Explore top 2025 5 Star Hotels in Pienza

Name: Castel Monastero - The Leading Hotels of the World
Price range: $627 total
Rating: 8.8

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Top Pienza 5 Star hotels

Fonteverde Lifestyle & Thermal Retreat

Localita Terme, 1 San Casciano dei Bagni SI

Fully refundableReserve now, pay when you stay

$323 nightly

$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

Monastero di Cortona Hotel & Spa

Via del Salvatore Cortona AR

Fully refundableReserve now, pay when you stay

$294 nightly

$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

Rosewood Castiglion del Bosco

Localita Castiglion del Bosco Montalcino SI

Fully refundableReserve now, pay when you stay

$1,297 nightly

$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

Castello di Velona Resort Thermal SPA & Winery

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

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Borgo Sant'Ambrogio Resort

Loc. Sant'Ambrogio, 29 Trequanda SI

Fully refundableReserve now, pay when you stay

$111 nightly

$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

Villa di Piazzano - Small Luxury Hotel of the World

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

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Precise Tale Poggio Alla Sala

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

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Mercure Petriolo Siena Terme Spa Hotel

Strada Provinciale di Petriolo Civitella Paganico GR

Fully refundableReserve now, pay when you stay

$104 nightly

$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

Castello Banfi - Il Borgo - Relais et Chateaux

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

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Castel Monastero - The Leading Hotels of the World

Monastero D'Ombrone Castelnuovo Berardenga SI

Fully refundableReserve now, pay when you stay

$560 nightly

$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

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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.