Cortona Holidays from AU$3,569
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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.
The Latest Cortona Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Hotel La Scaletta Al Ponte Vecchio
Historic Centre of Florence
AU$3,569
per person
16 Dec - 23 Dec
found 24 hours ago
Return flight included
Brisbane (BNE) to Florence (FLR)
9/10 Wonderful! (1,002 reviews)
Hotel La Scaletta exceeded our expectations! Everything about the property - location, amenities, breakfast, room, and helpful staff - was excellent. I had stayed in the hotel (and loved it) decades before but it has ascended from a pensione to a true hotel. I hope to return one day!
Reviewed on 2 Oct 2026
Grand Hotel Cavour
Historic Centre of Florence
AU$3,929
per person
16 Dec - 23 Dec
found 24 hours ago
Return flight included
Brisbane (BNE) to Florence (FLR)
9.4/10 Exceptional! (1,000 reviews)
Staff was friendly and accommodating! Rooms were very clean and SPACIOUS!
Would definitely return!
Reviewed on 5 Oct 2026
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$1,012
15 Oct - 16 Oct
includes taxes & fees
9.8/10 Exceptional! (253 reviews)
"Stunning property; a real representation of Tuscany with the long driveway of tall trees; staff was amazing; food was excellent; gardens, picturesque! We would highly recommend! Overall amazing !!!"
Reviewed on 5 Oct 2026
Monastero di Cortona Hotel & Spa
Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
AU$437
25 Oct - 26 Oct
includes taxes & fees
10/10 Exceptional! (346 reviews)
"Beautiful experience. Would recommend again and again."
Reviewed on 6 Oct 2026
Il Falconiere - Relais e Chateaux
Localita San Martino 370 Cortona AR
AU$613
2 Nov - 3 Nov
includes taxes & fees
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.
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.
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.
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.
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.
San Domenico Church
9.0/10 (9 reviews)
After visiting San Domenico Church, make a plan to see the other sights and activities in Cortona. Make time to visit the cathedral and monuments while you're in the area.
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.
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.
What to do in Cortona
Montepulciano Wine Tasting in the Tuscan Countryside
AU$40
per adult
Montepulciano: Tuscan Cooking Class with Fresh Pasta & Wine
AU$129
per adult
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
AU$176
per adult
98% of travellers recommend
Frequently asked questions
How much does a Cortona holiday package cost?
You'll find cheap prices from AU$3,569 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.
