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.

Hotel La Scaletta Al Ponte Vecchio

Historic Centre of Florence

CA $1,841

per person

May 17 - May 21

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Florence (FLR)

8.8/10 Excellent! (965 reviews)

The staff at breakfast prepare plain scrambled eggs for our 7 month old son and were very sweet! This our second time staying here and we absolutely love the hotel. Location, views, comfort. 10/10!

Reviewed on Feb 28, 2026

Eurostars Florence Boutique

Historic Centre of Florence

CA $1,960

per person

Apr 20 - Apr 26

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Florence (FLR)

8.6/10 Excellent! (483 reviews)

The room was clean and the staff very accommodating. The breakfast was quite sufficient and had a good variety. The location is great. It's a short walk from the square, shopping and from restaurants.

Reviewed on Dec 13, 2025

Hotel Alessandra

Historic Centre of Florence

CA $1,959

per person

May 20 - May 26

found 4 hours ago

Roundtrip flight included

Montreal (YUL) to Florence (FLR)

9.2/10 Wonderful! (849 reviews)

Clean room, amazing staff, location is great

Reviewed on Feb 2, 2026

Il Rivalta - Place of Charme

Historic Centre of Florence

CA $2,801

per person

May 17 - May 23

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Florence (FLR)

9.2/10 Wonderful! (472 reviews)

Staff was extremely attentive

Reviewed on Mar 4, 2026

Hotel Santa Maria Novella

Historic Centre of Florence

CA $3,394

per person

May 18 - May 24

found 17 hours ago

Roundtrip flight included

Montreal (YUL) to Florence (FLR)

9.6/10 Exceptional! (1,000 reviews)

Absolute perfection!!

Reviewed on Mar 3, 2026

Ready to book your vacation to Cortona?

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Cortona Hotel Deals

Villa di Piazzano - Small Luxury Hotel of the World

Localita Piazzano, C.P. 6 Cortona AR

CA $947

CA $1,048 total

Mar 28 - Mar 29

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

CA $388

CA $433 total

Mar 15 - Mar 16

includes taxes & fees

Hotel San Michele

Via Guelfa 15 Cortona AR

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See all 1,168 properties in Cortona

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.