Guazzino
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Villa di Piazzano - Small Luxury Hotel of the World
Localita Piazzano, C.P. 6 Cortona AR
The price is CA $832 per night from Sep 2 to Sep 3
CA $832
CA $928 total
Sep 2 - Sep 3
includes taxes & fees
Book a stay at this luxury hotel in Cortona. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...
9.8/10 Exceptional! (246 reviews)
"It was a spectacular stay and so peaceful! All the staff were super helpful and the quality of service, amenities, and food really shined. Before we actually arrived, the staff would check in with us leading up to make sure we were all set up and all our requests answered. They also helped us prepare ..."
Reviewed on Sep 1, 2026
Precise Tale Poggio Alla Sala
Via Poggio alla Sala 10 Montepulciano SI
Fully refundableReserve now, pay when you stay
The price is CA $714 per night from Sep 28 to Sep 29
CA $714
CA $795 total
Sep 28 - Sep 29
includes taxes & fees
Book a stay at this luxury hotel in Montepulciano. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
9.6/10 Exceptional! (165 reviews)
"Fantastic stay!"
Reviewed on Aug 30, 2026
Monastero di Cortona Hotel & Spa
Via del Salvatore Cortona AR
The price is CA $499 per night from Sep 2 to Sep 3
CA $499
CA $562 total
Sep 2 - Sep 3
includes taxes & fees
Book a stay at this luxury hotel in Cortona. Enjoy free breakfast, free WiFi, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
10/10 Exceptional! (320 reviews)
"Amazing beautiful hotel in such a lovely town. Easy to travel to other small towns as well. The staff was very accommodating. The breakfast was great. Such a beautiful resort that was an old monastery on top of the hill. One tip would be to pay for a parking spot in the hotel. Otherwise you will ..."
Reviewed on Sep 1, 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.
Hotel San Gregorio
Via Della Madonnina 4 Pienza SI
Book a stay at this business-friendly residence in Pienza. Enjoy free WiFi, an outdoor pool, and room service. Popular attractions Enoteca Di Ghino and Artemisia ...
Casanova - Panoramic Rooms and Suites
Strada Provinciale 146 di Chianciano San Quirico d'Orcia SI
Stay at this residence in San Quirico d'Orcia. Enjoy free breakfast, free WiFi, and an outdoor pool. Popular attractions Horti Leonini and Chapel of our Lady ...
9.2/10 Wonderful! (93 reviews)
"Our stay at Casanova Panoramic Rooms was absolutely wonderful. The room was beautiful, spotless, and the view was simply breathtaking. The entire check-in process was smooth and welcoming, and having convenient parking made everything even easier. We also loved the restaurant—the food was delicious, ..."
Reviewed on Jul 7, 2026
Residenza Fabroni
Via di Gracciano nel Corso, 12 Montepulciano SI
Book a stay at this historic residence in Montepulciano. Enjoy free WiFi, an attached winery, and a rooftop terrace. Popular attractions Torre di Pulcinella ...
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.
Things to do
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
CA $136
per adult
98% of travellers recommend
Oil museum and oil mill in Tuscany: tour and tasting
CA $32
per adult
Tasting Tour in One of The Most Beautiful Cellars in the World
CA $53
per adult
100% of travellers recommend
Montepulciano Wine Tasting in the Tuscan Countryside
CA $40
per adult
Montepulciano: Artisan Heroic Wine Tasting at the Terrace
CA $81
per adult
