A hillside town with historic buildings, a church, and vineyards.

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.
  • Jan 10 - Jan 16

    Art Hotel Villa Agape - Place of Charme + Flight

    Oltrarno
    5 nights
    4.0 star property
    9.8/10 - Exceptional (1,002 reviews)
    Roundtrip • Montreal (YUL) - Florence (FLR)
    YUL - FCO • Nonstop FCO - YUL • 1 stop
    CA $1,656
    CA $1,395
    per traveller
    found 1 day ago
    Art Hotel Villa Agape - Place of Charme
  • Dec 28 - Jan 3

    Villa Tolomei Hotel & Resort + Flight

    Oltrarno
    5 nights
    5.0 star property
    8.8/10 - Excellent (449 reviews)
    "The property was lovely. A former 15th(?) century monastery located on a hilltop overlooking parts of Florence. Surrounded by olive and fruit trees, and gardens. It's past the Roman gate, about a 30 euro cab ride from the center of town. Though they didn't tell us until we asked, there's a shuttle that will take you down the hill to the Roman Gate where taxis and busses can be found. We arrived just after the hotel restaurant had closed for the afternoon by a minute. They were kind/professional..."
    Reviewed November 6, 2026
    Roundtrip • Toronto (YYZ) - Florence (FLR)
    YYZ - FCO • 2 stops FCO - YYZ • 1 stop
    CA $3,248
    CA $2,492
    per traveller
    found 1 day ago
    Villa Tolomei Hotel & Resort
  • Jan 10 - Jan 16

    Bernini Palace + Flight

    Historic Centre of Florence
    5 nights
    5.0 star property
    9.8/10 - Exceptional (1,004 reviews)
    Roundtrip • Montreal (YUL) - Florence (FLR)
    YUL - FCO • Nonstop FCO - YUL • 1 stop
    CA $2,145
    CA $1,655
    per traveller
    found 1 day ago
    Bernini Palace
  • Dec 28 - Jan 3

    The Hoxton, Florence + Flight

    Historic Centre of Florence
    5 nights
    4.0 star property
    9.4/10 - Exceptional (385 reviews)
    "Nice quiet location with well appointed rooms."
    Reviewed November 7, 2026
    Roundtrip • Toronto (YYZ) - Florence (FLR)
    YYZ - FCO • 2 stops FCO - YYZ • 1 stop
    CA $2,882
    CA $2,308
    per traveller
    found 1 day ago
    The Hoxton, Florence
  • Jan 10 - Jan 16

    Hotel Calimala Florence + Flight

    Historic Centre of Florence
    5 nights
    4.0 star property
    9.6/10 - Exceptional (1,002 reviews)
    "Great hotel, good location, staff was great, would recommend."
    Reviewed November 7, 2026
    Roundtrip • Montreal (YUL) - Florence (FLR)
    YUL - FCO • Nonstop FCO - YUL • 1 stop
    CA $2,034
    CA $1,652
    per traveller
    found 1 day ago
    Hotel Calimala Florence

Where to stay in Cortona

Find the best Cortona areas and neighborhoods for the activities you enjoy most. Learn more about Cortona
Learn more about Cortona

Cortona Old Town

Cortona Old Town is noteworthy for its historic sites, and you can make a stop at top attractions like Piazza della Repubblica and Giuseppe Garibaldi Memorial.

Discover the most popular places to visit in Cortona

What to do in Cortona

Cortona Hotel Deals

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.

Frequently Asked Questions

How much does a Cortona vacation package cost?

You'll find cheap prices from CA $1,395 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.