Name: Hotel San Michele
Price range: CA $165

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

CA $1,571

per person

May 24 - May 30

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Florence (FLR)

7.6/10 Good! (1,006 reviews)

Breakfast was ok but we found it difficult to get healthy food. There seemed to be a finite amount of fruit and yogurt (managed to get a yogurt one morning out of four). That said we opted for 8 am breakfast and might have had more luck earlier. Hotel was well located and felt really secure. I would stay there again.

Reviewed on Apr 13, 2026

Precise Tale Poggio Alla Sala

CA $2,657

per person

May 29 - Jun 1

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Florence (FLR)

9.4/10 Exceptional! (124 reviews)

Absolutely an amazing stay. Very charming and well kept. Essentially a resort with a palatial feel. Loved walking the grounds and relaxing. Excellent restaurant, breakfast was included. The setting is quiet and beautiful. Will book again.

Reviewed on Apr 13, 2026

EXE Toscana

Lucca Historical Center

CA $2,492

per person

May 19 - May 25

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Florence (FLR)

8.4/10 Very Good! (822 reviews)

Room was run down and the breakfast was included in the past but not now. Staff said that the name change and rebranding was meant to attract business people but there were no working outlets in the room and no usb or other charging outlets apart from one socket in the bathroom. Very inconvenient. The place was much nicer to stay at in the past 15 years but has been let down by its owners sadly.

Reviewed on Apr 14, 2026

The Moon Boutique Hotel & Spa

Historic Centre of Florence

CA $2,287

per person

Jun 9 - Jun 13

found 12 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Florence (FLR)

9.6/10 Exceptional! (515 reviews)

Five STAR! Amazing Hotel! Spa Perfecto! Lovely Stay!

Reviewed on Apr 16, 2026

c-hotels Joy

Historic Centre of Florence

CA $2,228

per person

May 24 - May 30

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Florence (FLR)

9/10 Wonderful! (1,000 reviews)

Well located for the main train station and about a 15 minute walk to the Duomo. Friendly staff at all times. Comfortable room. Breakfast was free and okay.

Reviewed on Apr 4, 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 $994

CA $1,106 total

May 10 - May 11

includes taxes & fees

9.8/10 Exceptional! (229 reviews)

We really enjoyed the hotel, very clean, good atmosphere!!!

Reviewed on Apr 10, 2026

Monastero di Cortona Hotel & Spa

Via del Salvatore Cortona AR

Fully refundableReserve now, pay when you stay

CA $386

CA $437 total

Apr 26 - Apr 27

includes taxes & fees

10/10 Exceptional! (263 reviews)

I did not drive to or from the hotel.

Reviewed on Apr 8, 2026

Hotel San Michele

Via Guelfa 15 Cortona AR

Fully refundableReserve now, pay when you stay

CA $165

CA $194 total

Apr 20 - Apr 21

includes taxes & fees

See all 1,175 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.