
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 $2,498, price is now CA $1,579 per person
CA $1,579
per person
Jul 7 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Florence (FLR)
7.6/10 Good! (1,006 reviews)
We actually booked here last minute, I read some not so nice comments but the air conditioner Works fantastic you just have to set it we kept hours on 23 I believe and it was very cool we were there from May 1st to May 10th and it was very hot on some days and we were totally comfortable, the staff is extremely helpful, breakfast was great the regular eggs and they had bacon they had fruit coffee machine was great we got cappuccinos every morning they have rolls they had a toaster it was pretty good the place is what you make it and it's right near the train station to supermarkets, it was actually a great stay and we would stay there again.
Reviewed on May 30, 2026

Aurum Uffizi
Historic Centre of Florence
Price was CA $2,505, price is now CA $1,581 per person
CA $1,581
per person
Jul 14 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Florence (FLR)
7.6/10 Good! (1,004 reviews)
Clean and long lasting hot water for shower!
Reviewed on May 30, 2026

The Moon Boutique Hotel & Spa
Historic Centre of Florence
Price was CA $2,816, price is now CA $1,847 per person
CA $1,847
per person
Jul 22 - Jul 28
found 24 hours ago
Roundtrip flight included
Montreal (YMQ) to Florence (FLR)
9.6/10 Exceptional! (544 reviews)
Excellent hotel just outside the tourist centre of Florence. The room was fantastic and the staff were extremely helpful. The breakfast was the best we had during our trip. This is the perfect home base for a Florence trip as long as you are fine with walking 10-15 minutes to get into central Florence.
Reviewed on Jun 1, 2026

Donati Luxury Tower Suites
Historic Centre of Florence
Price was CA $3,785, price is now CA $2,603 per person
CA $2,603
per person
Jul 20 - Jul 23
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.6/10 Exceptional! (63 reviews)
Agradable estancia. Excelente servicio. La habitación la mantenían siempre limpia. Todo queda cerca del área. Muy recomendable
Reviewed on May 23, 2026

Hotel La Scaletta Al Ponte Vecchio
Historic Centre of Florence
Price was CA $3,027, price is now CA $2,113 per person
CA $2,113
per person
Jul 7 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Florence (FLR)
8.8/10 Excellent! (1,000 reviews)
This place is wonderful. Perfect location close enough to the Ponte Vecchio but far enough from it that the foot traffic feels at arms length. The front desk staff is super warm and the location is beautiful. Make sure to check out the courtyard next to the front desk area and also the stunning roof top bar views. I found this spot to be exactly where I wanted to start and finish my daily walking journeys. Slip into the nearby side streets for some great cafes, restaurants and Osterias.
Reviewed on Jun 1, 2026
Cortona Hotel Deals

Villa di Piazzano - Small Luxury Hotel of the World
Localita Piazzano, C.P. 6 Cortona AR
The price is CA $972 per night from Jun 19 to Jun 20
CA $972
CA $1,082 total
Jun 19 - Jun 20
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 $516 per night from Jun 14 to Jun 15
CA $516
CA $581 total
Jun 14 - Jun 15
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 $699 per night from Jun 25 to Jun 26
CA $699
CA $781 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
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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.








