Title: Cortona Vacation Packages & Trips 2025/2026 from CA $1,599 | 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. ![Anglo American Hotel Florence, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/30000/22700/22650/76ebcb30_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Anglo American Hotel Florence, Curio Collection by Hilton Historic Centre of Florence CA $1,599 per person Jan 12 - Jan 18 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Florence (FLR) 8.4/10 Very Good! (805 reviews) Room was clean and staff were nice. The only thing that bothered us were the mosquitoes inside the room. We got a lot of bites. Reviewed on Nov 4, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-12/2026-01-18/?FromAirport=YUL&Destination=FLR&NumRoom=1&NumAdult=2&NumChild=0&hotelId=22650&paandie=true&dealMarker=uFYi4Web8E_xB1SizqkjRQ8YgqBPBQ_aadSO3MvVWIU5Sne4JjyQWI9LHo2h_gBw) ![Villa Cora](https://images.trvl-media.com/lodging/1000000/30000/22600/22579/bc8037ee_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Villa Cora Oltrarno CA $3,234 per person Jan 5 - Jan 11 found 19 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Florence (FLR) 9.8/10 Exceptional! (467 reviews) Nice property and staff. Reviewed on Nov 13, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-05/2026-01-11/?FromAirport=YYZ&Destination=FLR&NumRoom=1&NumAdult=2&NumChild=0&hotelId=22579&paandie=true&dealMarker=IcyXADZASNSG9lYD_WMrXHsqiSRKyiIE1o-K6C_ozdx5FVb-L84J74VhQ6-XWS3Z) ![Relais Uffizi, Tailor made Hotel](https://images.trvl-media.com/lodging/3000000/2550000/2542800/2542717/3e59e5ae_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Relais Uffizi, Tailor made Hotel Historic Centre of Florence CA $2,167 per person Jan 5 - Jan 11 found 19 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Florence (FLR) 9.4/10 Exceptional! (120 reviews) Phenomenal location! Reviewed on Oct 18, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-05/2026-01-11/?FromAirport=YYZ&Destination=FLR&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2542717&paandie=true&dealMarker=IcyXADZASNSG9lYD_WMrXEsW-d5bSZDX0hKP6HIq4nXEmavdchEXK450rDEMegCR) ![Sina Villa Medici, Autograph Collection](https://images.trvl-media.com/lodging/1000000/20000/18300/18229/72404b44_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sina Villa Medici, Autograph Collection Historic Centre of Florence CA $2,215 per person Jan 12 - Jan 18 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Florence (FLR) 8.6/10 Excellent! (308 reviews) Staff was very helpful despite the hot weather. Great stay, very serene environment for vacation. Reviewed on Sep 28, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-12/2026-01-18/?FromAirport=YUL&Destination=FLR&NumRoom=1&NumAdult=2&NumChild=0&hotelId=18229&paandie=true&dealMarker=uFYi4Web8E_xB1SizqkjRbj0Cwl5sXRuJQnrFIw6c5Yvyyi1p186HK4NA786YCub) ![Hotel Caravaggio](https://images.trvl-media.com/lodging/2000000/1040000/1030500/1030408/108cda47_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Caravaggio Historic Centre of Florence CA $1,642 per person Jan 12 - Jan 18 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Florence (FLR) 9/10 Wonderful! (1,002 reviews) Friendly staff, great location, clean and comfortable rooms. Reviewed on Nov 22, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-12/2026-01-18/?FromAirport=YUL&Destination=FLR&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1030408&paandie=true&dealMarker=uFYi4Web8E_xB1SizqkjRaVzSlu4yW5zqGS4Lv9MgrvAaGp-zSOm4DfD5JHRdE6t) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=PKG_BF_PROMO_601360) ## 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 $414 CA $469 total Dec 21 - Dec 22 includes taxes & fees 9.8/10 Exceptional! (253 reviews) Our arrival experience was less than stellar for a warm welcome to property. Front desk associate was very cold and accusatory of the situation we encountered outside of the property. We have traveled extensively and I expected better arrival experience. It all changed for the better when we finally ... Reviewed on Nov 23, 2025 [](https://expedia.ca/Hotel-Search?startDate=21%2F12%2F2025&endDate=22%2F12%2F2025&selected=23264410&PinnedHotelID=23264410&HadPinnedHotel=true®ionId=601360) ![Hotel Italia](https://images.trvl-media.com/lodging/2000000/1670000/1664000/1663916/22c9fd1e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Italia Via Ghibellina 5/7 Cortona AR 9/10 Wonderful! (277 reviews) The personnel were warm and accommodating. The breakfast was amazing! The views were wonderful! Reviewed on Nov 14, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=10%2F12%2F2025&endDate=11%2F12%2F2025&selected=1663916&PinnedHotelID=1663916&HadPinnedHotel=true®ionId=601360) [](https://expedia.ca/Hotel-Search?startDate=10%2F12%2F2025&endDate=11%2F12%2F2025&selected=1663916&PinnedHotelID=1663916&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! (270 reviews) Very friendly and helpful staff. Nice rooms Reviewed on Sep 7, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=10%2F12%2F2025&endDate=11%2F12%2F2025&selected=984435&PinnedHotelID=984435&HadPinnedHotel=true®ionId=601360) [](https://expedia.ca/Hotel-Search?startDate=10%2F12%2F2025&endDate=11%2F12%2F2025&selected=984435&PinnedHotelID=984435&HadPinnedHotel=true®ionId=601360) [See all 1,249 properties in Cortona](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=27%2F11%2F2025&endDate=28%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 $145 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 $33 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 $41 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 - Lodging - Flights - Packages - Cars - Other ### Lodging - [Acquaviva Hotels](https://www.expedia.ca/Acquaviva-Hotels.d6047638.Travel-Guide-Hotels) - [Lgbt Friendly Hotels in Bettolle](https://www.expedia.ca/Bettolle-Hotels-LGBT-Friendly-Hotel.0-0-d6285815-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - [Bettolle Hotels](https://www.expedia.ca/Bettolle-Hotels.d6285815.Travel-Guide-Hotels) - [Brolio Hotels](https://www.expedia.ca/Brolio-Hotels.d6361222.Travel-Guide-Hotels) - [B&B in Camucia](https://www.expedia.ca/Camucia-Bed-And-Breakfast.d6289367-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Camucia Hotels](https://www.expedia.ca/Camucia-Hotels.d6289367.Travel-Guide-Hotels) - [Casa del Re Hotels](https://www.expedia.ca/Casa-Del-Re-Hotels.d6361319.Travel-Guide-Hotels) - [Castiglion Fiorentino Hotels](https://www.expedia.ca/Castiglion-Fiorentino-Hotels.d6047858.Travel-Guide-Hotels) - [Castroncello Hotels](https://www.expedia.ca/Castroncello-Hotels.d6361225.Travel-Guide-Hotels) - [Cesa Hotels](https://www.expedia.ca/Cesa-Hotels.d6361221.Travel-Guide-Hotels) - 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[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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)