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, 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.
Hotel Certosa Di Maggiano
CA $1,655
per person
Dec 6 - Dec 12
found 22 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
10/10 Exceptional! (217 reviews)
Our stay for our honeymoon was amazing. We loved our room and we were upgraded to a suite because they had it available. All the staff were kind and helpful. They carried our luggage up two flights of stairs to our room, helped make reservations, called taxis for us, etc.
The property was beautiful, maintained nicely, and was very quiet.
Really have no complaints. To note it is outside of city Centre of Siena so you will need taxis back and forth to the city for meals etc. which can get quite pricey so just plan ahead. Our room could’ve been cleaned a little better in between each day but overall it was still very clean. We would definitely stay there again!!
Reviewed on Sep 28, 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 $969
CA $1,078 total
Oct 20 - Oct 21
includes taxes & fees
9.8/10 Exceptional! (253 reviews)
"Stunning property; a real representation of Tuscany with the long driveway of tall trees; staff was amazing; food was excellent; gardens, picturesque! We would highly recommend! Overall amazing !!!"
Reviewed on Oct 5, 2026
Precise Tale Poggio Alla Sala
Via Di Poggio Alla Sala, 10 Montepulciano SI
9.6/10 Exceptional! (186 reviews)
"Stunningly beautiful resort for a 3 day getaway with my parents to experience the best of Tuscany - everything was perfect and pictures worth a thousand words!"
Reviewed on Oct 12, 2026
B&B Hotel Arezzo
Via Einstein, 4 Arezzo AR
CA $89
CA $107 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 $175
per adult
98% of travellers recommend
Montepulciano: Artisan Heroic Wine Tasting at the Terrace
CA $64
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 $1,242 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.
