Explore top 2025 5 Star Hotels in Pienza
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Top Pienza 5 Star hotels
Precise Tale Poggio Alla Sala
Via Poggio alla Sala 10, Montepulciano, SI
Fully refundableReserve now, pay when you stay
$414 nightly
The price is $463 total per night from Nov 1 to Nov 2
$463 total
Nov 1 - Nov 2
Total with taxes and fees
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! (115 reviews)
"Loved everything about this property! The spa is a lovely experience. Next time will stay longer"
Reviewed on Oct 8, 2025
Villa di Piazzano - Small Luxury Hotel of the World
Localita Piazzano, C.P. 6, Cortona, AR
Fully refundableReserve now, pay when you stay
$600 nightly
The price is $669 total per night from Oct 22 to Oct 23
$669 total
Oct 22 - Oct 23
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 ...
9.6/10 Exceptional! (223 reviews)
"I stayed at Villa di Piazzano for two nights and overall had a lovely experience. The check-in process was seamless, and the staff were warm, professional, and very attentive, which set a great tone from the start. The property itself is absolutely gorgeous, with beautiful grounds and a peaceful ..."
Reviewed on Sep 23, 2025
Fonteverde Lifestyle & Thermal Retreat
Localita Terme, 1, San Casciano dei Bagni, SI
Fully refundableReserve now, pay when you stay
$363 nightly
The price is $404 total per night from Nov 6 to Nov 7
$404 total
Nov 6 - Nov 7
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! (175 reviews)
"Ok"
Reviewed on Oct 5, 2025
Castello di Velona Resort Thermal SPA & Winery
Località Velona, Castelnuovo dell'Abate, 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! (331 reviews)
"Me and my wife stayed there for our honeymoon. We had an exceptional time. The service was exceptional. The pools and amenities were very nice. Great! Breakfast was just free. Located close to montel Chino and many great wineries. Specifically, we really enjoyed the wine tasting. The entire staff ..."
Reviewed on Sep 11, 2025
Monastero di Cortona Hotel & Spa
Via del Salvatore, Cortona, AR
Fully refundableReserve now, pay when you stay
$263 nightly
The price is $294 total per night from Nov 2 to Nov 3
$294 total
Nov 2 - Nov 3
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! (243 reviews)
"fabulous hotel with the most beautiful aperol spritz I have ever had served by the pool, and that was only one of the wonderful things I have to say about this beautiful hotel. The staff were helpful and accomodating, breakfast in the courtyard outstanding and our room was divine. Cant recommend ..."
Reviewed on Oct 9, 2025
Rosewood Castiglion del Bosco
Localita Castiglion del Bosco, Montalcino, SI
Fully refundableReserve now, pay when you stay
$1,285 nightly
The price is $1,426 total per night from Nov 2 to Nov 3
$1,426 total
Nov 2 - Nov 3
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! (66 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
Castel Monastero - The Leading Hotels of the World
Monastero D'Ombrone, Castelnuovo Berardenga, SI
$502 nightly
The price is $564 total per night from Nov 2 to Nov 3
$564 total
Nov 2 - Nov 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
Mercure Petriolo Siena Terme Spa Hotel
Strada Provinciale di Petriolo, Civitella Paganico, GR
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $141 total per night from Oct 27 to Oct 28
$141 total
Oct 27 - Oct 28
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! (224 reviews)
"Very nice and location is quiet. You need a car to get out and about"
Reviewed on Oct 1, 2025
Il Falconiere - Relais e Chateaux
Localita San Martino 370, Cortona, AR
$269 nightly
The price is $301 total per night from Nov 4 to Nov 5
$301 total
Nov 4 - Nov 5
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, ...
9.2/10 Wonderful! (119 reviews)
"Spectacular! From the small details to the views, restaurant, service, everything was beautiful. I would love to stay again at this place."
Reviewed on Oct 7, 2025
La Posta Hotel & Thermal Spa
Via Ara Urcea 43, Bagno Vignoni, San Quirico d'Orcia, SI
$376 nightly
The price is $420 total per night from Nov 3 to Nov 4
$420 total
Nov 3 - Nov 4
Total with taxes and fees
A full-service spa, 2 outdoor pools, and an indoor pool are all featured at this smoke-free hotel. Enjoy a meal from the restaurant and perks like free buffet ...
9.6/10 Exceptional! (68 reviews)
"This is the 4th time we stayed in this hotel . I love the fact that it’s like a retreat hotel . You are there to relax and soak yourself to the natural hot spring . The restaurant have fabulous healthy breakfast and dinner . I love Val D’Orcia . It’s a relaxing town with beautiful scenery and same ..."
Reviewed on Sep 24, 2025
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.
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
Monastero di Cortona Hotel & Spa
5 out of 5
Posted 4 days ago
Travelocity Verified Review
"fabulous hotel with the most beautiful aperol spritz I have ever had served by the pool, and that was only one of the wonderful things I have to say about this beautiful hotel. The staff were helpful and accomodating, breakfast in the courtyard outstanding and our room was divine. Cant recommend this property enough."
A verified traveler stayed at Monastero di Cortona Hotel & Spa
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