Explore top 2026 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
$451 nightly
The price is $503 total per night from Aug 1 to Aug 2
$503 total
Aug 1 - Aug 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. ...
Villa di Piazzano - Small Luxury Hotel of the World
Localita Piazzano, C.P. 6 Cortona AR
$632 nightly
The price is $704 total per night from Jul 14 to Jul 15
$704 total
Jul 14 - Jul 15
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! (240 reviews)
"10/10"
Reviewed on Jul 7, 2026
Castiglion del Bosco, A Rosewood Hotel
Localita Castiglion del Bosco Montalcino SI
Fully refundableReserve now, pay when you stay
$1,751 nightly
The price is $1,938 total per night from Aug 2 to Aug 3
$1,938 total
Aug 2 - Aug 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, ...
Castello di Velona Resort Thermal SPA & Winery
Località Velona Montalcino SI
Fully refundableReserve now, pay when you stay
$662 nightly
The price is $739 total per night from Jul 30 to Jul 31
$739 total
Jul 30 - Jul 31
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! (359 reviews)
"Is ok"
Reviewed on Jun 30, 2026
Fonteverde Thermal Spa Resort Tuscany
Localita Terme, 1 San Casciano dei Bagni SI
Fully refundableReserve now, pay when you stay
$369 nightly
The price is $411 total per night from Jul 20 to Jul 21
$411 total
Jul 20 - Jul 21
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! (205 reviews)
"One of the best places I ever was."
Reviewed on Jun 28, 2026
Monastero di Cortona Hotel & Spa
Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
$290 nightly
The price is $328 total per night from Aug 9 to Aug 10
$328 total
Aug 9 - Aug 10
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! (293 reviews)
"There are really no words for how amazing this resort truly is. From the second we walked through the doors, it exceeded five-star service. From the staff, to the room, to the resort amenities, to the restaurants, they don’t miss a single detail. Our stay has been so amazing that we extended our ..."
Reviewed on Jul 12, 2026
Il Falconiere - Relais e Chateaux
Localita San Martino 370 Cortona AR
$397 nightly
The price is $446 total per night from Jul 31 to Aug 1
$446 total
Jul 31 - Aug 1
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, ...
9.4/10 Exceptional! (133 reviews)
"Ok"
Reviewed on Jul 8, 2026
Borgo Sant'Ambrogio Resort
Loc. Sant'Ambrogio, 29 Trequanda SI
$219 nightly
The price is $244 total per night from Jul 16 to Jul 17
$244 total
Jul 16 - Jul 17
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! (119 reviews)
"My family of 4 absolutely loved this resort. Stunningly beautiful views of Pienza and the Tuscan hill country. Quiet. Relaxed. Luxurious Italian farmland. Loved it and want to return. Was the only place in Italy my family was very sad to leave. The restaurant was great. Breakfast included was very ..."
Reviewed on Jul 2, 2026
Hotel Certosa Di Maggiano
Strada di Certosa, 82/86 Siena SI
$440 nightly
The price is $496 total per night from Jul 16 to Jul 17
$496 total
Jul 16 - Jul 17
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 ...
10/10 Exceptional! (206 reviews)
"Beautiful hotel. Very supportive and friendly staff. Easy access to Siena."
Reviewed on Jul 1, 2026
Castello Banfi - Il Borgo - Relais et Chateaux
Castello di Poggio alle Mura s.n.c. Montalcino SI
$892 nightly
The price is $993 total per night from Aug 6 to Aug 7
$993 total
Aug 6 - Aug 7
Total with taxes and fees
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. ...
10/10 Exceptional! (130 reviews)
"Amazing. Everything was exceptional."
Reviewed on May 14, 2026
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
Villa di Piazzano - Small Luxury Hotel of the World
5 out of 5
Posted 5 days ago
Travelocity Verified Review
"10/10"
A verified traveler stayed at Villa di Piazzano - Small Luxury Hotel of the World
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