Cortona Vacations from $683

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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.
Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Price was $970, price is now $683 per person
$683
per person
Dec 16 - Dec 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,007 reviews)
Breakfast was excellent

Reviewed on Sep 29, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $1,049, price is now $715 per person
$715
per person
Dec 16 - Dec 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,008 reviews)
Very convenient place. It was a bit noisy at night due to being close to a popular street. Not a deal breaker for us though. Staff was super friendly. Breakfast was not so great.

Reviewed on Oct 7, 2025

Villa Cora

Villa Cora

5 out of 5
Oltrarno
Price was $2,257, price is now $1,632 per person
$1,632
per person
Dec 16 - Dec 21
found 7 hours ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
9.8/10 Exceptional! (461 reviews)
The hotel is very beautiful, and the surrounding environment is also excellent.

Reviewed on Sep 26, 2025

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Cortona Old Town
Price was $1,496, price is now $1,100 per person
$1,100
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
10/10 Exceptional! (235 reviews)
Beautiful, unique property! Stunning views of the countryside. The staff were all very helpful and friendly. We will definitely recommend!

Reviewed on Sep 27, 2025

LHP River Club

LHP River Club

5 out of 5
Santa Croce
Price was $964, price is now $720 per person
$720
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
9/10 Wonderful! (8 reviews)
Beautiful room and comfortable bed. Clean. Nice pool area. There are no elevators but the stairs are not long. AC is not very strong but suffices. Area is full of hidden gems from bakeries to late night pizza. Parking can be a challenge but not more than other parts of the city. About a 20 min walk to the center and plenty of shops and restaurants along the way.

Reviewed on Sep 23, 2025

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Discover the most popular places to visit in Cortona

Cortona featuring heritage architecture

Piazza della Repubblica

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

Cortona Cathedral is just one of the places to see in Cortona, so why not enjoy the other things to explore during your travels? Experience the area's museums and musical theater.

Cortona Cathedral

What to do in Cortona

Montepulciano Wine Tasting in the Tuscan Countryside

Montepulciano Wine Tasting in the Tuscan Countryside

$30
per adult
Montepulciano Wine Tasting in the Tuscan Countryside
3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch

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

$105
per adult
100% 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

$24
per adult
Oil museum and oil mill in Tuscany: tour and tasting
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
$620 nightly
The price is $692 total per night from Oct 20 to Oct 21
$692 total
Oct 20 - Oct 21
Total with taxes and fees
9.6/10 Exceptional! (223 reviews)
"I stayed at Villa di Piazzano for two nights and overall had a lovely experience. The check-in process was seamless, and the staff were warm, professional, and very attentive, which set a great tone from the start. The property itself is absolutely gorgeous, with beautiful grounds and a peaceful ..."

Reviewed on Sep 23, 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
$264 nightly
The price is $295 total per night from Nov 2 to Nov 3
$295 total
Nov 2 - Nov 3
Total with taxes and fees
9.8/10 Exceptional! (239 reviews)
"Beautiful, unique property! Stunning views of the countryside. The staff were all very helpful and friendly. We will definitely recommend!"

Reviewed on Sep 27, 2025

Monastero di Cortona Hotel & Spa
Hotel San Michele

Hotel San Michele

4 out of 5
Via Guelfa 15, Cortona, AR
Fully refundable
$124 nightly
The price is $146 total per night from Oct 30 to Oct 31
$146 total
Oct 30 - Oct 31
Total with taxes and fees
9/10 Wonderful! (267 reviews)
"Very friendly and helpful staff. Nice rooms"

Reviewed on Sep 7, 2025

Hotel San Michele
See all 1,290 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.

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 $683 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.

Explore a world of travel with Expedia

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.