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5 Star Hotels in Pienza

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Featured 5 Star Pienza Hotels

Villa di Piazzano - Small Luxury Hotel of the World
5 out of 5
  • 50 min drive from Pienza Cathedral
The price is $611 per night from Oct 7 to Oct 8
$611
includes taxes & fees
Oct 7 - Oct 8
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 $559 per night from Oct 8 to Oct 9
$559
includes taxes & fees
Oct 8 - Oct 9
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
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 $321 per night from Oct 7 to Oct 8
$321
includes taxes & fees
Oct 7 - Oct 8
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
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Fonteverde Lifestyle & Thermal Retreat
5 out of 5
Fully refundableReserve now, pay when you stay
  • 40 min drive from Pienza Cathedral
The price is $447 per night from Sep 26 to Sep 27
$447
includes taxes & fees
Sep 26 - Sep 27
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
Castel Monastero
5 out of 5
Fully refundableReserve now, pay when you stay
  • 48 min drive from Pienza Cathedral
The price is $547 per night from Oct 3 to Oct 4
$547
includes taxes & fees
Oct 3 - Oct 4
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
Rosewood Castiglion del Bosco
5 out of 5
  • 27 min drive from Pienza Cathedral
The price is $1,782 per night from Oct 16 to Oct 17
$1,782
includes taxes & fees
Oct 16 - Oct 17
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
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 $966 per night from Oct 5 to Oct 6
$966
includes taxes & fees
Oct 5 - Oct 6
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
Relais Il Falconiere
5 out of 5
Fully refundableReserve now, pay when you stay
  • 49 min drive from Pienza Cathedral
The price is $527 per night from Sep 23 to Sep 24
$527
includes taxes & fees
Sep 23 - Sep 24
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 ...
Relais Il Falconiere
 La Bagnaia Golf Resort
5 out of 5
Fully refundableReserve now, pay when you stay
  • 49 min drive from Pienza Cathedral
The price is $221 per night from Oct 15 to Oct 16
$221
includes taxes & fees
Oct 15 - Oct 16
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
ADLER Spa Resort Thermae
5 out of 5
  • 10 min drive from Pienza Cathedral
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
Borgo Sant'Ambrogio Resort
5 out of 5
  • 7 min drive from Pienza Cathedral
The price is $227 per night from Oct 10 to Oct 11
$227
includes taxes & fees
Oct 10 - Oct 11
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
Castello Banfi - Il Borgo
5 out of 5
  • 31 min drive from Pienza Cathedral
The price is $1,539 per night from Sep 18 to Sep 19
$1,539
includes taxes & fees
Sep 18 - Sep 19
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
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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 $221.

  • 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.