Explore top 2025 5 Star Hotels in Pienza

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Top Pienza 5 Star hotels

Fonteverde Lifestyle & Thermal Retreat

Fonteverde Lifestyle & Thermal Retreat

5 out of 5
Localita Terme, 1 San Casciano dei Bagni SI
Fully refundableReserve now, pay when you stay
$323 nightly
The price is $360 total per night from Dec 10 to Dec 11
$360 total
Dec 10 - Dec 11
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 ...
9.2/10 Wonderful! (179 reviews)
Best resort I’ve ever stayed in! So clean, bathroom is refreshing, the many thermal pools, the views, I’ll be going back every year.

Reviewed on Oct 25, 2025

Opens in a new windowFonteverde Lifestyle & Thermal Retreat
Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
$294 nightly
The price is $332 total per night from Dec 21 to Dec 22
$332 total
Dec 21 - Dec 22
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 ...
9.8/10 Exceptional! (251 reviews)
What a unique place. Near the top of the hill. Staff service and amenities were all great. Not an easy place to drive to. The taxis drive-in backwards the last eighth of a mile.

Reviewed on Nov 4, 2025

Opens in a new windowMonastero di Cortona Hotel & Spa
Rosewood Castiglion del Bosco

Rosewood Castiglion del Bosco

5 out of 5
Localita Castiglion del Bosco Montalcino SI
Fully refundableReserve now, pay when you stay
$1,297 nightly
The price is $1,439 total per night from Dec 21 to Dec 22
$1,439 total
Dec 21 - Dec 22
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, ...
10/10 Exceptional! (68 reviews)
Beautiful property and great service. Was a little disappointed they charge double the price for wine they make in their back yard then I pay here in Montreal.

Reviewed on Aug 3, 2025

Opens in a new windowRosewood Castiglion del Bosco
Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

5 out of 5
Località Velona Montalcino SI
Fully refundableReserve now, pay when you stay
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 ...
8.8/10 Excellent! (337 reviews)
The property was exquisite. The view spectacular and the staff top notch. The indoor and outdoor thermal pools and sauna made our stay very relaxing. The buffet breakfast was amazing.

Reviewed on Nov 11, 2025

Opens in a new windowCastello di Velona Resort Thermal SPA & Winery
Borgo Sant'Ambrogio Resort

Borgo Sant'Ambrogio Resort

5 out of 5
Loc. Sant'Ambrogio, 29 Trequanda SI
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $126 total per night from Nov 30 to Dec 1
$126 total
Nov 30 - Dec 1
Total with taxes and fees
This farm stay features a restaurant, a seasonal outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public ...
9.6/10 Exceptional! (94 reviews)
I had an amazing stay at Borgo Sant’Ambrogio Resort. The property is absolutely beautiful with breathtaking views of the Tuscan landscape. It exceeded my expectations in every way. The staff was warm and friendly which made the experience even more special. I would highly recommend this resort to ...

Reviewed on Sep 17, 2025

Opens in a new windowBorgo Sant'Ambrogio Resort
Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

5 out of 5
Localita Piazzano, C.P. 6 Cortona AR
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! (228 reviews)
Room was wonderful, bathroom spacious and well appointed. Staff amazing and so friendly

Reviewed on Nov 6, 2025

Opens in a new windowVilla di Piazzano - Small Luxury Hotel of the World
Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Via 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. ...
9.4/10 Exceptional! (123 reviews)
Perfect escape
Fantastic hotel in an incredible setting. Staff were extremely helpful, attentive and understanding. The perfect location for a relaxing break and a centre for exploring Tuscany

Reviewed on Oct 27, 2025

Opens in a new windowPrecise Tale Poggio Alla Sala
Mercure Petriolo Siena Terme Spa Hotel

Mercure Petriolo Siena Terme Spa Hotel

5 out of 5
Strada Provinciale di Petriolo Civitella Paganico GR
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $115 total per night from Dec 11 to Dec 12
$115 total
Dec 11 - Dec 12
Total with taxes and fees
This luxury hotel's full-service spa and hot springs are among the highlights. Enjoy the indoor pool and perks like free self parking. You'll appreciate the ...
8.6/10 Excellent! (229 reviews)
We had a great time. I would recommend this hotel when in Tuscany.

Reviewed on Oct 11, 2025

Opens in a new windowMercure Petriolo Siena Terme Spa Hotel
Castello Banfi - Il Borgo - Relais et Chateaux

Castello Banfi - Il Borgo - Relais et Chateaux

5 out of 5
Castello di Poggio alle Mura s.n.c. Montalcino SI
An attached winery, 2 restaurants, and a gym are all featured at this smoke-free hotel. Families will appreciate complimentary bicycles and in-room childcare. ...
9.8/10 Exceptional! (125 reviews)
Everything about this property is exquisite. Spacious room w/ Tuscan countryside views, unbelievable soft linens, amazing breakfast. The service is also what you would expect from a 5 star property. One of the best places we have stayed in the world. We will always come back when considering coming ...

Reviewed on Nov 4, 2025

Opens in a new windowCastello Banfi - Il Borgo - Relais et Chateaux
Castel Monastero - The Leading Hotels of the World

Castel Monastero - The Leading Hotels of the World

5 out of 5
Monastero D'Ombrone Castelnuovo Berardenga SI
Fully refundableReserve now, pay when you stay
$560 nightly
The price is $627 total per night from Dec 2 to Dec 3
$627 total
Dec 2 - Dec 3
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 ...
8.8/10 Excellent! (144 reviews)
Overall great. It was a bit colder when we went. I wish they put heat lamps in outside seating areas in the evenings. I did ask and they put one but it needed time to heat up. But other than that - amazing stay!

Reviewed on Oct 4, 2025

Opens in a new windowCastel Monastero - The Leading Hotels of the World
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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.

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