Ossaia Holidays from AU$3,747
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to AU$2,500 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 Holiday
Say goodbye to planning worries and hello to an Ossaia holiday package. With the finer details organised before you leave, you can focus on discovering the best of this city, starting with Contrada Castello, which is great for dining, views and culture. If a sightseeing tour is part of the plan during your trip to Ossaia, stop by well-known attractions like Villa Bramasole, Cathedral of Cortona and Piazza della Repubblica. Whoever you're taking time off with and whatever the size of your budget, your ultimate Ossaia holiday is only clicks away with Expedia.
The Latest Ossaia Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Villa Tolomei Hotel & Resort
Oltrarno
AU$3,800
per person
27 Sept - 3 Oct
found 1 day ago
Return direct flight included
Perth (PER) to Florence (FLR)
8.8/10 Excellent! (423 reviews)
Wonderful property, amazing hosts. 20 minutes outside of Florence center-easy to get a taxi. My family loved everything about our stay here!
Reviewed on 7 July 2026
Terme di Saturnia Natural Spa & Golf Resort - The Leading Hotels of the World
AU$4,092
per person
27 Sept - 3 Oct
found 1 day ago
Return direct flight included
Perth (PER) to Florence (FLR)
9.4/10 Exceptional! (496 reviews)
The staff and the look of the resort is top notch! The staff deserves 10 stars. We came for the springs and if you have not been to a pool fed from a sulfur spring, then you will be in shock like we were. We have been to many resorts with hot springs but not like this one. The pools and whole resort had a strong sulphur smell. It was even in our room which was far from the pool. There were flies everywhere, even while getting a massage, flies were buzzing and sometimes landing on me which cancelled out the relaxation of the massage. However, the resort is near the public and free falls/pools which enticed us to the area. For some reason, perhaps the flowing falls and cascading pools, there were not slime clumps floating around, no super strong sulphur smell there like at the resort. The pools should be cleaned of the floating debris more, overall, the top notch staff are amazing and the resort cannot help the way a natural sulphur spring smells or how it attracts flies.
Reviewed on 11 Aug 2026
Ossaia Holiday
Ossaia Essential Information
Language | Italian |
|---|---|
Currency | Euros |
Local Welcome | Ciao |
Local Goodbye | Ciao |
Population | 230 |
Max Temp Winter | 7ºC |
Max Temp Summer | 27ºC |
Top Sights | Cathedral of Cortona, Signorelli Theatre and Palazzo Comunale |
Our pick of the best Ossaia Hotel Deals
Precise Tale Poggio Alla Sala
Via Poggio alla Sala 10 Montepulciano SI
Fully refundableReserve now, pay when you stay
AU$824
18 Aug - 19 Aug
includes taxes & fees
9.6/10 Exceptional! (159 reviews)
"Precise Tale Poggio Alla Sala is a beautiful, peaceful property in a stunning and remote location near Montepulciano. The rooms and entire establishment were exceptionally clean and well maintained. The staff were friendly and welcoming, and the property is especially family- and kid-friendly, making ..."
Reviewed on 12 Aug 2026
Villa di Piazzano - Small Luxury Hotel of the World
Localita Piazzano, C.P. 6 Cortona AR
AU$1,105
4 Sept - 5 Sept
includes taxes & fees
Monastero di Cortona Hotel & Spa
Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
AU$477
23 Aug - 24 Aug
includes taxes & fees
10/10 Exceptional! (309 reviews)
"Hotel was perfect. Price was a bit high and very difficult parking"
Reviewed on 16 Aug 2026
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
Tasting Tour in One of The Most Beautiful Cellars in the World
AU$54
per adult
100% of travellers recommend
Montepulciano Wine Tasting in the Tuscan Countryside
AU$41
per adult
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
AU$153
per adult
98% of travellers recommend
Frequently asked questions
How much does an Ossaia holiday package cost?
You can snap up a holiday package to this top destination from AU$3,747 on Expedia. However, how much your holiday to Ossaia costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Ossaia?
You can typically find reduced prices and better availability in January, February and March. Take a look at our cheap Ossaia holiday packages and you could score some great off-season deals.
How many days is enough for Ossaia?
With a well-planned itinerary, you can easily hit the top Ossaia sights in a handful of days. But if you want to venture off the beaten track or go on day trips, think about booking your Ossaia holiday for longer.
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 holiday as a package?
You can enjoy significant savings on your Ossaia retreat by booking a personalised holiday 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 holiday package to Ossaia?
If you have your Ossaia holiday 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.
How to plan a trip to Ossaia?
- Pick your travel dates: The things you want to do in Ossaia and your preferred season can help you decide when to go.
- Budget wisely: On top of the cost of your accommodation, you should consider other expenses too. These include flights, food and transportation. Also, put aside some extra funds for unexpected costs that may crop up during your trip to Ossaia.
- Work out your trip length: Think about how much time you'd like to spend exploring Ossaia. Plan your itinerary so you can get to all the activities and attractions you're interested in without rushing.
- Combine your airfare and accommodation: Once you've settled on your trip dates and duration, lock in the perfect Ossaia holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
