Cortona Vacations from $1,049

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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.

The Latest Cortona vacation packages

Price found within the past 48 hours. Click for updated prices.
JR Hotels Hermes Firenze

JR Hotels Hermes Firenze

3 out of 5
Historic Centre of Florence
per person
Aug 14 - Aug 16
found 22 hours ago
Roundtrip flight included
Dallas (DFW) to Florence (FLR)
10/10 Exceptional! (3 reviews)
Hotel Albani Firenze

Hotel Albani Firenze

4 out of 5
Historic Centre of Florence
per person
Aug 14 - Aug 16
found 22 hours ago
Roundtrip flight included
Dallas (DFW) to Florence (FLR)
9/10 Wonderful! (1,000 reviews)
Our room was clean, quiet & close to amenities for walking to the sites of Florence. The breakfast was very good. Small hiccup with the AC the first day but the maintenance got right on it and we were cool in no time. Which was perfect in 38 degrees! Appreciated 2 luggage holders so we could be up off the floor. All the staff was helpful with organizing taxi and helping us with all our questions.

Reviewed on Jun 24, 2025

The Market Urban Hotel

The Market Urban Hotel

4 out of 5
Historic Centre of Florence
per person
Aug 14 - Aug 16
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Florence (FLR)
9.6/10 Exceptional! (1,002 reviews)
AC didn’t cool as efficiently as we would have liked. My wife and son were in the room all day and the tv kept shutting off after 10 minutes. It was unsettling.

Reviewed on Jun 24, 2025

Hotel Milu Florence

Hotel Milu Florence

4 out of 5
Historic Centre of Florence
per person
Aug 14 - Aug 16
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Florence (FLR)
9.8/10 Exceptional! (565 reviews)
Would come back in a heartbeat!

Reviewed on Jun 10, 2025

Solo Experience Hotel

Solo Experience Hotel

4 out of 5
Historic Centre of Florence
per person
Aug 14 - Aug 16
found 22 hours ago
Roundtrip flight included
Dallas (DFW) to Florence (FLR)
9.6/10 Exceptional! (779 reviews)
My family and I were so impressed with this hotel and the staff. It's a great, clean and well kept property in a wonderful location. It's a 5 minute walk to the Duomo and it is a great location for food, shopping and sightseeing. We had a suite which was spacious and clean. The hotel staff is what really makes this hotel special. Everyone who works there is so friendly, helpful and attentive to all of their guests. For example, Angela was extremely helpful and offered guests ideas on what to see in other cities. I could say something about all of the front desk staff and bellmen, but I don't have their names. Seriously, they are the best hotel staff!! I 100% recommend this hotel and My family and I would stay here again. We are picky about where we stay and we all loved it.

Reviewed on Jun 27, 2025

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Discover the most popular places to visit in Cortona

Cortona featuring heritage architecture

Piazza della Repubblica

5/5(4 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.

Piazza della Repubblica

Villa Bramasole

You can learn about the history of Cortona with a trip to Villa Bramasole. You can enjoy the wineries while in the area.

Villa Bramasole

Cortona Cathedral

Find out about the history of Cortona with a stop at Cortona Cathedral. Make time to visit the cathedral and monuments while you're in the area.

Cortona Cathedral

What to do in Cortona

For your personal cooking class in Tuscany

Amazing four courses cooking class in Tuscany

$305
per adult
Amazing four courses cooking class in Tuscany
Tuscany: Sanctuary of La Verna Day Tour Private Tour

Tuscany: Sanctuary of La Verna Day Tour Private Tour

$540
per traveler
Tuscany: Sanctuary of La Verna Day Tour Private Tour
Cortona

Cortona Private Guided Tour

$300
per traveler
Cortona Private Guided Tour
See all activities in Cortona

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
$576 nightly
The price is $643 total per night from Jul 10 to Jul 11
$643 total
Jul 10 - Jul 11
Total includes taxes and 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
$302 nightly
The price is $342 total per night from Jun 30 to Jul 1
$342 total
Jun 30 - Jul 1
Total includes taxes and fees
9.8/10 Exceptional! (212 reviews)
"Top Tier Hotel. Great amenities and service!!"

Reviewed on Jun 3, 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
Fully refundableReserve now, pay when you stay
$404 nightly
The price is $454 total per night from Jul 17 to Jul 18
$454 total
Jul 17 - Jul 18
Total includes taxes and fees
9.2/10 Wonderful! (103 reviews)
"The property was lovely. We spent time each day in their spa watching the view. The pools are great too. Sadly, it was still a bit cold to use them."

Reviewed on Jun 1, 2025

Il Falconiere - Relais e Chateaux
See all 1,308 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.

Find the Best Cortona Vacation Packages

Cortona Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Population
2,200
Max Temp Winter
45ºF
Max Temp Summer
80ºF
Top Sights
Signorelli Theatre, Cathedral of Cortona and San Luciano Winery

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Frequently asked questions

How much does a Cortona vacation package cost?
You'll find cheap prices from $1,049 on Expedia for your Cortona break. However, factors like the season, length of stay and your choice of hotel will influence how much your vacation to Cortona costs.
What are the cheapest months to go to Cortona?
October, November and December are the best times to search for cheap Cortona vacation packages. Traveling in less busy months means you can typically find lower prices on hotels and flights.
How many days is enough for Cortona?
Cortona vacations come in many shapes and sizes, but to really sink your teeth into this destination, we'd suggest 3 days is a good ballpark. In this timeframe, you can fit in headline attractions like Palazzo Comunale and Museum of the Etruscan Academy and track down some hidden gems. Don't skip neighborhoods such as Cortona Old Town and Sodo either. If you're smart with your time, you can even allow for a day trip outside of Cortona too.
Is it worth booking a vacation package to Cortona?
Whether you want to visit major attractions like Villa Bramasole and Cathedral of Cortona on your Cortona vacation, or coming for its excellent nature, views and dining, there's something for everyone here. With so much to experience, you'll soon find out why so many travelers think Cortona is a good vacation destination.
How to find the best Cortona package deals?
Start your search for a Cortona package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply a few filters, like "Property type" and "Popular locations," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Cortona package deal straight away, simply switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Cortona escape underway.
Is it cheaper to book a Cortona vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and stays individually. Better still, you can customize your Cortona trip to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Cortona?
If you're considering an impromptu Cortona vacation, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can land terrific deals on your flights and hotels by booking well in advance.
How to plan a trip to Cortona?

  1. Pick the best time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to go to Cortona.
  2. Set your budget: Factor in costs such as flights, meals and transportation when working out how much to set aside for your trip to Cortona. Then, pick a property that fits your budget, whether that's a low-cost option or a deluxe getaway.
  3. Discover Cortona with our trip planning tool: Gain insights into the most popular attractions and best properties for your trip to Cortona. You can also save your must-visit places, collaborate with your group and arrange all your plans in one place.
  4. Work out your trip length: Consider how much time you want to spend discovering Cortona. Plan your days so you can get to all the attractions and activities you're interested in at a comfortable pace.
  5. Combine your airfare and accommodations: After you've settled on your travel dates and duration, lock in the ideal Cortona vacation package for you.
  6. Book any activities or excursions: Now to the fun part --- locking in everything you want to see and do. Check out some of the exciting things to do in Cortona and reserve your tickets in advance to save time (and maybe some dollars too!).

Does Expedia offer Book Now, Pay Later Cortona vacation packages?
Your Cortona getaway should be an escape from your daily routine, not a reason for money-related stress. So to allow you a little more flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.