Cortona Vacation Packages
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Your Cortona Vacation
With plenty of highlights as well as hidden gems, this city is best experienced with a Cortona vacation 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 vacation is only clicks away with Expedia.
Top Cortona Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Duomo Firenze
Historic Centre of Florence
CA $1,378
per person
Dec 8 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.2/10 Wonderful! (1,004 reviews)
Absolutely everything was perfect - from checkin to deprture- Gelato and cookies available all day, wonderful breakfast, room was SO Awesome facing the Duomo, assist to schedule a taxi - lift so less stairs - would absolutely recommend !!!
Reviewed on Oct 2, 2026
The Hoxton, Florence
Historic Centre of Florence
CA $1,729
per person
Dec 10 - Dec 16
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Florence (FLR)
9.4/10 Exceptional! (355 reviews)
This lovely property was a highlight of our stay in Florence for sure. Just out of the rush but still a very close walk to all main attractions. The property is beautifully decorated and maintained and breakfast which we included was wonderful.
Reviewed on Sep 29, 2026
The Moon Boutique Hotel & Spa
Historic Centre of Florence
CA $2,564
per person
Dec 19 - Dec 26
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Florence (FLR)
9.6/10 Exceptional! (600 reviews)
Extremely clean, breakfast service was awesome. Absolutely beautiful room . Shower with steam and jacuzzi settings was wonderful.
Reviewed on Oct 2, 2026
Ready to book your vacation to Cortona?
Cortona Hotel Deals
Villa di Piazzano - Small Luxury Hotel of the World
Localita Piazzano, C.P. 6 Cortona AR
CA $902
CA $1,005 total
Oct 26 - Oct 27
includes taxes & fees
9.8/10 Exceptional! (251 reviews)
"Stunning little hotel with the most beautiful setting, gardens and pool. The room was exceptionally appointed clean. The best part of the stay was the restaurant. The best meals we had on our entire trip. Definitely recommend hiring e-bikes and riding up to Cortona!"
Reviewed on Sep 20, 2026
Monastero di Cortona Hotel & Spa
Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
CA $356
CA $404 total
Oct 25 - Oct 26
includes taxes & fees
10/10 Exceptional! (341 reviews)
"Breakfast was amazing!! Property was not great, but nice!"
Reviewed on Oct 2, 2026
Il Falconiere - Relais e Chateaux
Localita San Martino 370 Cortona AR
CA $511
CA $568 total
Nov 3 - Nov 4
includes taxes & fees
9.4/10 Exceptional! (146 reviews)
"There is nothing to fault here, it’s a perfect hotel. Staff are brilliant, and the buildings and grounds are really well looked after. Breakfast and lunch are ideal too."
Reviewed on Sep 30, 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)
You can learn about the history of Cortona with a trip to Villa Bramasole. You can enjoy the wineries while in the area.
Piazza della Repubblica
9.4/10 (95 reviews)
Find out about the history of Cortona with a stop at Piazza della Repubblica. Make time to visit the cathedral and monuments while you're in the area.
Cortona Cathedral
9.4/10 (77 reviews)
Cortona Cathedral 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 theater.
Fortress of Girifalco
8.8/10 (25 reviews)
You can find out about the history of Cortona when you stop by Fortress of Girifalco. You can enjoy the wineries while in the area.
Santa Margherita Basilica
9.2/10 (30 reviews)
You can learn about the history of Cortona when you stop by Santa Margherita Basilica. Discover the area's museums and cathedral.
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 theater.
Eremo Le Celle
9.4/10 (12 reviews)
Learn about the local history of Cortona when you spend time at Eremo Le Celle. You can enjoy the wineries while in the area.
What to do in Cortona
Montepulciano Wine Tasting in the Tuscan Countryside
CA $40
per adult
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
CA $175
per adult
98% of travellers recommend
Montepulciano: Artisan Heroic Wine Tasting at the Terrace
CA $64
per adult
Frequently asked questions
How much does a Cortona vacation package cost?
You'll find cheap prices from CA $1,378 on Expedia for your Cortona break. However, a range of factors like the season, choice of hotel and length of stay will determine how much your vacation to Cortona costs.
What are the cheapest months to go to Cortona?
December, January and February are the best times to look for cheap Cortona vacation packages. Choosing to travel in less busy months means you can usually find reduced prices on flights and accommodations.
How many days is enough for Cortona?
To get the most out of your Cortona vacation, we suggest staying for 3 days. Split your time between discovering Eremo Le Celle, Belvedere and other leading sights, on top of experiencing neighbourhoods like Cortona Old Town and Sodo. If you've got some spare time, add a day trip to your Cortona vacation itinerary.
Is it worth booking a vacation package to Cortona?
Whether you want to check out top attractions such as Villa Bramasole and Piazza della Repubblica on your Cortona vacation, or coming for its excellent views, dining and walking trails, there's something for everyone here. With so much to see and do, you'll soon discover why so many people think Cortona is a good vacation destination.
How to find the best Cortona package deals?
Bagging a cheap Cortona package deal is a cinch with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget, add some filters and see what's available. You can personalize your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to discover the most affordable Cortona package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Cortona vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll typically land a better deal than booking each component individually. And you'll still have the freedom to create a personalized Cortona vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Cortona?
If you're planning a spontaneous Cortona adventure, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can land sensational deals on your hotels and flights by booking well in advance.
How to plan a trip to Cortona?
- Choose when to get away: Check your calendar and get packing. Your preferred time of year and the activities available will also help you decide when to escape to Cortona.
- Set a budget: Consider expenses like flights, food and transportation when calculating how much to save for your trip to Cortona. Then, select a property that works with your budget, whether that's an affordable stay or a swankier getaway.
- Work out your trip length: Consider how long you'd like to spend exploring Cortona. Plan your days so you can get to all the attractions and experiences you're interested in without rushing.
- Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a customized Cortona vacation package.
Explore a world of travel with Expedia
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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.
