Ossaia Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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, Piazza della Repubblica and Cathedral of Cortona. 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
Historic Centre of Florence
CA $1,676
per person
Jan 9 - Jan 16
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Florence (FLR)
8.6/10 Excellent! (503 reviews)
The bed was comfortable but low to the floor. The shower was very slippery and could have used a shower mat. The breakfast was great. The staff were very nice and helpful.
Reviewed on Oct 10, 2026
The Moon Boutique Hotel & Spa
Historic Centre of Florence
CA $2,077
per person
Jan 9 - Jan 16
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Florence (FLR)
9.6/10 Exceptional! (605 reviews)
Everything was wonderful about our stay at The Moon Hotel and Spa. The room was beautiful and clean, the staff were friendly and helpful and it was a great location for sightseeing in Florence. We especially appreciated the very generous breakfast that was always served efficiently and with a smile. We would definitely stay again.
Reviewed on Oct 23, 2026
Bernini Palace
Historic Centre of Florence
CA $2,132
per person
Jan 9 - Jan 16
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Florence (FLR)
9.8/10 Exceptional! (1,006 reviews)
Had a fantastic stay at Bernini Palace. Our room was extremely comfortable and beautifully appointed. The public spaces are beautiful. Service was excellent. Breakfast in the beautiful breakfast room was divine. The location of the hotel was central and a stone's throw from Piazza della Signoria. I would absolutely stay here again!
Reviewed on Oct 23, 2026
Plaza Hotel Lucchesi
Historic Centre of Florence
CA $1,924
per person
Jan 9 - Jan 16
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Florence (FLR)
9.4/10 Exceptional! (1,002 reviews)
Hotel was wonderful. Stayed in the superior room which had a beautiful view over the city. Staff were incredibly helpful and the rooftop bar was fantastic.
Reviewed on Oct 21, 2026
Ready to book your vacation to Ossaia?
Ossaia Hotel Deals
Villa di Piazzano - Small Luxury Hotel of the World
Localita Piazzano, C.P. 6 Cortona AR
CA $954
CA $1,062 total
Oct 25 - Oct 26
includes taxes & fees
Precise Tale Poggio Alla Sala
Via Di Poggio Alla Sala, 10 Montepulciano SI
B&B Hotel Arezzo
Via Einstein, 4 Arezzo AR
Fully refundableReserve now, pay when you stay
CA $88
CA $106 total
Nov 8 - Nov 9
includes taxes & fees
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.
What to do in Ossaia
Montepulciano Wine Tasting in the Tuscan Countryside
CA $40
per adult
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
CA $189
per adult
98% of travellers recommend
Vino Nobile di Montepulciano winery tour and tasting
CA $48
per adult
Frequently asked questions
How much does an Ossaia vacation package cost?
You can snap up a vacation package to this popular destination from CA $1,676 on Expedia. However, how much your vacation to Ossaia costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Ossaia?
If you're looking to snag a cheap Ossaia vacation package, consider planning a trip in January, February and March. You'll typically find lower prices on flights and hotels during these quieter months — perfect for budget-conscious travellers.
How many days is enough for Ossaia?
Ossaia vacations come in various shapes and sizes, but to get a real feel for this place, we think 2 days is a good ballpark. In this timeframe, you can visit headline attractions like Eremo Le Celle and Belvedere and track down some underrated spots. Don't forget to visit neighbourhoods such as Cortona Old Town and Sodo either. If you plan wisely, you can even take a day trip or two from Ossaia too.
How to find the best Ossaia package deals?
Start your search for an Ossaia package deal by entering your destination and preferred trip dates under our "Packages" tab. Then add a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Ossaia package deal straight away, just switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Ossaia getaway off to a flying start.
Is it cheaper to book an Ossaia vacation as a package?
You can enjoy significant savings on your Ossaia retreat by booking a personalized vacation package. Check the "Package" heading, then select your travel dates and destination to view the best airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Ossaia?
If you're planning a spur-of-the-moment Ossaia getaway, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land awesome deals on your flights and hotels by booking well in advance.
How to plan a trip to Ossaia?
- Choose the perfect time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to travel to Ossaia.
- Plan your budget wisely: In addition to the cost of your stay, you'll need to factor in other expenses. These include food, transportation and flights. Also, put aside some extra funds for unexpected costs that may crop up during your trip to Ossaia.
- Decide how many days away: Start by compiling a list of the activities and attractions you'd like to get to in Ossaia. Then, estimate how long you'll need for each, including any travel time.
- Bundle your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to pick an Ossaia vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
