Title: Ossaia Vacation Packages & Trips 2026 from CA $2,048 | Expedia.ca

[Ossaia Travel Guide](https://expedia.ca/Ossaia.dx6361235)[Hotels in Ossaia](https://expedia.ca/Ossaia-Hotels.d6361235.Travel-Guide-Hotels)[Vacation Rentals in Ossaia](https://expedia.ca/Ossaia-Vacation-Rentals.d6361235.Travel-Guide-VacationRentals)[Ossaia Car Rentals](https://expedia.ca/Car-Rentals-In-Ossaia.d6361235.Car-Rental-Guide)

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# Ossaia Vacation Packages

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#### Your Ossaia Vacation

Say farewell to the stress of planning and hello to a Ossaia vacation package. With the finer details organized before you go, you can focus on discovering this city, starting with Contrada Castello, which is good for dining, views and culture. A trip to Ossaia is a great opportunity to take in the sights. Check out well-known attractions like [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). Expedia has what you need to escape your routine. Tailor your vacation to Ossaia to suit your travel style, whatever that may be!

## Top Ossaia Vacation Deals

Price found within the past 48 hours. Click for updated prices.

![Eurostars Florence Boutique](https://images.trvl-media.com/lodging/2000000/1170000/1167000/1166901/88283612_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Eurostars Florence Boutique

Historic Centre of Florence

CA $2,048

per person

Jun 17 - Jun 23

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Florence (FLR)

8.6/10 Excellent! (483 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

![Hotel Duomo Firenze](https://images.trvl-media.com/lodging/3000000/2550000/2541700/2541603/89ed1f8e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Duomo Firenze

Historic Centre of Florence

CA $2,339

per person

Jun 17 - Jun 23

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Florence (FLR)

9.2/10 Wonderful! (1,002 reviews)

Charming room directly across from the Duomo. Friendly, accommodating staff and the chef at the breakfast buffet is amazing! He made a cotton candy cappuccino! City center location close to restaurants, attractions and shopping. Also lively at night.

Reviewed on Mar 31, 2026

![Villa Cora](https://images.trvl-media.com/lodging/1000000/30000/22600/22579/01d144a6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Villa Cora

Oltrarno

CA $4,434

per person

May 14 - May 19

found 1 day ago

Roundtrip flight included

Ottawa (YOW) to Florence (FLR)

9.8/10 Exceptional! (472 reviews)

Amazing service and staff. Wow!

Reviewed on Feb 21, 2026

![Il Rivalta - Place of Charme](https://images.trvl-media.com/lodging/46000000/45800000/45790300/45790281/9555d572_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Il Rivalta - Place of Charme

Historic Centre of Florence

CA $2,657

per person

Jun 17 - Jun 23

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Florence (FLR)

9.2/10 Wonderful! (475 reviews)

Wonderful location and accommodations Breakfast buffet had everything you could want Beautiful view of the river and the bridges Could not have enjoyed it more!!!!

Reviewed on Apr 1, 2026

![The Moon Boutique Hotel & Spa](https://images.trvl-media.com/lodging/23000000/22260000/22255000/22254976/a69619e4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Moon Boutique Hotel & Spa

Historic Centre of Florence

CA $2,566

per person

Jun 22 - Jun 28

found 5 hours ago

Roundtrip non-stop flight included

Ottawa (YOW) to Florence (FLR)

9.6/10 Exceptional! (512 reviews)

Very nice - modern and clean hotel with great breakfast and very helpful staff. just outside the hotel there is a tram line and mini bus stand to commute the different parts of town. The only negative part was smaller room size but all other positive features of the hotel and staff overcomes this minor deficiency.

Reviewed on Mar 30, 2026

## Ready to book your vacation to Ossaia?

Choose your dates

## Ossaia Hotel Deals

![Villa di Piazzano - Small Luxury Hotel of the World](https://images.trvl-media.com/lodging/1000000/980000/972000/971985/c358cc6c_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Villa di Piazzano - Small Luxury Hotel of the World

Localita Piazzano, C.P. 6 Cortona AR

CA $817

CA $912 total

Apr 30 - May 1

includes taxes & fees

9.8/10 Exceptional! (228 reviews)

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

Reviewed on Nov 6, 2025

[](https://expedia.ca/Hotel-Search?startDate=30%2F04%2F2026&endDate=01%2F05%2F2026&selected=971985&PinnedHotelID=971985&HadPinnedHotel=true&regionId=6361235)

![Relais Villa Grazianella - UNA Esperienze](https://images.trvl-media.com/lodging/5000000/4320000/4310500/4310479/cd1e0f87_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Relais Villa Grazianella - UNA Esperienze

Via Grazianella 5 Montepulciano SI

Fully refundableReserve now, pay when you stay

CA $388

CA $433 total

Apr 12 - Apr 13

includes taxes & fees

9.8/10 Exceptional! (284 reviews)

Absolutely breathtaking property. The staff was extremely welcoming and helpful. Truly such a beautiful experience. Highly recommend to anyone

Reviewed on Mar 21, 2026

[](https://expedia.ca/Hotel-Search?startDate=12%2F04%2F2026&endDate=13%2F04%2F2026&selected=4310479&PinnedHotelID=4310479&HadPinnedHotel=true&regionId=6361235)

![Monastero di Cortona Hotel & Spa](https://images.trvl-media.com/lodging/24000000/23270000/23264500/23264410/b2055c17_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Monastero di Cortona Hotel & Spa

Via del Salvatore Cortona AR

Fully refundableReserve now, pay when you stay

CA $457

CA $516 total

Apr 30 - May 1

includes taxes & fees

[](https://expedia.ca/Hotel-Search?startDate=30%2F04%2F2026&endDate=01%2F05%2F2026&selected=23264410&PinnedHotelID=23264410&HadPinnedHotel=true&regionId=6361235)

[See all 5,099 properties in Ossaia](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=04%2F04%2F2026&endDate=05%2F04%2F2026&regionId=6361235)

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 Ossaia

![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 $124

per adult

**98%** 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 $31

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 $39

per adult

[](https://expedia.ca/things-to-do/montepulciano-wine-tasting-in-the-tuscan-countryside.a50286653.activity-details)

[See all activities in Ossaia](https://expedia.ca/things-to-do/search?rid=6361235)

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