smile and serve it's customers properly, only the breakfast lady was great. Hotel difficult ..."

Reviewed on Oct 17, 2026

Castel Monastero - The Leading Hotels of the World

Monastero D'Ombrone Castelnuovo Berardenga SI

Fully refundableReserve now, pay when you stay

$464 nightly

$522 total

Nov 21 - Nov 22

Total with taxes and fees

A full-service spa, 2 restaurants, and 2 indoor pools are all featured at this luxury hotel. Traveling on business? Take advantage of the free WiFi in public ...

9/10 Wonderful! (147 reviews)

"Beautiful hotel, staff amazing, tranquil surroundings, and incredible food. The perfect stay in Tuscany!"

Reviewed on Sep 7, 2026

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Pienza Resorts & 5 Star Hotels

Looking for your own little slice of heaven during your next trip? Check out all the best 5-star hotels in Pienza to make sure your trip is as extravagantly comfortable as you expect.

Whether you plan on staying in your room the whole time or getting out and enjoying the city, you’ll be living the life while staying at your luxury accommodation. With so many amenities at your beck and call, you might try to turn your stay into a staycation!

Many of the 5-star hotels have award-winning restaurants you can dine at, as well as plush bedding and a concierge service to take care of your every need. Most also offer pools and modern fitness centers, not to mention high-speed Wi-Fi.

For your next trip, book a hotel that can be your own little hideaway, whether you’re in town for business or leisure. Pienza 5-star hotels provide you with all the comforts and amenities you expect from a sophisticated hotel, with a staff that’s happy to ensure you have everything you need to feel at home.

Whether you’re a first-time guest, or you’ve stayed in 5-star hotels in Pienza before, you’ll have no shortage of options to choose from on your next trip when you book with Travelocity. Browse our vast selection and find great deals on luxury lodging.

Recent Pienza hotel reviews by fellow wanderers

Fonteverde Thermal Spa Resort Tuscany

5 out of 5

Posted 11 hours ago

Travelocity Verified Review

"Unbelievable view! And the rooms were very clean and large. I hope we get the opportunity to make it back to this hotel one day!"

A verified traveler stayed at Fonteverde Thermal Spa Resort Tuscany

Villa di Piazzano - Small Luxury Hotel of the World

5 out of 5

Posted 4 days ago

Travelocity Verified Review

"This was an amazing stay recommended by a friend and we really loved this place. The only immediate issues were the A/C broke and the TV was hard to setup, and the toilet seat was cracked and broke when I sat on it. But they fixed all that on day 1 and we had an amazing time - staff was amazing, grounds, parking, quiet, romantic, everything. The restaurant was amazing wine cellar. The food a little exotic so if you want more basic - then head over to Cortona with a car 15 min drive up the hill. Best part of trip was having a car. The people amazing, Daniel, Enrico, and cant remember everyone - everyone was amazing."

A verified traveler stayed at Villa di Piazzano - Small Luxury Hotel of the World

Podere Spedalone

4 out of 5

Posted 8 days ago

Travelocity Verified Review

"The shower drain was not adequate and bath room as well as into bedroom pooled with water. Had to use shower with very low flow. No coffee machine in the room, one machine in breakfast room which staff only operated starting at 8;00am. Definitely a minus as wanted coffee earlier, and like to still be in pajamas in room. Pillows were flat and not supportive of neck or head. One mile of very bumpy road leading to property. Lots of flies around due to chickens and sheep on property. Room would be quite warm in summer"

A verified traveler stayed at Podere Spedalone

Tenuta Santo Pietro

5 out of 5

Posted 9 days ago

Travelocity Verified Review

"Tenuta Santo Pietro is truly a hidden gem, but what makes it so special is Bertina. She is, without a doubt, one of the most wonderful people I have ever encountered in all my years of traveling. Her warmth, kindness, attentiveness, and genuine love for what she does made our entire stay unforgettable. She goes above and beyond in every way and makes you feel so welcomed and cared for. I honestly cannot say enough wonderful things about her! The property is beautiful, the rooms are spacious, and the beds are incredibly comfortable. The restaurant is also absolutely incredible. After 10 days traveling throughout Italy, some of our favorite meals of the entire trip were here. From the exceptional wine to the pasta, desserts, and everything in between, every meal felt special. Tenuta Santo Pietro is a magical place, and Bertina is the heart of it. She made our stay truly unforgettable, and I cannot wait to return. I only hope she will be there to welcome us again. I have stayed in many wonderful places, but it is rare to meet someone who leaves such a lasting impression. Bertina is an absolute gem, and this property is so lucky to have her!"

A verified traveler stayed at Tenuta Santo Pietro