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.
Grand Hotel Cavour
Historic Centre of Florence
CA $1,737
per person
Nov 22 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9.2/10 Wonderful! (1,004 reviews)
Lovely hotel and great position in Florence. Staff were friendly and helpful. Breakfast was lovely plenty of choice. Wouldn’t hesitate to stay there again. Perfect for the usual sightseeing !
Reviewed on Sep 15, 2026
The Moon Boutique Hotel & Spa
Historic Centre of Florence
CA $2,385
per person
Oct 24 - Oct 28
found 5 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Florence (FLR)
9.6/10 Exceptional! (592 reviews)
Great location. We suggest taking the river down to the city center every day. The free breakfast and coffee is great way to start your day. Schedule a spa day at least once so you can relax before the walk to dinner! Reception was super nice and even helped us call a taxi.
Reviewed on Sep 21, 2026
Hotel La Scaletta Al Ponte Vecchio
Historic Centre of Florence
CA $2,386
per person
Oct 22 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9/10 Wonderful! (1,005 reviews)
I would say this is a 3.5 star property. The room was clean but basic, same for the bathroom and amenities like soap etc. the location is very central but the room was still quiet. There is no concierge and the staff was not able to make any reservations for us.
Reviewed on Sep 19, 2026
Hotel degli Orafi
Historic Centre of Florence
CA $2,129
per person
Oct 24 - Oct 28
found 5 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Florence (FLR)
9.6/10 Exceptional! (1,002 reviews)
The hotel was right beside the Uffizzi museum and steps from the Ponte Vecchio. The front desk staff were extremely friendly and helpful, providing a map with walking distances to major attractions and recommending less busy sights to see. They will also recommend some excellent local restaurants for you to try authentic Florentine cuisine and make the reservation for you. Rooms were comfortable and clean with little touches like chocolates every night in your room. The included breakfast was amazing with many choices for both European and North American guests. Highly recommend this hotel
Reviewed on Sep 18, 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 $906
CA $1,010 total
Sep 30 - Oct 1
includes taxes & fees
9.8/10 Exceptional! (250 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 $504
CA $568 total
Oct 11 - Oct 12
includes taxes & fees
10/10 Exceptional! (335 reviews)
"There was nothing to be improved because everything was perfection!!"
Reviewed on Sep 19, 2026
Il Falconiere - Relais e Chateaux
Localita San Martino 370 Cortona AR
CA $621
CA $696 total
Oct 22 - Oct 23
includes taxes & fees
9.4/10 Exceptional! (144 reviews)
"Amazing stay for our 25th anniversary. The property is breathtaking and every corner was like a Tuscan postcard! The room was beautiful, the pools were great and the food was exceptional. Would highly recommend and would go back in a second!"
Reviewed on Sep 18, 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.
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.
Santa Maria Nuova
8.8/10 (5 reviews)
Find out about the history of Cortona when you take a trip to Santa Maria Nuova. You can enjoy the wineries while in the area.
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.
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.
Signorelli Theatre
9.2/10 (14 reviews)
You can make plans for a show at Signorelli Theatre during your stay in Cortona. Discover the area's countryside and monuments.
What to do in Cortona
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
CA $136
per adult
98% of travellers recommend
Oil museum and oil mill in Tuscany: tour and tasting
CA $32
per adult
Montepulciano: Artisan Heroic Wine Tasting at the Terrace
CA $81
per adult
Frequently asked questions
How much does a Cortona vacation package cost?
You'll find cheap prices from CA $1,737 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.
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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.
