Ossaia Vacations from $1,031
Book a Hotel + Flight or Car together to unlock savings
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!
The Latest Ossaia vacation packages
Price found within the past 48 hours. Click for updated prices.
Hotel Villa Liana
Historic Centre of Florence
$1,387
per person
Nov 21 - Nov 28
found 19 hours ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
8.8/10 Excellent! (369 reviews)
Hotel Eliana is a Gem! It’s a 20 minute walk from the center but I like it that way because it is quiet also after eating so much food from Central market I need to walk it down all the staff are very attentive, friendly and helpful. I will definitely go back in this hotel again. I have in fact, suggested this to my close friends who are coming to Italy next year 10 members of the family.
Reviewed on Oct 7, 2026
Grand Hotel Cavour
Historic Centre of Florence
$2,054
per person
Dec 28 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
9.4/10 Exceptional! (1,000 reviews)
Staff was friendly and accommodating! Rooms were very clean and SPACIOUS!
Would definitely return!
Reviewed on Oct 5, 2026
Eurostars Florence Boutique
Historic Centre of Florence
$1,292
per person
Nov 21 - Nov 28
found 19 hours ago
Roundtrip non-stop flight included
New York (JFK) 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
Hotel Ginori al DUOMO
Historic Centre of Florence
$1,432
per person
Nov 21 - Nov 28
found 19 hours ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
8.8/10 Excellent! (63 reviews)
The hotel is close to everything. Great restaurants near by too. Highly recommend.
Reviewed on Oct 5, 2026
What to do in Ossaia
Montepulciano Wine Tasting in the Tuscan Countryside
$29
per adult
Montepulciano: Winery Tour and Tasting
$40
per adult
100% of travellers recommend
Horseback riding through the vineyards in Montepulciano Tuscany
$92
per adult
Ossaia Hotel Deals
Villa di Piazzano - Small Luxury Hotel of the World
Localita Piazzano, C.P. 6 Cortona AR
$619 nightly
$690 total
Oct 20 - Oct 21
Total with taxes and 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
B&B Hotel Arezzo
Via Einstein, 4 Arezzo AR
Fully refundableReserve now, pay when you stay
$62 nightly
$75 total
Nov 8 - Nov 9
Total with taxes and 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.
Find the Best Ossaia Vacation Packages
Ossaia Essential Information
Language | Italian |
|---|---|
Currency | Euros |
Local Welcome | Ciao |
Local Goodbye | Ciao |
Population | 230 |
Max Temp Winter | 45ºF |
Max Temp Summer | 80ºF |
Top Sights | Signorelli Theatre, Cathedral of Cortona and Museum of the Etruscan Academy |
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Frequently asked questions
How much does an Ossaia vacation package cost?
You can snap up a vacation package to this top destination from $1,031 on Expedia. However, how much your vacation to Ossaia costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Ossaia?
You're likely to find lower rates and better availability in October, November and December. Browse our cheap Ossaia vacation packages and you could score some excellent off-season deals.
How many days is enough for Ossaia?
The ideal duration for your Ossaia vacation depends on what you'd like to do. Usually, a few days to a week will give you enough time to tick off all the top sights and discover some hidden gems along the way.
How to find the best Ossaia package deals?
Begin your search for an Ossaia package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply some filters, like "Property type" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Ossaia package deal right away, simply tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Ossaia adventure underway.
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. Click on the "Package" heading, then select your destination and travel dates to see some great flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Ossaia?
If you have your Ossaia vacation dates confirmed, book as early as you can to snap up some incredible deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for quick escapes.
Does Expedia offer Book Now, Pay Later Ossaia vacation packages?
If you're anything like us, you love jet-setting around the world but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the total cost of your Ossaia trip across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.