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.
Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was CA $1,870, price is now CA $1,254 per person
CA $1,254
per person
Dec 3 - Dec 8
found 24 hours ago
Roundtrip flight included
Ottawa (YOW) to Florence (FLR)
7.6/10 Good! (1,003 reviews)
El hotel es lindo y limpio… un poco pequeño pero muy céntrico nos gustó mucho … volveremos 👏🌹

Reviewed on Oct 28, 2026

Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was CA $2,402, price is now CA $1,551 per person
CA $1,551
per person
Dec 3 - Dec 8
found 24 hours ago
Roundtrip flight included
Ottawa (YOW) to Florence (FLR)
8.6/10 Excellent! (508 reviews)

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Price was CA $3,966, price is now CA $2,791 per person
CA $2,791
per person
Dec 26 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9.6/10 Exceptional! (612 reviews)
The hotel was wonderful, spotless, quiet and in a really handy location. The spa was beautiful and the breakfast was delicious with plenty of choice.

Reviewed on Oct 30, 2026

Hotel Duomo Firenze

Hotel Duomo Firenze

3 out of 5
Historic Centre of Florence
Price was CA $2,677, price is now CA $1,955 per person
CA $1,955
per person
Dec 3 - Dec 8
found 24 hours ago
Roundtrip flight included
Ottawa (YOW) to Florence (FLR)
9.2/10 Wonderful! (1,003 reviews)
This was a magical location. It was our honeymoon and the staff were overjoyed with our selection of their hotel for the occasion. They went out of their way to make our stay memorable!

Reviewed on Oct 30, 2026

Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

4 out of 5
Historic Centre of Florence
Price was CA $2,526, price is now CA $1,901 per person
CA $1,901
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Florence (FLR)
9/10 Wonderful! (1,000 reviews)

Ready to book your vacation to Cortona?

 

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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
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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 $362 per night from Nov 29 to Nov 30
CA $362
CA $405 total
Nov 29 - Nov 30
includes taxes & fees
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
Fully refundableReserve now, pay when you stay
The price is CA $511 per night from Nov 18 to Nov 19
CA $511
CA $568 total
Nov 18 - Nov 19
includes taxes & fees
Il Falconiere - Relais e Chateaux
See all 1,133 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.
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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 $189
per adult
98% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
Montepulciano Wine Tasting in the Tuscan Countryside

Montepulciano Wine Tasting in the Tuscan Countryside

CA $40
per adult
Montepulciano Wine Tasting in the Tuscan Countryside
Vino Nobile di Montepulciano winery tour and tasting

Vino Nobile di Montepulciano winery tour and tasting

CA $48
per adult
Vino Nobile di Montepulciano winery tour and tasting
See all activities in Cortona

Frequently asked questions

How much does a Cortona vacation package cost?
You'll find cheap prices from CA $1,254 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.

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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.