Cortona Vacations

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Find the Best Cortona Vacation Packages

Cortona Hotel Deals

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Via del Salvatore Cortona AR
The price is AED 1,114 per night from Jan 4 to Jan 5
AED 1,114
AED 1,243 total
4 Jan - 5 January 2026
includes taxes & fees
9.8/10 Exceptional! (255 reviews)
Everything was perfect! Would like to give this Property a 6 Star rating. The staff made you feel like royalty!!

Reviewed on 18 December 2025

Monastero di Cortona Hotel & Spa
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
9.8/10 Exceptional! (228 reviews)
Room was wonderful, bathroom spacious and well appointed. Staff amazing and so friendly

Reviewed on 6 November 2025

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Villa di Piazzano - Small Luxury Hotel of the World
Il Falconiere - Relais e Chateaux

Il Falconiere - Relais e Chateaux

5 out of 5
Localita San Martino 370 Cortona AR
9.2/10 Wonderful! (122 reviews)
Excellent staff and experiences! We had a wonderful time.

Reviewed on 29 November 2025

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Il Falconiere - Relais e Chateaux
See all 1,192 properties in Cortona
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.

Discover the most popular places to visit in Cortona

Cortona featuring heritage architecture

Piazza della Repubblica

5/5(4 reviews)

Find out about the history of Cortona with a stop at Piazza della Repubblica. Make time to visit the cathedral and monuments while you're in the area.

Piazza della Repubblica

Villa Bramasole

You can learn about the history of Cortona with a trip to Villa Bramasole. You can enjoy the wineries while in the area.

Villa Bramasole

Cortona Cathedral

Cortona Cathedral is just one of the places to see in Cortona, so why not enjoy the other things to explore during your travels? Experience the area's museums and musical theater.

Cortona Cathedral

Frequently asked questions

How do I find cheap flights to Cortona that have flexible change policies?
When it comes to flying these days, flexibility is essential. That's why we have a "No change fee" filter to help you find cheap, flexible airfares to Cortona. It's at the top left of your screen under the "Flexible change policies" subheading.
Which airlines fly to Cortona?
Pack your bags and choose from these popular airlines that fly into or near Cortona:

  • ITA Airways - 234 flights to or near Cortona each month, including 234 flights to Fiumicino - Leonardo da Vinci Intl. Airport (FCO) per month.
  • United Airlines - 178 flights to or near Cortona each month, including 178 flights to Fiumicino - Leonardo da Vinci Intl. Airport (FCO) per month.
  • American Airlines - 164 flights to or near Cortona each month, including 164 flights to Fiumicino - Leonardo da Vinci Intl. Airport (FCO) per month.

How can I find cheap tickets to Cortona?
A great strategy for walking away with cheap airfares is to be flexible with your travel dates. Start by searching for your flight to Cortona, then click on the "flexible dates" box to see prices for nearby days. Want another tip? Book in advance. To give you an idea of costs, was the best price for a flight to Cortona in the last seven days.
How much is a flight to Cortona?
You could have locked in a round-trip flight to Cortona from anywhere between and in the last seven days. For one-way trips departing from (), the lowest amount paid during this time was .
What are the most popular airports to fly into in Cortona?
Cortona's principal airport is Fiumicino - Leonardo da Vinci Intl. Airport (FCO). Get your next awesome adventure underway by locking in an airfare on one of the 698 flights per month to this destination.
When is the cheapest time to fly to Cortona?
Leave for Cortona earlier in the week and you'll usually be rewarded with lower fares. Tuesday is typically the cheapest day to hop on a plane, followed by Monday. If you'd like to avoid the priciest flights, stay away from Saturdays.
How much is a plane ticket to Cortona?
In the last seven days, fares to Cortona varied between and . The early bird catches the worm, so find a good deal today.
What months are the cheapest to book a flight to Cortona?
February is the perfect month to get your hands on bargain flights to Cortona. Bear in mind that the most expensive time to reserve a seat in the USA isn't the middle of summer, but the month of December.
How long is a flight to Cortona?
The time your flight takes will mainly depend on the city you're traveling from. This list of the most popular routes to Cortona will give you a better idea of what to expect:

  • New York, NY (JFK-John F. Kennedy Intl.) to Fiumicino - Leonardo da Vinci Intl. Airport (FCO) - 8 hours and 30 minutes
  • Chicago, IL (ORD-O'Hare Intl.) to Fiumicino - Leonardo da Vinci Intl. Airport (FCO) - 9 hours and 12 minutes
  • Washington, DC (IAD-Washington Dulles Intl.) to Fiumicino - Leonardo da Vinci Intl. Airport (FCO) - 8 hours and 43 minutes