Title: Cortona Vacation Packages & Trips 2025/2026 from CA $1,228 | 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. ![Residenza Hotel Cimabue](https://images.trvl-media.com/lodging/2000000/1080000/1074500/1074439/3373ee9a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Residenza Hotel Cimabue Historic Centre of Florence CA $1,228 per person Jan 10 - Jan 16 found 6 hours ago Roundtrip flight included Toronto (YYZ) to Florence (FLR) 7.6/10 Good! (367 reviews) It was just a short walk from the square and was so charming! I wish I would have had more time here, and the staff were so sweet and helpful! I would definitely recommend this hotel Reviewed on Oct 7, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-10/2026-01-16/?FromAirport=YYZ&Destination=FLR&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1074439&paandie=true&dealMarker=iyp8ikmAVQWH8RvZXyILtvtcpRoXJx9P8gB46jKNv4U8g1_zg5RNllFfQje-VeOG) ![Bernini Palace](https://images.trvl-media.com/lodging/1000000/20000/14000/13999/84743cc7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Bernini Palace Historic Centre of Florence CA $1,782 per person Dec 6 - Dec 12 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Florence (FLR) 9.6/10 Exceptional! (1,009 reviews) The property was elegant, convenient, and an oasis amidst the crowds in Florence. The service was impeccable and the rooms were very comfortable. An outstanding hotel in Florence! Wouldn't stay anywhere else! Reviewed on Oct 17, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-06/2025-12-12/?FromAirport=YUL&Destination=FLR&NumRoom=1&NumAdult=2&NumChild=0&hotelId=13999&paandie=true&dealMarker=JKUPZKKNmBnMmpOONQivhrsvfQvjmHh-Abt603k35Spdf_2a2eSnsXmuRBQYDrbQ) ![Hotel La Scaletta Al Ponte Vecchio](https://images.trvl-media.com/lodging/2000000/1610000/1604300/1604285/9b3b942d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel La Scaletta Al Ponte Vecchio Historic Centre of Florence CA $1,444 per person Jan 10 - Jan 16 found 6 hours ago Roundtrip flight included Toronto (YYZ) to Florence (FLR) 8.8/10 Excellent! (931 reviews) Amazing property & the staff is incredible.Love this place. Reviewed on Oct 18, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-10/2026-01-16/?FromAirport=YYZ&Destination=FLR&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1604285&paandie=true&dealMarker=iyp8ikmAVQWH8RvZXyILtgAuR4_25NL5Si5gBtE-zOP5R9bTlmGLEzGtHC6u2pHH) ![Hotel Duomo Firenze](https://images.trvl-media.com/lodging/3000000/2550000/2541700/2541603/fdd7cf48_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Duomo Firenze Historic Centre of Florence CA $1,484 per person Jan 7 - Jan 11 found 1 hour ago Roundtrip flight included Toronto (YYZ) to Florence (FLR) 9/10 Wonderful! (1,006 reviews) This was a fabulous, wonderful, magnificent property! It’s close to everything in the historic District. The people were very friendly and went above and beyond to help us we will certainly come again! Reviewed on Oct 18, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-07/2026-01-11/?FromAirport=YYZ&Destination=FLR&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2541603&paandie=true&dealMarker=D4O38uunHxh4wzGnEK6AH8D2KPUWqiw3gyG5vuV_881_-ZohARLn-N7N_lQ-AGkY) ![Villa Tolomei Hotel & Resort](https://images.trvl-media.com/lodging/6000000/5950000/5948900/5948813/10e274a0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Villa Tolomei Hotel & Resort Oltrarno CA $1,784 per person Nov 22 - Nov 28 found 8 hours ago Roundtrip flight included Toronto (YYZ) to Florence (FLR) 8.8/10 Excellent! (397 reviews) Great place to stay near Florence, it’s quite and relaxing. The pool is great. Reviewed on Jul 31, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-22/2025-11-28/?FromAirport=YYZ&Destination=FLR&NumRoom=1&NumAdult=2&NumChild=0&hotelId=5948813&paandie=true&dealMarker=Rr0THeiph2DjBonf87zyDA9UJg8cl_1twabHMle7YVTRVWJEiXOkQNbEmxYLv5yu) ## Ready to book your vacation to Cortona? Choose your dates ## Cortona Hotel Deals ![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 Fully refundableReserve now, pay when you stay CA $917 CA $1,021 total Oct 21 - Oct 22 includes taxes & fees 9.6/10 Exceptional! (226 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 [](https://expedia.ca/Hotel-Search?startDate=21%2F10%2F2025&endDate=22%2F10%2F2025&selected=971985&PinnedHotelID=971985&HadPinnedHotel=true®ionId=601360) ![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 $418 CA $466 total Nov 9 - Nov 10 includes taxes & fees 9.8/10 Exceptional! (244 reviews) "fabulous hotel with the most beautiful aperol spritz I have ever had served by the pool, and that was only one of the wonderful things I have to say about this beautiful hotel. The staff were helpful and accomodating, breakfast in the courtyard outstanding and our room was divine. Cant recommend ..." Reviewed on Oct 9, 2025 [](https://expedia.ca/Hotel-Search?startDate=09%2F11%2F2025&endDate=10%2F11%2F2025&selected=23264410&PinnedHotelID=23264410&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 Fully refundable CA $173 CA $204 total Oct 30 - Oct 31 includes taxes & fees 9/10 Wonderful! (267 reviews) "Very friendly and helpful staff. Nice rooms" Reviewed on Sep 7, 2025 [](https://expedia.ca/Hotel-Search?startDate=30%2F10%2F2025&endDate=31%2F10%2F2025&selected=984435&PinnedHotelID=984435&HadPinnedHotel=true®ionId=601360) [See all 1,291 properties in Cortona](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=21%2F10%2F2025&endDate=22%2F10%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 $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 $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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)