Cortona Holidays

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Top Flight + Hotel Deals in Cortona

Price found within the past 48 hours. Click for updated prices.
Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

Historic Centre of Florence
€436
per person
28 Sept - 30 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
9/10 Wonderful! (1,006 reviews)
We had a wonderful stay at La Scaletta in Florence! The hotel was extremely clean, and the staff was always friendly, welcoming, and very helpful throughout our stay. The location is fantastic, just steps from the Ponte Vecchio, with so many great shops, restaurants, and beautiful sights within easy walking distance. One of the things we loved most was the combination of history and modern comfort. Staying in such a beautiful historic building, surrounded by gorgeous frescoes and architectural details, made the experience feel very special, while the rooms still had a fresh, modern vibe. The terrace bar was another highlight and a wonderful place to relax and enjoy Florence. Beautiful hotel, excellent location, and great service. We would definitely recommend La Scaletta and would happily stay here again!

Reviewed on 12 Aug 2026

Aurum Uffizi

Aurum Uffizi

Historic Centre of Florence
€566
per person
23 Oct - 28 Oct
found 1 day ago
Return direct flight included
Athens (ATH) to Florence (FLR)
7.6/10 Good! (1,003 reviews)
Clean room, convenient location. has AC and lift. Breakfast was ok. Would stay again

Reviewed on 12 Aug 2026

Aurum Firenze

Aurum Firenze

Historic Centre of Florence
€606
per person
23 Oct - 28 Oct
found 1 day ago
Return direct flight included
Athens (ATH) to Florence (FLR)
7.4/10 Good! (1,008 reviews)
Room very small, no chairs inside, ants everywhere, including the breakfast area. Quadruple room has a double bed and a single bed, apparently this was the biggest room in the hotel. We book for 4 people ( 2 adults and 2 children 12 and 16 and they had to squeeze in a single bed.

Reviewed on 12 Aug 2026

Grand Hotel Cavour

Grand Hotel Cavour

Historic Centre of Florence
€1,013
per person
25 Oct - 30 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
9.2/10 Wonderful! (1,001 reviews)
Fantastic location, lovely rooftop terrace - my only comment would be that the rooms need somewhere to sit down.

Reviewed on 13 Aug 2026

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

Historic Centre of Florence
€812
per person
23 Oct - 28 Oct
found 1 day ago
Return direct flight included
Athens (ATH) to Florence (FLR)
9.6/10 Exceptional! (580 reviews)
Stunning hotel and maintained to a spotless standard. Bit of a trek to the centre and parking not cheap but good services just outside (tram, bus) - just takes some working out. We probably didn't need to go for the suite considering the time of year (Sauna and jacuzzi not overly used after stomping streets in near 40deg heat!). Breakfast good and staff super friendly/informative.

Reviewed on 11 Aug 2026

Things to do in and around Cortona

Cortona, nestled in the heart of Tuscany, is ideal for a romantic getaway, offering stunning outdoor scenery and a plethora of activities. Visitors can indulge in rejuvenating spa treatments, explore charming theatre performances, and embark on custom tours or day trips to discover the region's rich history. Outdoor adventures abound, making Cortona a perfect destination for those seeking both relaxation and exploration.

Shopping

Cortona offers a delightful shopping experience with local shops and boutiques. For a larger selection, visit Valdichiana Outlet Village, located 16.1km away, featuring a vibrant mix of shops. If you're up for a drive, explore RI Crea RE and Maioliche Nulli, both offering unique Italian goods further afield.

Recreation

At Tennis Club Castiglionese, indulge in a luxurious atmosphere while enjoying a game of tennis amidst beautiful countryside. Experience the charm of Signorelli Theatre, where culture and romance blend seamlessly. For outdoor enthusiasts, Golf Club Valdichiana offers a splendid golfing experience surrounded by stunning landscapes.

Adventure

Experience the fun at Tavernelle Aquatic Park, a vibrant waterpark 32.2km from Cortona, perfect for families and adventure seekers. For a thrilling zipline experience, visit Saltalbero Adventure Park, also 32.2km away. Additionally, embark on Hannibal's Journey, a scenic hiking trail located 8.0km from Cortona.

Nightlife

Cortona's nightlife offers a charming blend of wine bars and cosy trattorias. Enjoy a glass of local Chianti at Enoteca Nottola or savour traditional Tuscan dishes at La Bucaccia. For a lively atmosphere, visit Bar Signorelli, where locals gather for drinks and conversation under the 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, is ideal for romantic getaways and outdoor adventures, boasting stunning scenery. Explore its captivating churches, picturesque piazzas, and nearby lakes, which cater to culture enthusiasts and city explorers alike. With a wealth of attractions and experiences, Cortona offers a delightful blend of history and natural beauty, making it a perfect destination for those seeking a unique Italian escape.

  • Lake Trasimeno: Experience the serene beauty of Lake Trasimeno, located 17.7km from Cortona. This picturesque lake offers a perfect setting for outdoor activities, romantic strolls, and relaxing beach vibes, surrounded by lush scenery.
  • Farneta Abbey: Nestled within Cortona, Farneta Abbey is a cultural gem that showcases stunning architecture and a tranquil atmosphere. Visitors can immerse themselves in its rich history and appreciate the serene environment ideal for reflection.
  • Guglielmi Castle: Situated 14.5km from Cortona, Guglielmi Castle boasts captivating views and a romantic ambiance. Explore its historical significance and enjoy the beautiful landscapes that surround this enchanting fortress.

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.

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
€677
17 Aug - 18 Aug
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
€292
23 Aug - 24 Aug
includes taxes & fees
10/10 Exceptional! (309 reviews)
"Hotel was perfect. Price was a bit high and very difficult parking"

Reviewed on 16 Aug 2026

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

Il Falconiere - Relais e Chateaux

Localita San Martino 370 Cortona AR
€521
27 Aug - 28 Aug
includes taxes & fees
9.4/10 Exceptional! (138 reviews)
"Beautiful property and location."

Reviewed on 14 Aug 2026

Il Falconiere - Relais e Chateaux
See all 1,173 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.

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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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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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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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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Eremo Le Celle

9.4/10 (12 reviews)
St. Francis of Assisi founded this rustic stone hermitage in 1211, offering a glimpse into Franciscan monastic life. Wander the peaceful cells and chapels amid the serene woodland setting.
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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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Casali Palace

8.6/10 (7 reviews)
This Renaissance palace anchors Cortona's historic centre with its distinctive stone façade. Wander through the surrounding cobblestone streets to discover authentic Tuscan charm in this hillside town.
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What to do in Cortona

Montepulciano Gran Tour

Montepulciano Gran Tour

€15
per adult
Montepulciano Gran Tour
3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch

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

€94
per adult
98% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
Chianciano Terme: Sensory Spa Admission Ticket

Chianciano Terme: Sensory Spa Admission Ticket

€55
per adult
Chianciano Terme: Sensory Spa Admission Ticket
See all activities in Cortona

Frequently asked questions

How much does a Cortona holiday package cost?
You'll find cheap prices from €436 on Expedia for your Cortona break. However, factors like the season, length of stay and your choice of hotel will influence how much your holiday to Cortona costs.
What are the cheapest months to go to Cortona?
If you'd like to snag a cheap Cortona holiday package, consider travelling in December, January and February. You're likely to find better prices on airfares and hotels during these months — perfect for travellers wishing to save money.
How many days is enough for Cortona?
With around 3 days, you'll have enough time to enjoy popular neighbourhoods like Cortona Old Town and Sodo during your Cortona holiday. Be sure to also add Palazzo Comunale and Museum of the Etruscan Academy to your must-see list. Searching for more adventures? Consider exploring outside of Cortona on tours and day trips.
Is it worth booking a holiday package to Cortona?
Popular for its views, dining and walking trails, a Cortona holiday is a hit with all kinds of visitors. Be sure to check out top sights like Villa Bramasole and Piazza della Repubblica, and consider renting a set of wheels for day trips to discover even more.
How to find the best Cortona package deals?
Start your search for a Cortona package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply a few filters, like "Property type" and "Popular locations," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Cortona package deal straight away, simply switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Cortona escape underway.
Is it cheaper to book a Cortona holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to arranging flights and stays individually. Better still, you can customise your Cortona trip to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a holiday package to Cortona?
If you're considering an impromptu Cortona holiday, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can land terrific deals on your flights and hotels by booking well in advance.
How to plan a trip to Cortona?
  1. Choose when to go: Check your calendar and get packing. Your favourite season and the type of activities available will also help you decide when to escape to Cortona.
  2. Budget wisely: Besides the price of your stay, you'll need to factor in other expenses too. These include food, transportation and flights. Also, set aside some extra funds for unexpected costs that could crop up during your trip to Cortona.
  3. Work out your trip length: Think about how much time you'd like to spend discovering Cortona. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Bundle your accommodation and airfare: Once you've nailed down your dates and duration, book the right Cortona holiday package for you.

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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.