Explore top 2026 5 Star Hotels in Pienza
Seize Your Someday with our amazing deals for the whole family!
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Check prices for these dates
Top Pienza 5 Star hotels
Villa di Piazzano - Small Luxury Hotel of the World
Localita Piazzano, C.P. 6 Cortona AR
$639 nightly
The price is $712 total per night from Apr 14 to Apr 15
$712 total
Apr 14 - Apr 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! (229 reviews)
We really enjoyed the hotel, very clean, good atmosphere!!!
Reviewed on Apr 10, 2026
Fonteverde Lifestyle & Thermal Retreat
Localita Terme, 1 San Casciano dei Bagni SI
Fully refundableReserve now, pay when you stay
$343 nightly
The price is $382 total per night from Apr 16 to Apr 17
$382 total
Apr 16 - Apr 17
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! (191 reviews)
Great place! Excellent service by everyone we encountered.
Reviewed on Feb 13, 2026
Hotel Certosa Di Maggiano
Strada di Certosa, 82/86 Siena SI
$491 nightly
The price is $552 total per night from Apr 17 to Apr 18
$552 total
Apr 17 - Apr 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 ...
9.8/10 Exceptional! (195 reviews)
Beautiful hotel, excellent and friendly staff. Would Highly recommend, absolutely will be back.
Reviewed on Apr 12, 2026
Monastero di Cortona Hotel & Spa
Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
$305 nightly
The price is $345 total per night from Apr 19 to Apr 20
$345 total
Apr 19 - Apr 20
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! (262 reviews)
I did not drive to or from the hotel.
Reviewed on Apr 8, 2026
Precise Tale Poggio Alla Sala
Via Poggio alla Sala 10 Montepulciano SI
Fully refundableReserve now, pay when you stay
$330 nightly
The price is $370 total per night from Apr 19 to Apr 20
$370 total
Apr 19 - Apr 20
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! (126 reviews)
Most gorgeous setting, lovely staff and delicious food. We will definitely be back!
Reviewed on Apr 5, 2026
Castiglion del Bosco, A Rosewood Hotel
Localita Castiglion del Bosco Montalcino SI
Fully refundableReserve now, pay when you stay
$1,434 nightly
The price is $1,589 total per night from Apr 19 to Apr 20
$1,589 total
Apr 19 - Apr 20
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! (75 reviews)
If you don’t like th it s place, then there will never be a place on earth that you like.. it’s actually above a 5 star!! Over the top service.. food seasons breakfast fantastic…fell very lucky to have stayed here.. thank you
Reviewed on Apr 8, 2026
Borgo Sant'Ambrogio Resort
Loc. Sant'Ambrogio, 29 Trequanda SI
$147 nightly
The price is $166 total per night from Apr 14 to Apr 15
$166 total
Apr 14 - Apr 15
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 ...
9.8/10 Exceptional! (103 reviews)
Breakfast menu is basic and poor.
Reviewed on Apr 4, 2026
Castello di Velona Resort Thermal SPA & Winery
Località Velona Montalcino SI
Fully refundableReserve now, pay when you stay
$582 nightly
The price is $652 total per night from Apr 21 to Apr 22
$652 total
Apr 21 - Apr 22
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! (341 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
Il Falconiere - Relais e Chateaux
Localita San Martino 370 Cortona AR
$475 nightly
The price is $532 total per night from May 10 to May 11
$532 total
May 10 - May 11
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! (123 reviews)
Excellent staff and experiences! We had a wonderful time.
Reviewed on Nov 29, 2025
ADLER Spa Resort Thermae
Strada di Bagno Vignoni 1 San Quirico d'Orcia SI
$853 nightly
The price is $944 total per night from Apr 29 to Apr 30
$944 total
Apr 29 - Apr 30
Total with taxes and fees
This smoke-free hotel features an attached winery, a full-service spa, and hot springs. There's fun for all ages with a free kid's club and a playground, and ...
9.4/10 Exceptional! (69 reviews)
Everything was close to perfect
Reviewed on Mar 27, 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 3 days ago
Travelocity Verified Review
"We really enjoyed the hotel, very clean, good atmosphere!!! "
A verified traveler stayed at Villa di Piazzano - Small Luxury Hotel of the World
Explore More Ways to Travel with Travelocity
- Apartments in San Quirico d'Orcia
- Winery Hotels in San Quirico d'Orcia
- San Quirico d'Orcia Hotels
- San Giovanni d'Asso Hotels
- Villas in San Giovanni d'Asso
- Spa Resorts & in Bagno Vignoni
- Bagno Vignoni Hotels
- 3 Star Hotels in Arezzo
- 4 Star Hotels in Arezzo
- Cervognano Montenero Hotels
- Inns in Amorosa
- 5 Star Hotels in La Cava
- 5 Star Hotels in Brunello di Montalcino Wine Area
- Farmstay in Montalcino
- Apartments in Montalcino
- B&B in Montalcino
- Kid Friendly Hotels in Montalcino
- Hotels with Suites in Montalcino
- Luxury Hotels in Montalcino
- Winery Hotels in Montalcino
- Montalcino Hotels
- Villas in Montalcino
- Holiday Park Resorts in Torrita di Siena
- Cheap Hotels in Torrita di Siena
- Farmstay in Chianciano Terme
- B&B in Chianciano Terme
- Historic Hotels in Chianciano Terme
- Oceanfront Hotels in Chianciano Terme
- Spa Resorts & in Chianciano Terme
- Chianciano Terme Hotels
- 5 Star Hotels in Cortona
- Vacation Homes in Rocca d'Orcia
- Resorts in Rocca d'Orcia
- 3 Star Hotels in Montepulciano
- Farmstay in Montepulciano
- B&B in Montepulciano
- Adults Only Resorts & in Montepulciano
- All Inclusive Resorts & in Montepulciano
- Hotels with Pools in Montepulciano
- Hotels with Balconies in Montepulciano
- Hotels with Free Breakfast in Montepulciano
- Hotels with Free Airport Shuttle in Montepulciano
- Hotels with Hot Tubs in Montepulciano
- Pet Friendly Hotels in Montepulciano
- Spa Resorts & in Montepulciano
- Hotel Wedding Venues Hotels in Montepulciano
- Winery Hotels in Montepulciano
- Montepulciano Hotels
- Inns in Montepulciano
- Pousadas in Montepulciano
- Vacation Homes in Montepulciano
- Resorts in Montepulciano
- Town Houses in Montepulciano
- Villas in Montepulciano
- Extended Stay Hotels in Val d'Orcia
- Adults Only Resorts & in Val d'Orcia
- Golf Resorts & in Val d'Orcia
- Hotels with a Gym in Val d'Orcia
- Val d'Orcia Hotels
- Lodges in Val d'Orcia
- Villas in Val d'Orcia
- 4 Star Hotels in Siena
- 5 Star Hotels in Siena
- Boutique Hotels in Acquaviva
- Farmstay in Castiglione d'Orcia
- Castiglione d'Orcia Hotels
- Montisi Hotels
- Trequanda Hotels
- Osteria delle Noci Hotels