Name: Hotel San Michele
Price range: CA $192

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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.

Eurostars Florence Boutique

Historic Centre of Florence

CA $1,938

per person

May 23 - May 28

found 21 hours 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

Relais Uffizi, Tailor made Hotel

Historic Centre of Florence

CA $3,027

per person

May 19 - May 24

found 1 day ago

Roundtrip flight included

Montreal (YUL) to Florence (FLR)

9.4/10 Exceptional! (127 reviews)

The room was stunning, it was large, the bed was comfy and the design was unique. Staff were very friendly and helpful.

Reviewed on Feb 26, 2026

Hotel La Scaletta Al Ponte Vecchio

Historic Centre of Florence

CA $2,334

per person

May 17 - May 23

found 1 day ago

Roundtrip flight included

Montreal (YMQ) to Florence (FLR)

8.8/10 Excellent! (967 reviews)

Fantastic location for everything whilst not being in the middle of it all. The staff were all lovely and everything super clean. Only issue was the aircon didn't work and we couldn’t open the windows due to mosquitoes (discovered this after the first night with it open - didn’t make that mistake again!). It’s quite an unusual interior with a tiny lift and lots of stairs so just be aware of that - it didn’t bother us though, we loved the charm.

Reviewed on Mar 12, 2026

Il Rivalta - Place of Charme

Historic Centre of Florence

CA $2,875

per person

May 17 - May 23

found 1 day ago

Roundtrip flight included

Montreal (YMQ) to Florence (FLR)

9.2/10 Wonderful! (472 reviews)

This was probably the best hotel I have ever stayed in. It felt so luxurious, clean, and beautiful. You can tell they really take pride in the property. The breakfast was delicious and the staff was top notch!

Reviewed on Mar 13, 2026

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Cortona Hotel Deals

Villa di Piazzano - Small Luxury Hotel of the World

Localita Piazzano, C.P. 6 Cortona AR

CA $934

CA $1,034 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 $383

CA $428 total

Mar 29 - Mar 30

includes taxes & fees

Hotel San Michele

Via Guelfa 15 Cortona AR

CA $192

CA $217 total

Mar 27 - Mar 28

includes taxes & fees

See all 1,170 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.