
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 Firenze
Historic Centre of Florence
Price was CA $2,048, price is now CA $1,443 per person
CA $1,443
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
7.6/10 Good! (1,006 reviews)
Great location, lots restaurants shops nearby. Easy to access centre. Room modern reasonably clean but very small. Shower like a postage stamp.
Reviewed on Jun 3, 2026

SPLENDIDE RIVIERA
Price was CA $3,399, price is now CA $2,342 per person
CA $2,342
per person
Jul 20 - Jul 26
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Pisa (PSA)
9.8/10 Exceptional! (16 reviews)
The property was very nice, very clean and well maintained. The staff was amazing and always ready to help. Breakfast was great as well!We will definitely return here next year!
Reviewed on May 28, 2026

The James Suite Hotel Firenze 1564 - Small Luxury Hotels of the World
Historic Centre of Florence
Price was CA $4,347, price is now CA $3,148 per person
CA $3,148
per person
Jul 26 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
10/10 Exceptional! (18 reviews)
Outstanding hotel and a remarkable experience staying there. The room was large and beautifully decorated as the rest of the hotel. Service was impeccable and friendly. Food was great. Lovely and intimate atmosphere. Attention to details and distinctive effort to attend to our needs. The hotel manager and Lavinia at the front desk stood out, but everybody else was extremely helpful. I hope to return!
Reviewed on Nov 14, 2025

Hotel degli Orafi
Historic Centre of Florence
Price was CA $2,712, price is now CA $1,983 per person
CA $1,983
per person
Aug 23 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
9.6/10 Exceptional! (1,002 reviews)
Room was clean and cool.
Beds very hard though
Staff at front desk were helpful
Great location for walking to shops restaurants and local sites
Reviewed on May 29, 2026

Dimora Palanca Boutique & SPA
Historic Centre of Florence
Price was CA $2,711, price is now CA $1,993 per person
CA $1,993
per person
Aug 12 - Aug 18
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.2/10 Wonderful! (65 reviews)
I particularly love the authenticity of the building being hundreds of hundreds of years old and yet well cut, beautiful staff beautiful spa only lacking in the dining aspect but everything else was perfect. Highly recommend but recommend going out for dinner.
Reviewed on Nov 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 $971 per night from Jul 1 to Jul 2
CA $971
CA $1,081 total
Jul 1 - Jul 2
includes taxes & fees
9.8/10 Exceptional! (235 reviews)
"The Hotel and grounds are beautiful and immaculately maintained. The entire staff really stands out. So friendly and welcoming. Those little gestures of respect and kindness are appreciated. Also it’s very convenient that they can speak English. There are several beautiful hotels in the area to experience, ..."
Reviewed on May 14, 2026

Monastero di Cortona Hotel & Spa
Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
The price is CA $563 per night from Jun 18 to Jun 19
CA $563
CA $633 total
Jun 18 - Jun 19
includes taxes & fees
10/10 Exceptional! (283 reviews)
"Beautiful property - great location. Staff was wonderful. They organized transportation for us and the driver was fantastic - ask for Tony!"
Reviewed on May 31, 2026

Il Falconiere - Relais e Chateaux
Localita San Martino 370 Cortona AR
The price is CA $616 per night from Jun 25 to Jun 26
CA $616
CA $691 total
Jun 25 - Jun 26
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

From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
CA $176
per adult
98% of travellers recommend

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

Tasting Tour in One of The Most Beautiful Cellars in the World
CA $53
per adult
100% of travellers recommend
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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.







