
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
Historic Centre of Florence
Price was CA $3,022, price is now CA $1,668 per person
CA $1,668
per person
May 22 - May 27
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
7.6/10 Good! (1,006 reviews)
You have a lot of restaurants in a short walking distance. You have a famous sandwich shop you must try. Train station not too far. The hotel is very small. The staff is the best part
Reviewed on Apr 17, 2026

Hotel La Scaletta Al Ponte Vecchio
Historic Centre of Florence
Price was CA $5,057, price is now CA $3,496 per person
CA $3,496
per person
Jun 5 - Jun 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Florence (FLR)
8.8/10 Excellent! (989 reviews)
The hotel was amazing. The location was fantastic for our short city break and the staff on reception could not have been more helpful. Our room was clean and the beds were so comfortable. We got great nights sleeps as it was so quiet. Would highly recommend.
Reviewed on Apr 19, 2026

Aurum Firenze
Historic Centre of Florence
Price was CA $2,525, price is now CA $1,749 per person
CA $1,749
per person
Jul 13 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
7.6/10 Good! (1,006 reviews)
Room was clean and the ac worked well. Large opening window to the street was nice. Great location to the train station and main attractions. Breakfast was poor. Very few items. Poor quality items and kept running out. Beautiful breakfast area - could easily be the best part of stay with a little effort.
Reviewed on Apr 20, 2026

The Moon Boutique Hotel & Spa
Historic Centre of Florence
Price was CA $2,918, price is now CA $2,054 per person
CA $2,054
per person
May 31 - Jun 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9.6/10 Exceptional! (519 reviews)
Nice hotel close to the centre. Good breakfast and spa
Reviewed on Apr 18, 2026

L'Andana
Price was CA $3,783, price is now CA $2,668 per person
CA $2,668
per person
May 22 - May 27
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.4/10 Exceptional! (86 reviews)
What an amazing place I hope to get back here next year again everybody was super nice. Property was super nice. It is quite relaxing. Great food apparently a great wine as well but I don’t drink. I highly recommend anybody to go.
Reviewed on Jul 5, 2025
Cortona Hotel Deals

Villa di Piazzano - Small Luxury Hotel of the World
Localita Piazzano, C.P. 6 Cortona AR
The price is CA $992 per night from May 10 to May 11
CA $992
CA $1,104 total
May 10 - May 11
includes taxes & fees
9.8/10 Exceptional! (230 reviews)
This property is sublime. The details in the restoration, the history, the amenities all first class. The staff was amazing in making you feel comfortable and at home at the villa. Extremely peaceful.
Reviewed on Apr 19, 2026

Monastero di Cortona Hotel & Spa
Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
The price is CA $425 per night from Apr 29 to Apr 30
CA $425
CA $480 total
Apr 29 - Apr 30
includes taxes & fees
10/10 Exceptional! (266 reviews)
Staff was phenomenal!! Great team every accomplished
Reviewed on Apr 20, 2026

Il Falconiere - Relais e Chateaux
Localita San Martino 370 Cortona AR
The price is CA $652 per night from May 10 to May 11
CA $652
CA $730 total
May 10 - May 11
includes taxes & fees
9.4/10 Exceptional! (123 reviews)
Excellent staff and experiences! We had a wonderful time.
Reviewed on Nov 29, 2025
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.
What to do in Cortona

Oil museum and oil mill in Tuscany: tour and tasting
CA $32
per adult

From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
CA $193
per adult
98% of travellers recommend

Montepulciano Wine Tasting in the Tuscan Countryside
CA $41
per adult
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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.







