
Cortona Vacation Packages
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Your Cortona Vacation
With plenty of highlights as well as hidden gems, this city is best experienced with a Cortona vacation package. Find a place to stay in Contrada Castello, which is good for dining, views and culture. Ready to explore? Villa Bramasole, Piazza della Repubblica and Cathedral of Cortona are just a few of the top-rated places to visit during your trip to Cortona. Whoever you're going away with and whatever the size of your budget, your ultimate Cortona vacation is only clicks away with Expedia.
Top Cortona Vacation Deals
Price found within the past 48 hours. Click for updated prices.



Eurostars Florence Boutique
Historic Centre of Florence
per person
Oct 2 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
8.6/10 Excellent! (468 reviews)
Great little hotel. Everything is within walking distance. The view from the terrace was amazing.
Reviewed on Aug. 6, 2025

Cortona Hotel Deals

Villa di Piazzano - Small Luxury Hotel of the World
Localita Piazzano, C.P. 6, Cortona, AR
Fully refundableReserve now, pay when you stay
The price is CA $792 per night from Aug 19 to Aug 20
CA $792
CA $884 total
Aug 19 - Aug 20
includes taxes & fees
9.6/10 Exceptional! (218 reviews)
"AMAZING! Gorgeous! I would recommend to everyone!"
Reviewed on Jul. 29, 2025

Monastero di Cortona Hotel & Spa
Via del Salvatore, Cortona, AR
Fully refundableReserve now, pay when you stay
The price is CA $423 per night from Aug 24 to Aug 25
CA $423
CA $478 total
Aug 24 - Aug 25
includes taxes & fees
9.8/10 Exceptional! (228 reviews)
"Beautiful property, magical, great friendly staff, fantastic breakfast. Everything was perfect"
Reviewed on Aug. 7, 2025

Il Falconiere - Relais e Chateaux
Localita San Martino 370, Cortona, AR
The price is CA $517 per night from Sep 1 to Sep 2
CA $517
CA $581 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (111 reviews)
"Perfect stay! Couldn’t recommend more highly"
Reviewed on Jul. 8, 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.
What to do in Cortona

From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
CA $183
per adult
100% of travellers recommend

Montepulciano: Wine Tour and tasting
CA $84
per adult
100% of travellers recommend
Frequently asked questions
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.