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Hotel Relais II Chiostro di Pienza
Corso Rossellino 26, Pienza, SI
$76 nightly
The price is $91 total per night from Oct 26 to Oct 27
$91 total
Oct 26 - Oct 27
Total with taxes and fees
Stay at this 4-star hotel in Pienza. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions ...
8.6/10 Excellent! (598 reviews)
"The perfect location. Gorgeous property. Excellent breakfast."
Reviewed on Oct 4, 2025

Monastero di Cortona Hotel & Spa
Via del Salvatore, Cortona, AR
$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
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 ...
9.8/10 Exceptional! (239 reviews)
"Beautiful, unique property! Stunning views of the countryside. The staff were all very helpful and friendly. We will definitely recommend!"
Reviewed on Sep 27, 2025

Hotel Panoramic
Via di Villa Bianca, 8, Montepulciano, SI
$107 nightly
The price is $122 total per night from Oct 22 to Oct 23
$122 total
Oct 22 - Oct 23
Total with taxes and fees
Stay at this 3-star family-friendly hotel in Montepulciano. Enjoy an outdoor pool, a rooftop terrace, and room service. Popular attractions Terme di Montepulciano ...
8.6/10 Excellent! (248 reviews)
"Nice location. Staff was nice. The only issue is the room with no AC or plugs. When reviewing the property it appeared the property lists AC. You would assume the whole hotel has AC. Once I selected the room I should have looked closely at the AC availability. Rough night to sleep. Other than that ..."
Reviewed on Jul 26, 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.

Hotel San Gregorio
Via Della Madonnina 4, Pienza, SI
Stay at this 3-star business-friendly residence in Pienza. Enjoy free WiFi, an outdoor pool, and room service. Popular attractions RI Crea RE and Enoteca Di ...
9.2/10 Wonderful! (129 reviews)
Pienza getaway
"I don't know where to begin the hotel is in center of everything nice underground parking garage and the staff couldn't been any friendly, helpful and caring The reception staffs their where excelent if We are coming back to pienza staying there 💯 percent thanks you so much"
Reviewed on Sep 1, 2025

Casanova - Panoramic Rooms and Suites
Strada Provinciale 146 di Chianciano, Località Casanova 6/c, San Quirico d'Orcia, SI
Stay at this 3-star residence in San Quirico d'Orcia. Enjoy free breakfast, free WiFi, and an outdoor pool. Popular attractions Horti Leonini and Chapel of our ...
9/10 Wonderful! (70 reviews)
"Delightful stay. The room was lovely, and the view from our private terrace was wonderful. Dinner was first rate. Easily walkable into San Quirico, short drive to Montalcino, Pienza, and Montalcino. Nice massage and spa. A very good value."
Reviewed on Oct 1, 2025

Abbadia Sicille Relais
SP 14 Loc. Abbadia Sicille, Trequanda, SI
Stay at this 4-star business-friendly residence in Trequanda. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Monastery of Sant'Anna ...
8.8/10 Excellent! (155 reviews)
An amazing find. Would love to return
"An amazing place with a luxury feel. Comfy, welcoming and peacefully relaxing"
Reviewed on Nov 30, 2024
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.
Popular places to visit
The Saints Peter and Andrew Church
After visiting The Saints Peter and Andrew Church, make a plan to see the other sights and activities in Trequanda. Visit the area's spas, or simply enjoy its wineries.
Things to do

Montalcino: Guided Winery Tour and Wine Tasting
$53
per adult

Montepulciano Wine Tasting in the Tuscan Countryside
$30
per adult

From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
$105
per adult
100% of travellers recommend

Seggiano: Guided Tour of the Olive Grove and Food Tasting
$30
per adult

Oil museum and oil mill in Tuscany: tour and tasting
$24
per adult

Montepulciano: Artisan Heroic Wine Tasting at the Terrace
$51
per adult
Explore a world of travel with Expedia
Explore a world of travel with Expedia
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- Visit Petroio
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- Museo del Tartufo
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- Bosco della Ragnaia
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- Pieve di Corsignano
- Enoteca Di Ghino
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- Palazzo Piccolomini
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- Pienza Cathedral
- Piazza Pio II
- Palazzo Borgia
- Chapel of our Lady of Vitaleta
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- Lake Trasimeno
- Monte Amiata
- Castello Banfi
- Valdichiana Outlet Village
- Piazza Grande
- Pienza Cathedral
- Terme di Chianciano
- San Giovanni Terme Rapolano
- Piscine Termali Theia
- Baths of San Filippo
- Terme di Montepulciano Spa
- Tenuta Greppo Franco Biondi Santi
- Terme Antica Querciolaia
- Val di Chiana
- Dome of Montepulciano
- Fortress of Montalcino
- Piazza Italia
- Crete Senesi
- Terme Petriolo
- Castiglion del Bosco Winery
- Palazzo Avignonesi
- Palazzo Ricci
- Chapel of our Lady of Vitaleta
- Monte Oliveto Maggiore Abbey
- Siena Circuit
- La Foce
- Piazza della Repubblica
- Villa a Sesta Polo Club
- Abbazia di Sant'Antimo
- Palazzo Piccolomini
- Cantina del Redi
- Cantina Contucci