Cortona Holidays
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Your Cortona Holiday
Book a Cortona holiday package and prepare to experience the highlights of this city. Think about staying in the neighbourhood of Contrada Castello, which is great for dining, views and culture. Make your trip to Cortona even more fulfilling by going sightseeing. Villa Bramasole, Cathedral of Cortona and Piazza della Repubblica are among the major attractions you'll want to explore. A few clicks is all it takes to put together the ultimate Cortona holiday on Expedia.
Cortona Holiday
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 |
Our pick of the best Cortona Hotel Deals
Villa di Piazzano - Small Luxury Hotel of the World
Localita Piazzano, C.P. 6 Cortona AR
AU$1,102
29 Aug - 30 Aug
includes taxes & fees
9.8/10 Exceptional! (245 reviews)
"Staff was helpful , and the room was clean. The Antica Casina di Caccia dining with wine pairing was absolutely amazing. Also took some great pictures in the garden. The breakfast was nice too."
Reviewed on 17 Aug 2026
Monastero di Cortona Hotel & Spa
Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
AU$531
3 Sept - 4 Sept
includes taxes & fees
10/10 Exceptional! (315 reviews)
"Amazing!!!! Very well kept place, the staff treats you like family. Room was cleaned fast in the morning. Restaurant and bar staff as well were amazing. The pool area is good vibes and the drinks and really good too 👍👍 I would definitely come back."
Reviewed on 21 Aug 2026
Il Falconiere - Relais e Chateaux
Localita San Martino 370 Cortona AR
AU$849
26 Aug - 27 Aug
includes taxes & fees
9.4/10 Exceptional! (138 reviews)
"Beautiful property and location."
Reviewed on 14 Aug 2026
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.
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.
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.
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.
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.
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.
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.
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.
What to do in Cortona
Tasting Tour in One of The Most Beautiful Cellars in the World
AU$54
per adult
100% of travellers recommend
Montepulciano Wine Tasting in the Tuscan Countryside
AU$41
per adult
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
AU$153
per adult
98% of travellers recommend
Frequently asked questions
How much does a Cortona holiday package cost?
You'll find cheap prices 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?
- 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.
- 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.
- 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.
- 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.
