Title: Cortona Vacation Packages & Trips 2026 from CA $2,057 | 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.

![Eurostars Florence Boutique](https://images.trvl-media.com/lodging/2000000/1170000/1167000/1166901/10f2f159_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Eurostars Florence Boutique

Historic Centre of Florence

CA $2,057

per person

May 8 - May 14

found 2 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Florence (FLR)

8.6/10 Excellent! (476 reviews)

The room was clean and the staff very accommodating. The breakfast was quite sufficient and had a good variety. The location is great. It's a short walk from the square, shopping and from restaurants.

Reviewed on Dec 13, 2025

![Grand Hotel Cavour](https://images.trvl-media.com/lodging/1000000/20000/11000/10993/50470bbc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Grand Hotel Cavour

Historic Centre of Florence

CA $3,143

per person

May 10 - May 16

found 19 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Florence (FLR)

9.2/10 Wonderful! (1,002 reviews)

Everyone is so nice and helpful! It was also in a great location with an amazing rooftop picturing the entire city.

Reviewed on Feb 20, 2026

![Hotel Berchielli](https://images.trvl-media.com/lodging/1000000/530000/521300/521260/3061994d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Berchielli

Historic Centre of Florence

CA $3,267

per person

May 10 - May 16

found 20 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Florence (FLR)

9.4/10 Exceptional! (1,002 reviews)

Very good Breakfast with many food options. Great service !

Reviewed on Jan 21, 2026

![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 $2,841

per person

May 10 - May 16

found 19 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Florence (FLR)

8.8/10 Excellent! (939 reviews)

Great staff. Helpful. Clean

Reviewed on Feb 13, 2026

![LHP Hotel River & SPA](https://images.trvl-media.com/lodging/1000000/900000/892100/892069/fb677935_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### LHP Hotel River & SPA

Historic Centre of Florence

CA $3,124

per person

May 10 - May 16

found 19 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Florence (FLR)

8.8/10 Excellent! (243 reviews)

The rooms were clean and the staff was very friendly. Breakfast had a great variety of food to choose from and the staff was wonderful!

Reviewed on Nov 29, 2025

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale 

Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 

[Book now](https://expedia.ca/deals?rfrr=PKG_SPRING_PROMO_601360)

## 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

9.8/10 Exceptional! (228 reviews)

Room was wonderful, bathroom spacious and well appointed. Staff amazing and so friendly

Reviewed on Nov 6, 2025

[Get rates](https://expedia.ca/Hotel-Search?startDate=10%2F03%2F2026&endDate=11%2F03%2F2026&selected=971985&PinnedHotelID=971985&HadPinnedHotel=true&regionId=601360)

[](https://expedia.ca/Hotel-Search?startDate=10%2F03%2F2026&endDate=11%2F03%2F2026&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

CA $394

CA $440 total

Mar 22 - Mar 23

includes taxes & fees

[](https://expedia.ca/Hotel-Search?startDate=22%2F03%2F2026&endDate=23%2F03%2F2026&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

[Get rates](https://expedia.ca/Hotel-Search?startDate=10%2F03%2F2026&endDate=11%2F03%2F2026&selected=984435&PinnedHotelID=984435&HadPinnedHotel=true&regionId=601360)

[](https://expedia.ca/Hotel-Search?startDate=10%2F03%2F2026&endDate=11%2F03%2F2026&selected=984435&PinnedHotelID=984435&HadPinnedHotel=true&regionId=601360)

[See all 1,170 properties in Cortona](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=25%2F02%2F2026&endDate=26%2F02%2F2026&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 $115

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)

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- [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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