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.
The Moon Boutique Hotel & Spa
Historic Centre of Florence
CA $1,436
per person
Nov 4 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.6/10 Exceptional! (584 reviews)
All the staff were amazing and helpful! The kitchen staff for breakfast catered for all out needs. The spa was excellent too and I’d highly recommended this hotel to anyone. It’s in a Great location with good links to the airport and tourist spots across the city.
Reviewed on Aug 29, 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 $884
CA $985 total
Sep 2 - Sep 3
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 Aug 17, 2026
Monastero di Cortona Hotel & Spa
Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
CA $481
CA $542 total
Sep 13 - Sep 14
includes taxes & fees
10/10 Exceptional! (319 reviews)
"The hotel was amazing and the staff very friendly and helpful. The breakfast was spectacular. we really enjoyed ourselves at this hotel and in the city of Cortona."
Reviewed on Aug 30, 2026
Il Falconiere - Relais e Chateaux
Localita San Martino 370 Cortona AR
CA $777
CA $868 total
Sep 29 - Sep 30
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)
You can learn about the history of Cortona with a trip to Villa Bramasole. You can enjoy the wineries while 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.
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.
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.
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.
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.
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.
What to do in Cortona
Tasting Tour in One of The Most Beautiful Cellars in the World
CA $53
per adult
100% of travellers recommend
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
Frequently asked questions
How much does a Cortona vacation package cost?
You'll find cheap prices from CA $1,321 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.
