Cortona Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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 Villa Liana

Hotel Villa Liana

3 out of 5
Historic Centre of Florence
Price was CA $1,743, price is now CA $1,125 per person
CA $1,125
per person
Aug 18 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
8.6/10 Excellent! (354 reviews)
clean, spacious, well-stocked with toiletries and breakfast items too. walkable distance to all iconic sites. Grace, the breakfast host, did an incredible job, very welcoming & served with options for hot coffee drinks. All together, wonderful, memorable stay!!

Reviewed on May 23, 2026

Donati Luxury Tower Suites

Donati Luxury Tower Suites

5 out of 5
Historic Centre of Florence
Price was CA $5,314, price is now CA $3,288 per person
CA $3,288
per person
Aug 18 - Aug 24
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.8/10 Exceptional! (68 reviews)
Agradable estancia. Excelente servicio. La habitación la mantenían siempre limpia. Todo queda cerca del área. Muy recomendable

Reviewed on May 23, 2026

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Price was CA $2,637, price is now CA $1,636 per person
CA $1,636
per person
Sep 5 - Sep 10
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Florence (FLR)
7.4/10 Good! (1,014 reviews)
It was not entirely clean, the staff don't do much. Breakfast is from the day before. Air conditioning excellent.

Reviewed on Jul 3, 2026

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Price was CA $4,795, price is now CA $2,987 per person
CA $2,987
per person
Aug 12 - Aug 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9.6/10 Exceptional! (147 reviews)
It’s a beautiful property, but be aware that it is secluded and that the restaurant menu is quite limited and after a couple of days, we were happy to go elsewhere. The waiting staff was attentive and nice, front desk not as much (maybe the la guard barrier?)

Reviewed on Jun 19, 2026

Hotel Palazzo San niccolò & Spa

Hotel Palazzo San niccolò & Spa

4 out of 5
Price was CA $2,068, price is now CA $1,295 per person
CA $1,295
per person
Aug 5 - Aug 11
found 11 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
9.2/10 Wonderful! (187 reviews)
This was a little slice of heaven and such a hidden gem. This place is by far my favorite that I have been to in Europe

Reviewed on Jun 16, 2026

Ready to book your vacation to Cortona?

 

Choose your dates

Cortona Hotel Deals

Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

5 out of 5
Localita Piazzano, C.P. 6 Cortona AR
The price is CA $899 per night from Jul 12 to Jul 13
CA $899
CA $1,002 total
Jul 12 - Jul 13
includes taxes & fees
9.8/10 Exceptional! (238 reviews)
"Staff was so friendly and the property is beautiful"

Reviewed on Jun 28, 2026

Villa di Piazzano - Small Luxury Hotel of the World
Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
The price is CA $463 per night from Jul 12 to Jul 13
CA $463
CA $522 total
Jul 12 - Jul 13
includes taxes & fees
10/10 Exceptional! (290 reviews)
"This is an excellent hotel, great staff, great location and great food. The breakfast is a really nice experience and the courtyard swimming pool is so peaceful."

Reviewed on Jun 29, 2026

Monastero di Cortona Hotel & Spa
Il Falconiere - Relais e Chateaux

Il Falconiere - Relais e Chateaux

5 out of 5
Localita San Martino 370 Cortona AR
The price is CA $666 per night from Jul 30 to Jul 31
CA $666
CA $746 total
Jul 30 - Jul 31
includes taxes & fees
Il Falconiere - Relais e Chateaux
See all 1,196 properties in Cortona
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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.
See properties

What to do in Cortona

3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch

From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch

CA $140
per adult
98% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
Oil museum and oil mill in Tuscany: tour and tasting

Oil museum and oil mill in Tuscany: tour and tasting

CA $32
per adult
Oil museum and oil mill in Tuscany: tour and tasting
Tasting Tour in One of The Most Beautiful Cellars in the World

Tasting Tour in One of The Most Beautiful Cellars in the World

CA $53
per adult
100% of travellers recommend
Tasting Tour in One of The Most Beautiful Cellars in the World
See all activities in Cortona

Frequently asked questions

How much does a Cortona vacation package cost?
You'll find cheap prices from CA $1,125 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.