Ossaia Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 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
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Top Flight + Hotel Deals in Ossaia
Price found within the past 48 hours. Click for updated prices.
The Hoxton, Florence
Historic Centre of Florence
€673
per person
28 Sept - 30 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
9.4/10 Exceptional! (333 reviews)
I recommend this stay, to anyone going to Florence. This hotel is very nice and the staff was amazing
Reviewed on 27 Aug 2026
Dimora Palanca Boutique & SPA
Historic Centre of Florence
€751
per person
28 Sept - 30 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
9.2/10 Wonderful! (68 reviews)
This hotel is definitely not 5*, no amenities provided, very poor breakfast, like at 3* hotel, room was full of dark black hair, and most important pay attention to the location , as it’s in central station area, and we felt unsafe to walk there in the evening
Reviewed on 27 Aug 2026
Top hotels in Ossaia
Precise Tale Poggio Alla Sala
Via Poggio alla Sala 10 Montepulciano SI
Fully refundableReserve now, pay when you stay
€568
31 Aug - 1 Sept
includes taxes & fees
Villa di Piazzano - Small Luxury Hotel of the World
Localita Piazzano, C.P. 6 Cortona AR
€677
4 Sept - 5 Sept
includes taxes & fees
9.8/10 Exceptional! (245 reviews)
"Staff was helpful , and the room was clean. The Antica Casina di Caccia dining with wine pairing was absolutely amazing. Also took some great pictures in the garden. The breakfast was nice too."
Reviewed on 17 Aug 2026
Monastero di Cortona Hotel & Spa
Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
€330
30 Aug - 31 Aug
includes taxes & fees
10/10 Exceptional! (318 reviews)
"Before I share, I will say that the staff helping with breakfast and at the bar (by the pool) were great. However, the front desk employees were pretty cold in each of my interactions with them. When I first inquired about reserving time slots at the spa, I asked about the remaining available slots ..."
Reviewed on 29 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
€33
per adult
100% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
€84
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 €599 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.
