Name: Hotel San Michele
Price range: CA $173
Rating: 9

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.

Boccioleto Resort&Spa

CA $1,663

per person

Jul 5 - Jul 10

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Florence (FLR)

9.2/10 Wonderful! (119 reviews)

Staff were very friendly and the rooms were clean and spacious!

Reviewed on Nov 17, 2025

Aurum Uffizi

Historic Centre of Florence

CA $1,695

per person

Jul 13 - Jul 18

found 15 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Florence (FLR)

7.6/10 Good! (1,011 reviews)

Excellent hotel and staff customer service

Reviewed on May 20, 2026

Aurum Firenze

Historic Centre of Florence

CA $1,689

per person

Jul 13 - Jul 18

found 15 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Florence (FLR)

7.6/10 Good! (1,012 reviews)

The evening adter 10pm manager on duty was very helpful!!! He was able to assist and provide everything we needed. Sorry, I don't remember his name. Thank you!

Reviewed on May 19, 2026

The Moon Boutique Hotel & Spa

Historic Centre of Florence

CA $2,223

per person

Jul 13 - Jul 18

found 15 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Florence (FLR)

9.6/10 Exceptional! (539 reviews)

Great staff, clean rooms and all good on everything.

Reviewed on May 17, 2026

LHP River Club

Santa Croce

CA $1,757

per person

Jul 5 - Jul 10

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Florence (FLR)

9.4/10 Exceptional! (27 reviews)

Amazing hotel and amazing staff. We had the standard loft with a hot tub inside our bedroom! Loved it. Even though the reception is only open 9am-5pm, the hotel staff were very good at communicating with us through WhatsApp even when outside of these hours. The hotel feels very private. Love love love.

Reviewed on Apr 17, 2026

Ready to book your vacation to Cortona?

Choose your dates

Cortona Hotel Deals

Villa di Piazzano - Small Luxury Hotel of the World

Localita Piazzano, C.P. 6 Cortona AR

CA $871

CA $971 total

May 28 - May 29

includes taxes & fees

9.8/10 Exceptional! (235 reviews)

"The Hotel and grounds are beautiful and immaculately maintained. The entire staff really stands out. So friendly and welcoming. Those little gestures of respect and kindness are appreciated. Also it’s very convenient that they can speak English. There are several beautiful hotels in the area to experience, ..."

Reviewed on May 14, 2026

Monastero di Cortona Hotel & Spa

Via del Salvatore Cortona AR

Fully refundableReserve now, pay when you stay

CA $465

CA $524 total

May 31 - Jun 1

includes taxes & fees

10/10 Exceptional! (277 reviews)

"All aspects of service are superlative! The spa, restaurants and bar are excellent. The location in Cortona is very nice. Historic features of the hotel are impressive, as is the restoration."

Reviewed on May 20, 2026

Hotel San Michele

Via Guelfa 15 Cortona AR

Fully refundableReserve now, pay when you stay

CA $173

CA $204 total

Jun 7 - Jun 8

includes taxes & fees

9/10 Wonderful! (276 reviews)

"Great and helpful staff. Room was great"

Reviewed on Apr 28, 2026

See all 1,178 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.