Cortona Holidays from £396

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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.
Hotel Ginori al DUOMO

Hotel Ginori al DUOMO

Historic Centre of Florence
Save 100% on your flight
£396
per person
12 Nov - 17 Nov
found 1 day ago
Return flight included
London (LGW) to Florence (FLR)
8.8/10 Excellent! (61 reviews)
Fantastic stay, thank you for the upgrade, spacious, cool rooms. Great location, walk to the station and across the road is a convenience store and great restaurants and gelato in the same street

Reviewed on 4 Sept 2026

Aurum Uffizi

Aurum Uffizi

Historic Centre of Florence
Save 100% on your flight
£463
per person
26 Oct - 30 Oct
found 18 hours ago
Return flight included
London (LCY) to Florence (FLR)
7.6/10 Good! (1,001 reviews)
Aurum Firenze

Aurum Firenze

Historic Centre of Florence
Save 100% on your flight
£482
per person
26 Oct - 30 Oct
found 18 hours ago
Return flight included
London (LCY) to Florence (FLR)
7.6/10 Good! (1,003 reviews)
Brilliant location, no more than 15-20 maximum minutes to walk to all the main sites. The staff worked hard and were very friendly and helpful.

Reviewed on 17 Sept 2026

Villa Neroli

Villa Neroli

Coverciano
Save 100% on your flight
£465
per person
24 Oct - 31 Oct
found 1 day ago
Return flight included
Edinburgh (EDI) to Florence (FLR)
9.6/10 Exceptional! (659 reviews)
My cousin and I were on a month trip with many stops in 4 countries. Florence was our 2nd last stop. Villa Nerolli was my favorite overall stay. It was so very relaxing with the scents of roses, bamboo, jasmine and wisteria everywhere. Simply beautiful and a symphony for all the senses. The food, service, pool, and drinks were fabulous 💖 I hope to make it back one day 🙏

Reviewed on 15 Sept 2026

Relais Uffizi, Tailor made Hotel

Relais Uffizi, Tailor made Hotel

Historic Centre of Florence
Save 100% on your flight
£725
per person
20 Oct - 24 Oct
found 1 day ago
Return flight included
London (LGW) to Florence (FLR)
9.2/10 Wonderful! (161 reviews)
LOVE this hotel! Perfect location, amazing breakfast, fantastic staff, beautiful rooms, excellent bathrooms. Made our Florence trip amazing highlight of our time in Italy!

Reviewed on 15 Sept 2026

Things to do in and around Cortona

Cortona offers a perfect blend of romance and outdoor adventure, making it an ideal destination for scenic vacations. Visitors can indulge in spa treatments, explore local theatres, and embark on custom tours. The charming town also provides exciting day trips to nearby attractions, ensuring there's something for everyone to enjoy while soaking in the stunning Tuscan landscape.

Shopping

In Cortona, you can shop for souvenirs at local boutiques and artisan shops. If you're up for a drive, visit Valdichiana Outlet Village, 16.1km away, for a variety of brands and family-friendly entertainment. For more options, RI Crea RE and Maioliche Nulli are located 21 and 46.7km away, respectively.

Recreation

Golf Club Valdichiana, situated 14.5km from Cortona, offers a scenic golfing experience amidst stunning landscapes. Enjoy the sport in a vibrant outdoor setting. Alternatively, Tennis Club Castiglionese, located 8.0km away, provides a luxurious atmosphere for tennis enthusiasts, perfect for relaxation and recreation.

Adventure

At Tavernelle Aquatic Park, located 32.2km from Cortona, enjoy thrilling water slides and family-friendly attractions. For a scenic hike, embark on Hannibal's Journey, a captivating trail 8.0km away, offering stunning outdoor views. For speed enthusiasts, the Magione Racetrack, 25.7km away, promises exhilarating motor racing experiences.

Nightlife

Cortona's nightlife is charming and relaxed, featuring quaint wine bars and lively piazzas. Enjoy a glass of local wine at Bar D'Angelo or savour traditional cuisine at La Bucaccia. For a more vibrant atmosphere, explore the bars along Via Nazionale, where locals and tourists mingle under the Tuscan stars.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Cortona

Cortona, a charming Italian town in Tuscany, offers a romantic and scenic getaway perfect for outdoor enthusiasts. Explore its rich culture through captivating churches, vibrant piazzas, and intriguing museums. With attractions that cater to those seeking a blend of city experience and stunning landscapes, Cortona promises an enriching vacation filled with delightful discoveries. Whether wandering through its historic streets or enjoying the breathtaking views, this picturesque destination is sure to leave a lasting impression.

  • Lake Trasimeno: Located 17.7km from Cortona, Lake Trasimeno offers stunning scenery and romantic beaches. Ideal for outdoor activities, you can enjoy leisurely strolls, picnics by the water, or even take a boat trip to soak in the tranquil atmosphere.
  • Villa Bramasole: Nestled within Cortona, Villa Bramasole is a historic gem that embodies the rich culture of the region. This enchanting villa, made famous by Frances Mayes’ book Under the Tuscan Sun, invites visitors to explore its beautiful gardens and appreciate its architectural charm.
  • Isola Maggiore: Just 14.5km from Cortona, Isola Maggiore is a picturesque island perfect for outdoor adventures. Enjoy the serene beaches, take a leisurely hike, or explore the charming village atmosphere, offering a delightful escape from the mainland.

Best time to go to Cortona

The best time to visit Cortona can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Cortona falls in July, when visitor numbers are slightly high and weather is sunny with no rain. The coolest average temperature in Cortona falls in January, visitor numbers are slightly low and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January39.2°F (4.0°C)Light RainMostly CloudySlightly LowSlightly Low
February41.2°F (5.1°C)Light RainMostly SunnySlightly LowSlightly Low
March46.0°F (7.8°C)Light RainMostly SunnyAverageSlightly Low
April52.7°F (11.5°C)Light RainMostly SunnySlightly HighAverage
May59.5°F (15.3°C)Light RainMostly SunnyAverageAverage
June69.1°F (20.6°C)Light RainMostly SunnyAverageSlightly High
July74.8°F (23.8°C)No RainSunnySlightly HighSlightly High
August74.5°F (23.6°C)No RainSunnySlightly HighSlightly High
September65.7°F (18.7°C)Light RainMostly SunnyAverageAverage
October56.8°F (13.8°C)Light RainMostly SunnyAverageAverage
November48.6°F (9.2°C)Light RainMostly SunnyAverageAverage
December41.7°F (5.4°C)Light RainMostly SunnySlightly LowAverage

Tips to save on your trip to Cortona

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Cortona.
  • Consider traveling during the off-peak season (typically January to March) for more affordable package holidays to Cortona.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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

Localita Piazzano, C.P. 6 Cortona AR
£539
30 Sept - 1 Oct
includes taxes & fees
Villa di Piazzano - Small Luxury Hotel of the World
Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
£301
27 Sept - 28 Sept
includes taxes & fees
10/10 Exceptional! (332 reviews)
"I cannot say enough great things about our stay at the Monastery. The property is gorgeous and clean, the staff were beyond helpful and the food was incredible! The spa baths were also so relaxing. We did not want to leave this hotel. I’d like to specifically call out Frederico with the glasses, ..."

Reviewed on 17 Sept 2026

Monastero di Cortona Hotel & Spa
Il Falconiere - Relais e Chateaux

Il Falconiere - Relais e Chateaux

Localita San Martino 370 Cortona AR
£371
19 Oct - 20 Oct
includes taxes & fees
9.4/10 Exceptional! (143 reviews)
"Il Falconiere treats you as a true guest. Welcoming, courteous and professional were all staff members. Food truly excellent and with the Michelin star, you will enjoy a sumptuous meal, ample portions, amuse bouche at meal's start with a surprise dessert tray with little bites. All staff you interact ..."

Reviewed on 10 Sept 2026

Il Falconiere - Relais e Chateaux
See all 1,186 properties in Cortona
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Stay near popular Cortona attractions

Villa Bramasole

9.2/10 (20 reviews)
Made famous by "Under the Tuscan Sun," Villa Bramasole showcases classic Tuscan architecture. Admire this private residence from the road during a scenic walk through Cortona's charming countryside.
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Piazza della Repubblica

9.4/10 (95 reviews)
Piazza della Repubblica pulses as Cortona's medieval heart, framed by the Palazzo Comunale and its clock tower. Savour authentic Tuscan cuisine at outdoor cafés while absorbing panoramic countryside views.
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Cortona Cathedral

9.4/10 (77 reviews)
This Romanesque-Renaissance cathedral stands on ancient Roman temple remains, showcasing elegant portals and slender columns. Inside, experience serenity while admiring panoramic views of the Tuscan countryside.
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Santa Margherita Basilica

9.2/10 (30 reviews)
Perched high above Cortona, this Gothic-Baroque basilica houses Saint Margaret's remains, the town's patron saint. Visitors can admire the silver urn and enjoy sweeping Tuscan countryside views.
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Santa Maria Nuova

8.8/10 (5 reviews)
This Renaissance masterpiece by Giorgio Vasari features a striking central dome and Greek cross plan just outside Cortona's walls. Enjoy the serene atmosphere while taking in panoramic views of the Tuscan countryside.
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Fortress of Girifalco

8.8/10 (25 reviews)
You can find out about the history of Cortona with a trip to Fortress of Girifalco. You can enjoy the wineries while in the area.
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Palazzo Comunale

9.2/10 (44 reviews)
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.
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Signorelli Theatre

9.2/10 (14 reviews)
You can enjoy a show at Signorelli Theatre on your trip to Cortona. Discover the area's countryside and monuments.
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What to do in Cortona

Montepulciano Gran Tour

Montepulciano Gran Tour

£13
per adult
Montepulciano Gran Tour
Montepulciano: Winery Tour and Tasting

Montepulciano: Winery Tour and Tasting

£30
per adult
100% of travellers recommend
Montepulciano: Winery Tour and Tasting
Oil museum and oil mill in Tuscany: tour and tasting

Oil museum and oil mill in Tuscany: tour and tasting

£17
per adult
Oil museum and oil mill in Tuscany: tour and tasting
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.

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* 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.