Title: Cortona Vacation Packages & Trips 2025/2026 from CA $1,404 | 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 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 $1,404 per person Nov 1 - Nov 7 found 21 hours ago Roundtrip flight included Toronto (YTO) to Florence (FLR) 7.8/10 Good! (1,000 reviews) Asking for extra towels was like asking for money. Amenities were limited such as a kettle. I got sick and needed warm water but their machine was turned off at night and no kettle available for the room. Less storage Reviewed on Sep 17, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-01/2025-11-07/?FromAirport=YTO&Destination=FLR&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2541615&paandie=true&dealMarker=JIjQ9H2VzQi7AlnxVYnN86ZH7jc7pR16c3g5Dr9p4PfiVWp9q6zXq-k8B9j5wyVA) ![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 $1,622 per person Nov 1 - Nov 7 found 21 hours ago Roundtrip flight included Toronto (YTO) to Florence (FLR) 9.6/10 Exceptional! (470 reviews) Room as immaculately clean. Steam shower was amazing. A little annoyed about the A/C, it turns off when you leave the room, so it didn’t stay cool in our room when we were gonna all day. Spa access was a lil confusing, it wasn’t use as you wish, you had to reserve a slot in a 3hr window which was at dinner time. This resulted in us only using the spa once. Breakfast had a wide selection, with a small cook to order menu. Was delicious and quick. Bed was extremely comfortable. Tram station for the T2 line was right in front of the hotel, when coming from the airport you have change T1 line to T2 line, but very simple. Reviewed on Sep 14, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-01/2025-11-07/?FromAirport=YTO&Destination=FLR&NumRoom=1&NumAdult=2&NumChild=0&hotelId=22254976&paandie=true&dealMarker=JIjQ9H2VzQi7AlnxVYnN87acVjeV1rBOt2P820XKJzENlovdDAxmAEY7SO7PxLgG) ![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 $1,609 per person Nov 2 - Nov 8 found 21 hours ago Roundtrip non-stop flight included Toronto (YTO) to Florence (FLR) 7.6/10 Good! (1,000 reviews) Hotel location is excellent. Near Firenze SMN station and all tourists attraction can be reached by walking. Small room size, no fridge/kettle in the room. Bed is comfortable but pillows are flat. Good breakfast. Reviewed on Sep 19, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-02/2025-11-08/?FromAirport=YTO&Destination=FLR&NumRoom=1&NumAdult=2&NumChild=0&hotelId=28961941&paandie=true&dealMarker=JIjQ9H2VzQi7AlnxVYnN8w9dE5mXxY49ak5dY9P0F3k6nWNg4VinOYRLDua78StN) ![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 $2,016 per person Nov 1 - Nov 7 found 21 hours ago Roundtrip flight included Toronto (YTO) to Florence (FLR) 9.6/10 Exceptional! (1,001 reviews) Right in the centre of activity. Very walkable and nice hotel. Staff was very helpful and attentive and room was nice and clean. Enjoyed our stay. Reviewed on Sep 15, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-01/2025-11-07/?FromAirport=YTO&Destination=FLR&NumRoom=1&NumAdult=2&NumChild=0&hotelId=13999&paandie=true&dealMarker=rKE9dYtXZQW0XjdDGADOtZKa2JGAGGduz32tc9o-Sqqp9Yrbfx4cO6RmvozJxtf0) ![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 $1,741 per person Nov 1 - Nov 7 found 21 hours ago Roundtrip flight included Toronto (YTO) to Florence (FLR) 8.8/10 Excellent! (907 reviews) Nice hotel Really great restaurant Reviewed on Sep 18, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-01/2025-11-07/?FromAirport=YTO&Destination=FLR&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1604285&paandie=true&dealMarker=rKE9dYtXZQW0XjdDGADOtWxahLp2VSwIY5jKaDNJc8motLnkIQnEp_wvpHWciSw1) ## 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 $679 CA $760 total Oct 20 - Oct 21 includes taxes & fees 9.8/10 Exceptional! (222 reviews) "If you like a peaceful quiet getaway this is the place!" Reviewed on Sep 9, 2025 [](https://expedia.ca/Hotel-Search?startDate=20%2F10%2F2025&endDate=21%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 $512 CA $576 total Oct 19 - Oct 20 includes taxes & fees 9.8/10 Exceptional! (235 reviews) "Great hotel but room 114 is too close to the bar area and as such very noisy if there are loud guests in there. I’d suggest a room away from the bar if you want a good nights sleep but everything else is fantastic" Reviewed on Sep 16, 2025 [](https://expedia.ca/Hotel-Search?startDate=19%2F10%2F2025&endDate=20%2F10%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 $197 CA $230 total Sep 23 - Sep 24 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=23%2F09%2F2025&endDate=24%2F09%2F2025&selected=984435&PinnedHotelID=984435&HadPinnedHotel=true®ionId=601360) [See all 1,300 properties in Cortona](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=20%2F09%2F2025&endDate=21%2F09%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 $143 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) ![Montepulciano: Wine Tour and tasting](https://mediaim.expedia.com/localexpert/47725497/a9b3d024-2644-4069-bba1-f4d1273546b5.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Montepulciano: Wine Tour and tasting CA $83 per adult **100%** of travellers recommend [](https://expedia.ca/things-to-do/montepulciano-wine-tour-and-tasting.a47725497.activity-details) ![Montepulciano: Tuscan Winery Tour with Wine Tasting & Meal](https://mediaim.expedia.com/localexpert/47474223/85eab411-f97a-42b2-93d4-e727692cded8.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Montepulciano: Tuscan Winery Tour with Wine Tasting & Meal CA $159 per adult **100%** of travellers recommend [](https://expedia.ca/things-to-do/montepulciano-tuscan-winery-tour-with-wine-tasting-meal.a47474223.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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)