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.
Cappuccina Country Resort

Cappuccina Country Resort

4 out of 5
per person
Aug 17 - Aug 23
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
8.4/10 Very Good! (69 reviews)
We absolutely loved our stay. I wish we got to stay longer. The hotel and the town are so lovely and peaceful. I could have easily stayed there for three days. The staff was so kind. The room was comfortable and very luxurious. Breakfast was yummy.

Reviewed on May 28, 2025

Collegio alla Querce - Auberge Resorts

Collegio alla Querce - Auberge Resorts

5 out of 5
Le Cure
Save 100% on your flight
per person
Aug 17 - Aug 23
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
10/10 Exceptional! (1 review)
Grand Hotel Cavour

Grand Hotel Cavour

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 22 - Sep 28
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9.2/10 Wonderful! (1,003 reviews)
Great location and lovely breakfast.

Reviewed on Jul. 9, 2025

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 18 - Sep 24
found 5 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
7.8/10 Good! (1,000 reviews)
The staff is very friendly.

Reviewed on Jul. 11, 2025

Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 21 - Sep 27
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
8.6/10 Excellent! (462 reviews)
Breakfast was very good and the staff were excellent. Expresso in the morning was on point.

Reviewed on Jul. 5, 2025

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
Fully refundableReserve now, pay when you stay
The price is CA $799 per night from Jul 21 to Jul 22
CA $799
CA $892 total
Jul 21 - Jul 22
includes taxes & fees
9.6/10 Exceptional! (211 reviews)
"Our recent 4 night stay at Villa di Piazzano was truly perfect in every way! Celebrating our 40th wedding anniversary could not have been more enjoyed! Having booked our stay 6 mos in advance - I communicated many times via email during that time, seeking itinerary advice from the Conceirge. I always ..."

Reviewed on Jun. 24, 2025

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 $450 per night from Jul 13 to Jul 14
CA $450
CA $508 total
Jul 13 - Jul 14
includes taxes & fees
9.8/10 Exceptional! (215 reviews)
"Amazing hotel, a must stay if visiting Cortona..best hotel in Tuscany"

Reviewed on Jul. 5, 2025

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 $534 per night from Aug 4 to Aug 5
CA $534
CA $601 total
Aug 4 - Aug 5
includes taxes & fees
9.2/10 Wonderful! (108 reviews)
"Perfect stay! Couldn’t recommend more highly"

Reviewed on Jul. 8, 2025

Il Falconiere - Relais e Chateaux
See all 1,312 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

What to do in Cortona

Cortona: 3-Hour Private Walking Tour

Cortona: 3-Hour Private Walking Tour

CA $247
per adult
Cortona: 3-Hour Private Walking Tour
Cortona Private walking Tour under the Tuscan sun

Cortona Private walking Tour under the Tuscan sun

CA $470
per adult
Cortona Private walking Tour under the Tuscan sun
Cortona

Cortona Private Guided Tour

CA $414
per traveller
Cortona Private Guided Tour
See all activities in Cortona

Frequently asked questions

How much does a Cortona vacation package cost?
You'll find cheap prices from CA $1,491 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.

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