Title: Cortona Vacation Packages & Trips 2025/2026 from CA $1,179 | Expedia.ca [Cortona Travel Guide](https://expedia.ca/Cortona.dx601360)[Hotels in Cortona](https://expedia.ca/Cortona-Hotels.d601360.Travel-Guide-Hotels)[Vacation Rentals in Cortona](https://expedia.ca/Cortona-Vacation-Rentals.d601360.Travel-Guide-VacationRentals)[Flights to Cortona](https://expedia.ca/Cheap-Flights-To-Cortona.d601360.Travel-Guide-Flights)[Things to do in Cortona](https://expedia.ca/Things-To-Do-In-Cortona.d601360.Travel-Guide-Activities)[Cortona Car Rentals](https://expedia.ca/Car-Rentals-In-Cortona.d601360.Car-Rental-Guide) ![](https://images.trvl-media.com/place/601360/f4054673-52dd-4f97-8d57-389d1f349940.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Cortona Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place #### 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](https://www.expedia.ca/Villa-Bramasole-Cortona.d553248635931712561.Vacation-Attraction), [Piazza della Repubblica](https://www.expedia.ca/Piazza-Della-Repubblica-Cortona-Old-Town.d6102854.Vacation-Attraction) and [Cathedral of Cortona](https://www.expedia.ca/Cathedral-Of-Cortona-Cortona-Old-Town.d6102846.Vacation-Attraction) 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](https://images.trvl-media.com/lodging/29000000/28970000/28962000/28961941/26fd50f1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Aurum Firenze Historic Centre of Florence CA $1,179 per person Jan 16 - Jan 22 found 13 hours ago Roundtrip flight included Toronto (YYZ) to Florence (FLR) 7.6/10 Good! (1,004 reviews) The door to our room 108 only open halfway, the lone window facing the street doesn’t lock. The shower door doesn’t lock good, so it flooded the bathroom floor. Reviewed on Nov 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-16/2026-01-22/?FromAirport=YYZ&Destination=FLR&NumRoom=1&NumAdult=2&NumChild=0&hotelId=28961941&paandie=true&dealMarker=dIM_IvM1SHuPb2nWr8spp4NrnJfi2TgAW57gAYPhtTbA9U49N5_ctQ32UQGp5bCn) ![Aurum Uffizi](https://images.trvl-media.com/lodging/3000000/2550000/2541700/2541615/862ad26c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Aurum Uffizi Historic Centre of Florence CA $1,231 per person Jan 16 - Jan 22 found 13 hours ago Roundtrip flight included Toronto (YYZ) to Florence (FLR) 7.8/10 Good! (1,015 reviews) The room was spotless. The staff was helpful and kind. The location was great, though if you are arriving at night, the alley it is in is dark. The pillows were not at all comfortable. Reviewed on Nov 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-16/2026-01-22/?FromAirport=YYZ&Destination=FLR&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2541615&paandie=true&dealMarker=dIM_IvM1SHuPb2nWr8spp4NrnJfi2TgAW57gAYPhtTa3GpRdBb-97awA6zujKhvm) ![The Moon Boutique Hotel & Spa](https://images.trvl-media.com/lodging/23000000/22260000/22255000/22254976/205f9600_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Moon Boutique Hotel & Spa Historic Centre of Florence CA $1,422 per person Dec 8 - Dec 13 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Florence (FLR) 9.6/10 Exceptional! (485 reviews) Great hotel. Good location right across the street from the tram. Very clean and the staff is wonderful. Reviewed on Nov 1, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-08/2025-12-13/?FromAirport=YUL&Destination=FLR&NumRoom=1&NumAdult=2&NumChild=0&hotelId=22254976&paandie=true&dealMarker=FwPoV3bp4deglATcECe6lQCDeqrw-Rb-c9kE3iHCJmGguLSAGyzXWGc0EUopPbSo) ![25hours Hotel Florence Piazza San Paolino](https://images.trvl-media.com/lodging/71000000/70130000/70128100/70128094/63ed60b3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 25hours Hotel Florence Piazza San Paolino Historic Centre of Florence CA $1,551 per person Dec 8 - Dec 13 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Florence (FLR) 9.4/10 Exceptional! (895 reviews) Excellent property. Great themed rooms, good breakfast, and within walking distance of a majority of the sites. Reviewed on Nov 1, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-08/2025-12-13/?FromAirport=YUL&Destination=FLR&NumRoom=1&NumAdult=2&NumChild=0&hotelId=70128094&paandie=true&dealMarker=FwPoV3bp4deglATcECe6lWY-W2iXUDXMVYiDmxuwdk8gSZt1afmGjfuiPp2skjif) ![Il Rivalta - Place of Charme](https://images.trvl-media.com/lodging/46000000/45800000/45790300/45790281/a67d0954_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Il Rivalta - Place of Charme Historic Centre of Florence CA $1,471 per person Dec 8 - Dec 13 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Florence (FLR) 9.2/10 Wonderful! (404 reviews) The hotel is perfectly situated on the River Arno. The courtyard is lively and the roof terrace has spectacular views. It’s lovely to sit up there watching the sunset with a glass of wine. Our superior room was spacious and faced the courtyard. It was comfortable and very quiet. Breakfast is the most varied continental breakfast I’ve ever seen. We would definystay here again. Reviewed on Oct 18, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-08/2025-12-13/?FromAirport=YUL&Destination=FLR&NumRoom=1&NumAdult=2&NumChild=0&hotelId=45790281&paandie=true&dealMarker=FwPoV3bp4deglATcECe6lQCDeqrw-Rb-c9kE3iHCJmHq4Yc6q4R2OIMspHNO6j8Q) ## Ready to book your vacation to Cortona? Choose your dates ## Cortona Hotel Deals ![Monastero di Cortona Hotel & Spa](https://images.trvl-media.com/lodging/24000000/23270000/23264500/23264410/cea3a0e9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Monastero di Cortona Hotel & Spa Via del Salvatore, Cortona, AR Fully refundableReserve now, pay when you stay CA $388 CA $434 total Nov 11 - Nov 12 includes taxes & fees 9.8/10 Exceptional! (248 reviews) Wow best experience, fantastic service, awesome staff, beautiful room and cortona is very impressive Reviewed on Oct 29, 2025 [](https://expedia.ca/Hotel-Search?startDate=11%2F11%2F2025&endDate=12%2F11%2F2025&selected=23264410&PinnedHotelID=23264410&HadPinnedHotel=true®ionId=601360) ![Villa di Piazzano - Small Luxury Hotel of the World](https://images.trvl-media.com/lodging/1000000/980000/972000/971985/473f66a9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Villa di Piazzano - Small Luxury Hotel of the World Localita Piazzano, C.P. 6, Cortona, AR 9.8/10 Exceptional! (227 reviews) This is a classic luxury hotel. I can't imagine the amount of time and energy it takes to upkeep this property. But they somehow manage to maintain a spotless, manicured and warm environment. The room was quite large and rich in design. The restaurant and the staff who work there are excellent. I ... Reviewed on Oct 9, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=17%2F11%2F2025&endDate=18%2F11%2F2025&selected=971985&PinnedHotelID=971985&HadPinnedHotel=true®ionId=601360) [](https://expedia.ca/Hotel-Search?startDate=17%2F11%2F2025&endDate=18%2F11%2F2025&selected=971985&PinnedHotelID=971985&HadPinnedHotel=true®ionId=601360) ![Hotel San Michele](https://images.trvl-media.com/lodging/1000000/990000/984500/984435/cd5b1ca8_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel San Michele Via Guelfa 15, Cortona, AR 9/10 Wonderful! (268 reviews) Very friendly and helpful staff. Nice rooms Reviewed on Sep 7, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=17%2F11%2F2025&endDate=18%2F11%2F2025&selected=984435&PinnedHotelID=984435&HadPinnedHotel=true®ionId=601360) [](https://expedia.ca/Hotel-Search?startDate=17%2F11%2F2025&endDate=18%2F11%2F2025&selected=984435&PinnedHotelID=984435&HadPinnedHotel=true®ionId=601360) [See all 1,286 properties in Cortona](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=04%2F11%2F2025&endDate=05%2F11%2F2025®ionId=601360) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### What to do in Cortona ![3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch](https://mediaim.expedia.com/localexpert/47282553/e14b5a73-0ff4-428f-a567-234540a94e59.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch CA $144 per adult **100%** of travellers recommend [](https://expedia.ca/things-to-do/from-rome-bagnoregio-orvieto-day-trip-with-tuscany-wine-tasting-lunch.a47282553.activity-details) ![Oil museum and oil mill in Tuscany: tour and tasting](https://mediaim.expedia.com/localexpert/47137603/cba72fc6-87d4-4e36-971f-bc6dc0d28c6e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Oil museum and oil mill in Tuscany: tour and tasting CA $32 per adult [](https://expedia.ca/things-to-do/oil-museum-and-oil-mill-in-tuscany-tour-and-tasting.a47137603.activity-details) ![Montepulciano Wine Tasting in the Tuscan Countryside](https://mediaim.expedia.com/localexpert/50286653/77c79a76-70f1-4375-9739-0f0f71d7da02.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Montepulciano Wine Tasting in the Tuscan Countryside CA $40 per adult [](https://expedia.ca/things-to-do/montepulciano-wine-tasting-in-the-tuscan-countryside.a50286653.activity-details) [See all activities in Cortona](https://expedia.ca/things-to-do/search?rid=601360) ## Explore a world of travel with Expedia - 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[Crete Senesi Vacations](https://www.expedia.ca/Crete-Senesi.d6342453.Destination-Travel-Guides) - [Visit Creti](https://www.expedia.ca/Creti.dx3000439377) - [Croce del Pratomagno](https://www.expedia.ca/Croce-Del-Pratomagno-Loro-Ciuffenna.d553248621562145026.Vacation-Attraction) - [Fortress of Montalcino](https://www.expedia.ca/Fortress-Of-Montalcino-Montalcino.d553248621533000896.Vacation-Attraction) - [Le Miccine](https://www.expedia.ca/Le-Miccine-Cavriglia.d553248621532500723.Vacation-Attraction) - [Visit Marciano della Chiana](https://www.expedia.ca/Marciano-Della-Chiana.dx6285674) - [Visit Mercatale di Cortona](https://www.expedia.ca/Mercatale-Di-Cortona.dx601101) - [Visit Metelliano](https://www.expedia.ca/Metelliano.dx553248635975868789) - [Visit Montagnano](https://www.expedia.ca/Montagnano.dx6361223) - [Montalcino Vacations](https://www.expedia.ca/Montalcino.d6025631.Destination-Travel-Guides) - [Visit Montepulciano Stazione](https://www.expedia.ca/Montepulciano-Stazione.dx6285775) - [Montepulciano Vacations](https://www.expedia.ca/Montepulciano.d601351.Destination-Travel-Guides) - [Murlo Vacations](https://www.expedia.ca/Murlo.d6046740.Destination-Travel-Guides) - [Visit Ossaia](https://www.expedia.ca/Ossaia.dx6361235) - [Palazzo Ricci](https://www.expedia.ca/Palazzo-Ricci-Montepulciano.d553248621532500182.Vacation-Attraction) - [Piazza Grande](https://www.expedia.ca/Piazza-Grande-Quartiere-di-Porta-Crucifera.d6104294.Vacation-Attraction) - [Pienza Cathedral](https://www.expedia.ca/Pienza-Cathedral-Pienza.d6105122.Vacation-Attraction) - [Pienza Vacations](https://www.expedia.ca/Pienza.d6023645.Destination-Travel-Guides) - [Piscine Termali Theia](https://www.expedia.ca/Piscine-Termali-Theia-Chianciano-Terme.d553248621555471462.Vacation-Attraction) - [Visit Portole](https://www.expedia.ca/Portole.dx3000390328) - [Visit Potassa](https://www.expedia.ca/Potassa.dx6361322) - [Visit Rigutino](https://www.expedia.ca/Rigutino.dx6361226) - [San Donato Hospital](https://www.expedia.ca/San-Donato-Hospital-Arezzo.d553248621583444251.Vacation-Attraction) - [Visit San Pietro a Cegliolo](https://www.expedia.ca/San-Pietro-A-Cegliolo.dx6130155) - [Visit Sinalunga](https://www.expedia.ca/Sinalunga.dx603293) - [Visit Tegoleto](https://www.expedia.ca/Tegoleto.dx3000708346) - [Tenuta Greppo Franco Biondi Santi](https://www.expedia.ca/Tenuta-Greppo-Franco-Biondi-Santi-Montalcino.d6103260.Vacation-Attraction) - [Tenuta Valdipiatta](https://www.expedia.ca/Tenuta-Valdipiatta-Montepulciano.d6105004.Vacation-Attraction) - [Terme di Montepulciano Spa](https://www.expedia.ca/Terme-Di-Montepulciano-Spa-Montepulciano.d6169786.Vacation-Attraction) - [Visit Terontola](https://www.expedia.ca/Terontola.dx6025579) - [Val d'Orcia Vacations](https://www.expedia.ca/Val-DOrcia.d6047918.Destination-Travel-Guides) ### Cars - [Car rental Castiglion Fiorentino](https://www.expedia.ca/Car-Rentals-In-Castiglion-Fiorentino.d6047858.Car-Rental-Guide) - [Car rentals near Cortona Old Town](https://www.expedia.ca/Car-Rentals-In-Cortona-Old-Town.d553248633938945259.Car-Rental-Guide) - [Car rental Mercatale di Cortona](https://www.expedia.ca/Car-Rentals-In-Mercatale-Di-Cortona.d601101.Car-Rental-Guide) - [Car rental Montepulciano Stazione](https://www.expedia.ca/Car-Rentals-In-Montepulciano-Stazione.d6285775.Car-Rental-Guide) - [Car rental Terontola](https://www.expedia.ca/Car-Rentals-In-Terontola.d6025579.Car-Rental-Guide) - [Car rental Torrita di Siena](https://www.expedia.ca/Car-Rentals-In-Torrita-Di-Siena.d6046345.Car-Rental-Guide) ### Other - [Things to do in Brolio](https://www.expedia.ca/Things-To-Do-In-Brolio.d6361222.Travel-Guide-Activities) - [Things to do in Lucignano](https://www.expedia.ca/Things-To-Do-In-Lucignano.d6048408.Travel-Guide-Activities) - [Things to do in Sinalunga](https://www.expedia.ca/Things-To-Do-In-Sinalunga.d603293.Travel-Guide-Activities) - [Things to do in Terontola](https://www.expedia.ca/Things-To-Do-In-Terontola.d6025579.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. 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Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)