Cortona Holidays from £487

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Your Cortona Holiday

With plenty of highlights as well as hidden gems, this city is best experienced with a Cortona holiday 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 holiday is only clicks away with Expedia.

Top Cortona Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
25 Sept - 28 Sept
found 1 day ago
Return flight included
London (LHR) to Florence (FLR)
9.6/10 Exceptional! (462 reviews)
Hands down the best place we have stayed. They accommodated to go breakfasts for our tours, arranged taxis, made cappuccino when we were heading out the door. Wonderful experience

Reviewed on 6 Jun 2025

Grand Hotel Cavour

Grand Hotel Cavour

4 out of 5
Historic Centre of Florence
per person
22 Sept - 27 Sept
found 1 day ago
Return flight included
London (LGW) to Florence (FLR)
9.2/10 Wonderful! (1,003 reviews)
Wonderful location, near Duomo. We had two rooms- both well appointed.staff was kind and helpful- made dinner reservations for us.

Reviewed on 5 Jul 2025

Hotel Bencista

Hotel Bencista

3 out of 5
per person
5 Aug - 9 Aug
found 2 hours ago
Return flight included
London (LGW) to Florence (FLR)
7.2/10 Good! (12 reviews)
Cappuccina Country Resort

Cappuccina Country Resort

4 out of 5
per person
16 Sept - 23 Sept
found 1 day ago
Return flight included
London (LON) 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 28 May 2025

Porta al Prato

Porta al Prato

4 out of 5
Santa Maria Novella
per person
16 Sept - 23 Sept
found 1 day ago
Return flight included
London (LON) to Florence (FLR)
8.8/10 Excellent! (152 reviews)
Clean rooms and property Staff very friendly and helpful

Reviewed on 13 Jun 2025

Cortona Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Population
2,200
Max Temp Winter
7ºC
Max Temp Summer
27ºC
Top Sights
Cathedral of Cortona, Signorelli Theatre and San Luciano Winery

Top hotels in Cortona

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
Fully refundableReserve now, pay when you stay
The price is £474 per night from 10 Jul to 11 Jul
£474
10 Jul - 11 Jul
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 24 Jun 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 £277 per night from 27 Jul to 28 Jul
£277
27 Jul - 28 Jul
includes taxes & fees
9.8/10 Exceptional! (214 reviews)
Fantastic!
"It’s impossible to praise this hotel enough! What an amazing experience, from the care and concern after booking, to check-in and the attention to detail throughout our stay. The location is good, not too far to walk to local restaurants in Cortona but far enough to be tranquil. The hotel is spotless ..."

Reviewed on 30 Jun 2025

Monastero di Cortona Hotel & Spa
Il Falconiere - Relais e Chateaux
Il Falconiere - Relais e Chateaux
5 out of 5
Localita San Martino 370, Cortona, AR
Fully refundableReserve now, pay when you stay
The price is £324 per night from 17 Jul to 18 Jul
£324
17 Jul - 18 Jul
includes taxes & fees
9.2/10 Wonderful! (106 reviews)
"Very pretty property and amenities"

Reviewed on 30 Jun 2025

Il Falconiere - Relais e Chateaux
See all 1,315 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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Popular places to visit

Villa Bramasole

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

Villa Bramasole

Palazzo Comunale

Palazzo Comunale 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 theatre.

Palazzo Comunale

San Domenico Church

You can learn about the history of Cortona with a stop at San Domenico Church. Experience the area's museums and musical theatre.

San Domenico Church

What to do in Cortona

For your personal cooking class in Tuscany

Amazing four courses cooking class in Tuscany

£227
per adult
Amazing four courses cooking class in Tuscany
Cortona

Cortona Private Guided Tour

£223
per traveller
Cortona Private Guided Tour
3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch

From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch

£98
per adult
100% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
See all activities in Cortona

Frequently asked questions

Why should I book my Cortona holiday with Expedia?
Expedia has your back for every detail of your Cortona getaway. You'll always get the best prices, but when you bundle your accommodation, airfares and/or car hire into a holiday package, you'll get even more savings. Want to really make the most of your break? Add some activities and tours to your package. We offer flexible cancellation policies on most bookings, so there's no need to worry if your plans change. Head over to our Customer Service Portal link to discover more.
When is the best time of year to holiday in Cortona?
Peak season falls in April, May and June and is an exciting time to visit --- if you don't mind the crowds. October, November and December are generally quieter times of the year. To give you an idea of the type of weather to expect, the average daytime temperature in January, the coolest time of year in Cortona, is 3ºC. The warmest time here is July, when temperatures reach an average of 23ºC.
What are the top hotels for my holiday in Cortona?
Travellers heading to Cortona often stay in Cortona Old Town. Hotel San Luca and Monastero di Cortona Hotel & Spa are favourites in this neighbourhood. But it's not the only exciting place around town! Fratticciola is another terrific area and where you'll find Cortona Resort - Le Terre Dei Cavalieri and Hotel Italia.
How do I get a cheap holiday to Cortona?
Combine your hotels and flights, add extras such as activities or a hire car, and save with a Cortona holiday. You won't just score awesome discounts on your adventure --- you'll have a world of choice too. When you book with Expedia, you can choose from more than 400 partner airlines and 321,000 properties around the world. Your next epic adventure starts right here, right now! Learn more about how you can save money on your holiday when you combine your flight and hotel bookings with Expedia.
What should I do on my Cortona holiday?
There are so many places to visit while having a holiday in Cortona. Villa Bramasole, Cathedral of Cortona, Piazza della Repubblica and Belvedere are a few of this city's most popular attractions.
What is the best area to stay in when on holiday in Cortona?
An escape to Cortona isn't complete without paying a visit to Villa Bramasole. Why not book a stay close to this popular attraction?
Do I need a visa for my Cortona holiday?
Look up the most up-to-date information on official government websites. Your nationality and whether you're travelling for business, leisure or study will determine if you require a visa for Cortona. Make yourself familiar with the application process, including the required documentation, fees and turnaround times. Finalise your application well in advance to allow sufficient time for processing. Some visas may take many weeks or even months to obtain, depending on the country and time of year.
What should I wear on my Cortona holiday?
Do some research into the sorts of things people in Cortona wear, and maybe even browse social media fashion pages for inspiration. Try to create a versatile wardrobe full of pieces that work for your destination and show off your personal style. Pack your bags with confidence by looking up the weather conditions in Cortona. July brings the warmest temperatures, with daily averages of 23ºC, while January days average 3ºC, making it the coolest time of year.
What does an Expedia Cortona holiday include?
Hotels, car hires and flights, or any combination of the three --- it's your pick! Whether you're headed to Cortona with the entire family or travelling by yourself, there's a package to match every budget and style. Once you've made your booking, why not add on some tours and experiences? Villas and apartments are a couple of popular property types in Cortona. Whatever your group size or holiday style, you can rely on Expedia for the flexibility and freedom to customise your dream escape.
Does Expedia offer Book Now, Pay Later Cortona holidays?
We sure do. Expedia has teamed up with online lender Klarna to help you easily pay for your trip in manageable instalments. Simply click on the payment plan that suits best during the checkout process and take away the stress of budgeting for your trip. Don't forget to bundle your flights, car hire and hotel with Expedia to get the biggest bang for your holiday buck. Consider these flexible payment options below:

  • Pay monthly holidays: If paying small amounts each month works for you, Klarna can help. Paying in convenient monthly instalments will make that dream holiday possible.
  • No-deposit holidays: When you come across an unbeatable deal but your budget doesn't quite go that far, Klarna's no-deposit holiday plan will allow you to Book Now, Pay Later to get what you want.

Can I choose my airline with a Cortona Expedia holiday?
You can, and with more than 400 airlines to choose from throughout the world, you've got lots of choice. Search the available options and see which airline best fits your needs and budget.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.