
Cortona Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to CA $1,096 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
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.

Cappuccina Country Resort
per person
Aug 17 - Aug 23
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
8.4/10 Very Good! (69 reviews)
We absolutely loved our stay. I wish we got to stay longer. The hotel and the town are so lovely and peaceful. I could have easily stayed there for three days. The staff was so kind. The room was comfortable and very luxurious. Breakfast was yummy.
Reviewed on May 28, 2025




Eurostars Florence Boutique
Historic Centre of Florence
Save 100% on your flight
per person
Sep 21 - Sep 27
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
8.6/10 Excellent! (462 reviews)
Breakfast was very good and the staff were excellent. Expresso in the morning was on point.
Reviewed on Jul. 5, 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 $799 per night from Jul 21 to Jul 22
CA $799
CA $892 total
Jul 21 - Jul 22
includes taxes & fees
9.6/10 Exceptional! (211 reviews)
"Our recent 4 night stay at Villa di Piazzano was truly perfect in every way! Celebrating our 40th wedding anniversary could not have been more enjoyed! Having booked our stay 6 mos in advance - I communicated many times via email during that time, seeking itinerary advice from the Conceirge. I always ..."
Reviewed on Jun. 24, 2025

Monastero di Cortona Hotel & Spa
Via del Salvatore, Cortona, AR
Fully refundableReserve now, pay when you stay
The price is CA $450 per night from Jul 13 to Jul 14
CA $450
CA $508 total
Jul 13 - Jul 14
includes taxes & fees
9.8/10 Exceptional! (215 reviews)
"Amazing hotel, a must stay if visiting Cortona..best hotel in Tuscany"
Reviewed on Jul. 5, 2025

Il Falconiere - Relais e Chateaux
Localita San Martino 370, Cortona, AR
The price is CA $534 per night from Aug 4 to Aug 5
CA $534
CA $601 total
Aug 4 - Aug 5
includes taxes & fees
9.2/10 Wonderful! (108 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

Cortona Private walking Tour under the Tuscan sun
CA $470
per adult
Frequently asked questions
Other vacations you might like
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals
Expedia's Latest Trends
Hotels
- Winery Hotels in Montepulciano
- Hotels with Free Breakfast in Florence
- Hotels in Capri
- Hotels in Sorrento
- Hotels in Taormina
- Hotels in Siena
- Hotels in Lucca
- All Inclusive Resorts and Hotels in Florence
- Hotels in Florence
- Hotels in Positano
- Hotels in San Gimignano
- Winery Hotels in Siena
- Hotels with Free Airport Shuttle in Florence
- Hotels in Portofino
- Hotels in Pisa
Activities
Packages
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.