
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.

The Moon Boutique Hotel & Spa
Historic Centre of Florence
Price was CA $3,140, price is now CA $1,856 per person
CA $1,856
per person
Oct 13 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
9.6/10 Exceptional! (462 reviews)
The hotel is located a 25 min walk away from the heart of Florence so very easy to access the main attractions within the city. The hotel itself is immaculate and the staff are extremely helpful with dealing with any questions you may have. Being able to access the spa everyday for 1 and 30 minutes is an excellent perk as the facilities are well worth a visit, you are also able to book massages for an extra fee. The breakfast also gives a variety of options to start each day and the room itself is spacious, with the shower particularly being very comfortable.
Reviewed on Aug. 13, 2025

Palazzo Firenze by Baglioni Hotels & Resorts
Historic Centre of Florence
Price was CA $10,634, price is now CA $5,709 per person
CA $5,709
per person
Oct 13 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
9.4/10 Exceptional! (230 reviews)
I VERY MUCH ENJOYED THE STAY
Reviewed on Jul. 18, 2025

Aurum Uffizi
Historic Centre of Florence
Price was CA $3,837, price is now CA $2,237 per person
CA $2,237
per person
Sep 21 - Sep 27
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Florence (FLR)
7.8/10 Good! (1,000 reviews)
Our stay was lovely, very comfortable, small but good choice of breakfast.
Beds were comfy and room was clean when we arrived and cleaned everyday.
I would only suggest maybe for a shower curtains as when we had a shower the bathroom floor would be all wet, but easily to clean. And just a note on how to use the phone if we need to call reception but overall the hotel facilities and the staff were brilliant if i could give more then 5 stars i would.
Reviewed on Aug. 19, 2025

Aurum Firenze
Historic Centre of Florence
Price was CA $3,549, price is now CA $2,129 per person
CA $2,129
per person
Sep 21 - Sep 27
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Florence (FLR)
7.6/10 Good! (1,007 reviews)
Great location. Few minutes away from train station. Not so quiet. You could hear people from outside even the windows closed. If you are staying for a few days, it’s a great location.
Reviewed on Aug. 14, 2025

Bernini Palace
Historic Centre of Florence
Price was CA $6,442, price is now CA $4,345 per person
CA $4,345
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
9.6/10 Exceptional! (1,001 reviews)
Great place and location. The staff was extremely helpful and friendly.
Reviewed on Aug. 20, 2025
Cortona Hotel Deals

Monastero di Cortona Hotel & Spa
Via del Salvatore, Cortona, AR
Fully refundableReserve now, pay when you stay
The price is CA $461 per night from Aug 24 to Aug 25
CA $461
CA $519 total
Aug 24 - Aug 25
includes taxes & fees
9.8/10 Exceptional! (230 reviews)
"Beautiful property, magical, great friendly staff, fantastic breakfast. Everything was perfect"
Reviewed on Aug. 7, 2025

Villa di Piazzano - Small Luxury Hotel of the World
Localita Piazzano, C.P. 6, Cortona, AR
Fully refundableReserve now, pay when you stay
The price is CA $808 per night from Aug 22 to Aug 23
CA $808
CA $901 total
Aug 22 - Aug 23
includes taxes & fees
9.6/10 Exceptional! (218 reviews)
"AMAZING! Gorgeous! I would recommend to everyone!"
Reviewed on Jul. 29, 2025

Il Falconiere - Relais e Chateaux
Localita San Martino 370, Cortona, AR
Fully refundableReserve now, pay when you stay
The price is CA $519 per night from Sep 1 to Sep 2
CA $519
CA $584 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (113 reviews)
"The propriety is one of the nicest I’ve stayed at. Very relaxing atmosphere, comfortable large pool area. Breakfast and lunch options are delicious. Room was very comfortable and spacious. The only problem I experienced was both adjacent rooms were smokers and did so on their patios. We couldn’t ..."
Reviewed on Aug. 14, 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 $143
per adult
100% of travellers recommend

Montepulciano: Wine Tour and tasting
CA $84
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.