Search for Cheap Deals on
5 Star Hotels in Pienza

You choose what matters — star rating, location, amenities.

We pick the perfect hotel, packed with all your must-haves.

Your hotel is revealed right after booking!


Featured 5 Star Pienza Hotels

Villa di Piazzano - Small Luxury Hotel of the World
5 out of 5
Fully refundableReserve now, pay when you stay
  • 50 min drive from Pienza Cathedral
The price is $604 per night from Apr 16 to Apr 17
$604
includes taxes & fees
Apr 16 - Apr 17
Stay at this 5-star luxury hotel in Cortona. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...
Villa di Piazzano - Small Luxury Hotel of the World
Precise Tale Poggio Alla Sala
5 out of 5
Fully refundableReserve now, pay when you stay
  • 20 min drive from Pienza Cathedral
The price is $446 per night from Apr 17 to Apr 18
$446
includes taxes & fees
Apr 17 - Apr 18
Stay at this 5-star luxury hotel in Montepulciano. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
Precise Tale Poggio Alla Sala
Borgo Sant'Ambrogio Resort
5 out of 5
  • 7 min drive from Pienza Cathedral
The price is $134 per night from Apr 16 to Apr 17
$134
includes taxes & fees
Apr 16 - Apr 17
Stay at this 5-star luxury farm stay in Trequanda. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...
Borgo Sant'Ambrogio Resort
Save an average of 15% on thousands of hotels when you're signed in
Il Falconiere - Relais e Chateaux
5 out of 5
Fully refundableReserve now, pay when you stay
  • 49 min drive from Pienza Cathedral
The price is $453 per night from Apr 22 to Apr 23
$453
includes taxes & fees
Apr 22 - Apr 23
Stay at this 5-star luxury hotel in Cortona. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Cortona Cathedral and Museo Diocesano are ...
Il Falconiere - Relais e Chateaux
Rosewood Castiglion del Bosco
5 out of 5
Fully refundableReserve now, pay when you stay
  • 27 min drive from Pienza Cathedral
The price is $1,369 per night from Apr 18 to Apr 19
$1,369
includes taxes & fees
Apr 18 - Apr 19
Stay at this 5-star luxury hotel in Montalcino. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Castiglion del Bosco Winery and Corte ...
Rosewood Castiglion del Bosco
Monastero di Cortona Hotel & Spa
5 out of 5
Fully refundableReserve now, pay when you stay
  • 49 min drive from Pienza Cathedral
The price is $448 per night from Apr 30 to May 1
$448
includes taxes & fees
Apr 30 - May 1
Stay at this 5-star luxury hotel in Cortona. Enjoy free breakfast, free WiFi, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
Monastero di Cortona Hotel & Spa
Fonteverde Lifestyle & Thermal Retreat
5 out of 5
Fully refundableReserve now, pay when you stay
  • 40 min drive from Pienza Cathedral
The price is $417 per night from May 13 to May 14
$417
includes taxes & fees
May 13 - May 14
Stay at this 5-star luxury hotel in San Casciano dei Bagni. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Fonteverde Terme and Pasticceria ...
Fonteverde Lifestyle & Thermal Retreat
Castello di Velona Resort Thermal SPA & Winery
5 out of 5
Fully refundableReserve now, pay when you stay
  • 21 min drive from Pienza Cathedral
The price is $534 per night from Apr 17 to Apr 18
$534
includes taxes & fees
Apr 17 - Apr 18
Stay at this 5-star luxury hotel in Montalcino. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Abbazia di Sant'Antimo and Museum of Brunello ...
Castello di Velona Resort Thermal SPA & Winery
Castello Banfi - Il Borgo
5 out of 5
  • 31 min drive from Pienza Cathedral
The price is $988 per night from Apr 16 to Apr 17
$988
includes taxes & fees
Apr 16 - Apr 17
Stay at this 5-star luxury hotel in Montalcino. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Castello Banfi and Poggio Antico are ...
Castello Banfi - Il Borgo
 La Bagnaia Golf Resort
5 out of 5
Fully refundableReserve now, pay when you stay
  • 49 min drive from Pienza Cathedral
The price is $254 per night from Apr 30 to May 1
$254
includes taxes & fees
Apr 30 - May 1
Stay at this 5-star luxury hotel in Murlo. Enjoy free WiFi, free parking, and an outdoor pool. Popular attraction Val di Merse is located nearby.
La Bagnaia Golf Resort
Castel Monastero - The Leading Hotels of the World
5 out of 5
Fully refundableReserve now, pay when you stay
  • 48 min drive from Pienza Cathedral
The price is $647 per night from Apr 16 to Apr 17
$647
includes taxes & fees
Apr 16 - Apr 17
Stay at this 5-star luxury hotel in Castelnuovo Berardenga. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Villa a Sesta Polo Club and ...
Castel Monastero - The Leading Hotels of the World
ADLER Spa Resort Thermae
5 out of 5
  • 10 min drive from Pienza Cathedral
The price is $849 per night from Apr 16 to Apr 17
$849
includes taxes & fees
Apr 16 - Apr 17
Stay at this 5-star luxury hotel in San Quirico d'Orcia. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Piazza delle Sorgenti and Tenuta ...
ADLER Spa Resort Thermae
Don't see what you're looking for?
See all available properties in Pienza
View all properties
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.

5-Star Hotel in Pienza

It’s time. No more meh motels and so-so stays. This vacation it’s all about living it up, and that starts with a great hotel. You want first-class service and award-winning restaurants. Well, let us introduce you to a 5-star hotel in Pienza.

So nice you’ll blink twice

What makes a hotel worthy of supreme star-age? For starters, the service has to be top-notch and personalized. These hotels often have 24-hour room service, a welcome gift upon your arrival, and help you with your bags—even if you travel light.

Are they nicer? Heck yeah, they are! Most 5-star hotels have jaw-dropping aesthetics that give an authentic feel of class. And we’re not talking about that faux-gold soap dish your Aunt Tilda puts out for the guests—it’s the real deal.

Stars in your eyes

Are 5-stars hotels worth it? If you like the finer things in life, then yes, they sure are. But we also know you’re the type that likes to get your caviar on a fish stick budget. We’re right there with you, and that is why we make it easy to find the best 5-star hotel in Pienza for you. Sort by:

  • Price: Want to live large, but keep that budget balanced? We got you. We have 5-star hotels starting at $134.

  • Amenities: Pienza skyline view? Maybe a heated indoor pool? Looking for a Michelin-star restaurant? Search for the hotels that have the amenities you desire.

  • Hotwire Hot Rate: We’ll tell you the name of the hotel after you book, and you might just save a ton.

When you’re looking for the top 5-star hotels in Pienza—but don’t want to pay top dollar—let us help you out. You can get that posh palace of your dreams, and have money left to take on Pienza your way.