
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.

c-hotels Club
Historic Centre of Florence
Price was CA $2,411, price is now CA $1,751 per person
CA $1,751
per person
May 16 - May 22
found 20 hours ago
Roundtrip flight included
Toronto (YYZ) to Florence (FLR)
8.4/10 Very Good! (1,001 reviews)
I love this hotel and the staff. They are so helpful. They even help me retrieve my delayed baggage from the airport. It’s walkable to all the sightseeing and the tours plus it’s right by the train station.
Reviewed on Nov 28, 2025

Grand Hotel Cavour
Historic Centre of Florence
Price was CA $3,877, price is now CA $2,614 per person
CA $2,614
per person
May 30 - Jun 5
found 14 hours ago
Roundtrip flight included
Montreal (YUL) to Florence (FLR)
9.2/10 Wonderful! (1,000 reviews)
Great hotel near the center. Walking distance to everything. I enjoyed the quality of the hotel and the roof top bar was amazing. Good service. Rooms were a little small but not sure if that was because of my budget or whether the hotel rooms were just smaller due to the type/age of the building. All in all I would recommend and most of your time is spent outdoors anyway.
Reviewed on Mar 3, 2026

The Moon Boutique Hotel & Spa
Historic Centre of Florence
Price was CA $3,164, price is now CA $2,158 per person
CA $2,158
per person
May 30 - Jun 5
found 14 hours ago
Roundtrip flight included
Montreal (YUL) to Florence (FLR)
9.6/10 Exceptional! (511 reviews)
Outstanding Boutique Hotel. Friendly Multilingual Staff, Great Breakfast, beautiful and spacious room. Absolutely amazing Wellness Spa! Centrally located for easy access to all of Firenze via public transportation. 30 mins from airport. I highly recommend The Moon Hotel And Spa!
Reviewed on Feb 23, 2026

Hotel Berchielli
Historic Centre of Florence
Price was CA $4,320, price is now CA $3,071 per person
CA $3,071
per person
May 21 - May 27
found 10 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Florence (FLR)
9.4/10 Exceptional! (1,001 reviews)
Very good Breakfast with many food options. Great service !
Reviewed on Jan 21, 2026

Villa Tolomei Hotel & Resort
Oltrarno
Price was CA $2,894, price is now CA $2,094 per person
CA $2,094
per person
May 21 - May 27
found 10 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Florence (FLR)
8.8/10 Excellent! (403 reviews)
Staff is wonderful and kind, very accommodating. We stayed here with a lot of family members for our wedding, we got a beautiful spacious suite with the best courtyard views. The rooms are so beautifully designed, the whole villa is just dreamy and true Tuscany. Breakfast is amazing with so many options and so fresh, so delicious! Service is great too. Overall cannot beat the location. We also held our wedding reception dinner here and the food and service and spaces we used were amazing. They even gave us complimentary bottle of champagne and homemade cookies in our room with a lovely note. Overall, we hope to be back!
Reviewed on Nov 25, 2025
Cortona Hotel Deals

Villa di Piazzano - Small Luxury Hotel of the World
Localita Piazzano, C.P. 6 Cortona AR
The price is CA $929 per night from Apr 9 to Apr 10
CA $929
CA $1,035 total
Apr 9 - Apr 10
includes taxes & fees
9.8/10 Exceptional! (228 reviews)
Room was wonderful, bathroom spacious and well appointed. Staff amazing and so friendly
Reviewed on Nov 6, 2025

Monastero di Cortona Hotel & Spa
Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
The price is CA $386 per night from Mar 15 to Mar 16
CA $386
CA $431 total
Mar 15 - Mar 16
includes taxes & fees

Hotel San Michele
Via Guelfa 15 Cortona AR
The price is CA $172 per night from Mar 27 to Mar 28
CA $172
CA $195 total
Mar 27 - Mar 28
includes taxes & fees
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 $127
per adult
100% of travellers recommend

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

Montepulciano Wine Tasting in the Tuscan Countryside
CA $40
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.








