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
Santa Croce
Save 100% on your flight
per person
Jun. 6 - Jun. 11
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
7.8/10 Good! (1,006 reviews)
The water gets cold fast

Reviewed on Mar. 23, 2025

Grand Hotel Cavour

Grand Hotel Cavour

4 out of 5
Duomo
Save 100% on your flight
per person
Jun. 6 - Jun. 11
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9.2/10 Wonderful! (1,005 reviews)
Convenient area, beautiful lobby and friendly staff. The room was awful with a scary hole on the sealing and the shower hook was broken so I had to use the little hose. Proper maintenance is long fue and it shows once you enter the room.

Reviewed on Mar. 25, 2025

Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

3 out of 5
Oltrarno
per person
Jun. 6 - Jun. 11
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
8.8/10 Excellent! (819 reviews)
Front desk people are very helpful

Reviewed on Mar. 22, 2025

Villa Neroli

Villa Neroli

4 out of 5
Coverciano
per person
Jun. 10 - Jun. 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Florence (FLR)
9.6/10 Exceptional! (355 reviews)
Super friendly staffs, super nice room

Reviewed on Feb. 14, 2025

Palazzo Firenze by Baglioni Hotels & Resorts

Palazzo Firenze by Baglioni Hotels & Resorts

5 out of 5
Santa Croce
Save 100% on your flight
per person
May 6 - May 10
found 20 hours ago
Roundtrip flight included
Montreal (YUL) to Florence (FLR)
9.4/10 Exceptional! (223 reviews)
During our recent visit to Florence, we had the pleasure of staying at Palazzo Firenze, and it was absolutely perfect. The staff provided exceptional service and had great knowledge of the area. Our room was spotless and incredibly comfortable. The hotel's location was ideal for sightseeing and dining. We couldn’t have chosen a better place to stay and would definitely return.

Reviewed on Feb. 18, 2025

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
Fully refundableReserve now, pay when you stay
The price is CA $647 per night from Apr. 1 to Apr. 2
CA $647
CA $724 total
includes taxes & fees
Apr 1 - Apr 2
9.6/10 Exceptional! (200 reviews)
"The Villa di Piazzano is stunning down to the smallest detail. The staff is attentive, pleasant and helpful. The food and wine at the onsite restaurant was some of the best we had on our 23-day trip across Italy. One of our favorite stays for sure!"

Reviewed on Oct. 29, 2024

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 $448 per night from Apr. 6 to Apr. 7
CA $448
CA $505 total
includes taxes & fees
Apr 6 - Apr 7
9.8/10 Exceptional! (204 reviews)
Good
"Super friendly service from most of the staff and beautiful property, restaurant and bars were great too."

Reviewed on Dec. 2, 2024

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 $516 per night from Apr. 9 to Apr. 10
CA $516
CA $580 total
includes taxes & fees
Apr 9 - Apr 10
9.2/10 Wonderful! (96 reviews)
"Stunning property with an amazing restaurant."

Reviewed on Dec. 12, 2024

Il Falconiere - Relais e Chateaux
See all 1,280 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

Frequently asked questions

How much does a Cortona vacation package cost?
You’ll find cheap prices from CA $1,786 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?
If you’d like to snag a cheap Cortona vacation package, consider traveling in December, January and February. You’re likely to find better prices on airfares and hotels during these months — perfect for travelers wishing to save money.
How many days is enough for Cortona?
With around 3 days, you’ll have enough time to enjoy popular neighborhoods like Cortona Old Town and Sodo during your Cortona vacation. Be sure to also add Palazzo Comunale and Museum of the Etruscan Academy to your must-see list. Searching for more adventures? Consider exploring outside of Cortona on tours and day trips.
Is it worth booking a vacation package to Cortona?
Popular for its views, dining and walking trails, a Cortona vacation is a hit with all kinds of visitors. Be sure to check out top sights like Villa Bramasole and Piazza della Repubblica, and consider renting a set of wheels for day trips to discover even more.
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. Choose when to go: Check your calendar and get packing. Your favorite season and the type of activities available will also help you decide when to escape to Cortona.
  2. Budget wisely: Besides the price of your stay, you’ll need to factor in other expenses too. These include food, transportation and flights. Also, set aside some extra funds for unexpected costs that could crop up during your trip to Cortona.
  3. Work out your trip length: Think about how much time you’d like to spend discovering Cortona. Plan your itinerary so you can get to all the attractions and experiences you’re interested in at a leisurely pace.
  4. Bundle your accommodations and airfare: Once you’ve nailed down your dates and duration, book the right Cortona vacation package for you.

What to do in Cortona

Cortona

Cortona Private Guided Tour

CA $406
per traveller
Cortona Private Guided Tour
Tuscany: Sanctuary of La Verna Day Tour Private Tour

Tuscany: Sanctuary of La Verna Day Tour Private Tour

CA $732
per traveller
Tuscany: Sanctuary of La Verna Day Tour Private Tour
3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch

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

CA $178
per adult
100% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
See all activities in Cortona
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.