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.
c-hotels Club
Grand Hotel Cavour
The Moon Boutique Hotel & Spa
Hotel Berchielli
Villa Tolomei Hotel & Resort

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

Ready to book your vacation to Cortona?

 

Choose your dates

Cortona Hotel Deals

Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

5 out of 5
Localita Piazzano, C.P. 6 Cortona AR
The price is CA $929 per night from Apr 9 to Apr 10
CA $929
CA $1,035 total
Apr 9 - Apr 10
includes taxes & fees
9.8/10 Exceptional! (228 reviews)
Room was wonderful, bathroom spacious and well appointed. Staff amazing and so friendly

Reviewed on Nov 6, 2025

Villa di Piazzano - Small Luxury Hotel of the World
Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
The price is CA $386 per night from Mar 15 to Mar 16
CA $386
CA $431 total
Mar 15 - Mar 16
includes taxes & fees
Monastero di Cortona Hotel & Spa
Hotel San Michele

Hotel San Michele

4 out of 5
Via Guelfa 15 Cortona AR
The price is CA $172 per night from Mar 27 to Mar 28
CA $172
CA $195 total
Mar 27 - Mar 28
includes taxes & fees
Hotel San Michele
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

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.