Ossaia Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to AED 148 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

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 AED 1,405 per night from Apr 8 to Apr 9
AED 1,405
AED 1,570 total
includes taxes & fees
8 Apr - 9 Apr
9.4/10 Exceptional! (76 reviews)
"Absolutely beautiful property with very friendly and helpful staff. They really took care of us during our short stay"

Reviewed on 20 March 2025

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
Fully refundableReserve now, pay when you stay
The price is AED 1,683 per night from Apr 8 to Apr 9
AED 1,683
AED 1,883 total
includes taxes & fees
8 Apr - 9 Apr
9.6/10 Exceptional! (200 reviews)
"The Villa di Piazzano is stunning down to the smallest detail. The staff is attentive, pleasant and helpful. The food and wine at the onsite restaurant was some of the best we had on our 23-day trip across Italy. One of our favorite stays for sure!"

Reviewed on 29 October 2024

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 AED 1,137 per night from Apr 23 to Apr 24
AED 1,137
AED 1,283 total
includes taxes & fees
23 Apr - 24 Apr
9.8/10 Exceptional! (205 reviews)
Good
"Super friendly service from most of the staff and beautiful property, restaurant and bars were great too."

Reviewed on 2 December 2024

Monastero di Cortona Hotel & Spa
See all 5,132 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 top destination 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 can typically find reduced prices and better availability in January, February and March. Take a look at our cheap Ossaia vacation packages and you could score some great off-season deals.
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.
How to plan a trip to Ossaia?

  1. Pick your travel dates: The things you want to do in Ossaia and your preferred season can help you decide when to go.
  2. Budget wisely: On top of the cost of your accommodations, 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.
  3. 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.
  4. Combine your airfare and accommodations: Once you’ve settled on your trip dates and duration, lock in the perfect Ossaia vacation package for you.

Discover the most popular places to visit in Ossaia

Cortona featuring heritage architecture

Piazza della Repubblica

5/5(4 reviews)

Find out about the history of Cortona with a stop at Piazza della Repubblica. Make time to visit the cathedral and monuments while you're in the area.

Piazza della Repubblica

Villa Bramasole

You can learn about the history of Cortona with a trip to Villa Bramasole. You can enjoy the wineries while in the area.

Villa Bramasole

Cortona Cathedral

Find out about the history of Cortona with a stop at Cortona Cathedral. Make time to visit the cathedral and monuments while you're in the area.

Cortona Cathedral