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&regionId=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&regionId=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&regionId=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&regionId=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)

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-   [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. Savings not available on all packages.

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