Cortona Vacations

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Cortona Hotel Deals

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 AED 1,032 per night from Nov 20 to Nov 21
AED 1,032
AED 1,152 total
20 Nov - 21 Nov
includes taxes & fees
9.8/10 Exceptional! (249 reviews)
Incredible hotel with amazing staff

Reviewed on 1 November 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! (227 reviews)
This is a classic luxury hotel. I can't imagine the amount of time and energy it takes to upkeep this property. But they somehow manage to maintain a spotless, manicured and warm environment. The room was quite large and rich in design. The restaurant and the staff who work there are excellent. I ...

Reviewed on 9 October 2025

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Villa di Piazzano - Small Luxury Hotel of the World
Hotel San Michele

Hotel San Michele

4 out of 5
Via Guelfa 15, Cortona, AR
9/10 Wonderful! (268 reviews)
Very friendly and helpful staff. Nice rooms

Reviewed on 7 September 2025

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Hotel San Michele
See all 1,292 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

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