Ossaia Vacations

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    Save up to AEDĀ 5,000 when you book a flight and hotel together*

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Find the Best Ossaia Vacation Packages

Ossaia Hotel Deals

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Via Poggio alla Sala 10 Montepulciano SI
Fully refundableReserve now, pay when you stay
The price is AEDĀ 2,603 per night from Jul 29 to Jul 30
AEDĀ 2,603
AEDĀ 2,889 total
29 Jul - 30 Jul
includes taxes & fees
9.6/10 Exceptional! (154 reviews)
"Magical location, pools, staff, property."

Reviewed on 19 July 2026

Precise Tale Poggio Alla Sala
Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

5 out of 5
Localita Piazzano, C.P. 6 Cortona AR
The price is AEDĀ 2,524 per night from Aug 18 to Aug 19
AEDĀ 2,524
AEDĀ 2,810 total
18 Aug - 19 Aug
includes taxes & fees
9.8/10 Exceptional! (241 reviews)
"Very clean and very quiet"

Reviewed on 15 July 2026

Villa di Piazzano - Small Luxury Hotel of the World
Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
The price is AEDĀ 1,363 per night from Aug 16 to Aug 17
AEDĀ 1,363
AEDĀ 1,533 total
16 Aug - 17 Aug
includes taxes & fees
10/10 Exceptional! (296 reviews)
"The food was amazing in the hotel. Staff was amazing. We felt at home from the moment we walked in. The amenities were wonderful."

Reviewed on 14 July 2026

Monastero di Cortona Hotel & Spa
See all 5,167 properties in Ossaia
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.

Frequently asked questions

How much does an Ossaia vacation package cost?
You can snap up a vacation package to this popular destination 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 ā€” perfect for budget-conscious travelers.
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?

  1. Choose the perfect time to travel: Your schedule, favorite season and the type of weather you enjoy can all influence your decision on when to travel to Ossaia.
  2. 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.
  3. 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.
  4. 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.