Ossaia Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Ossaia

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 13.209.570 ₫ per night from 28 Jun to 29 Jun
13.209.570 ₫
14.711.177 ₫ total
28 Jun - 29 Jun
includes taxes & fees
9.2/10 Wonderful! (94 reviews)
"This place is absolutely stunning and tranquil, with many amenities to enjoy. The spa area is fantastic, and the room was spotless. The staff provided excellent service, and breakfast was simply amazing. I wish I had stayed longer. If I return to Tuscany someday, I would definitely choose to stay ..."

Reviewed on 21 Jun 2025

Precise Tale Poggio Alla Sala
Nuovo Etruria Resort
Nuovo Etruria Resort
Via di S. Martino snc, Montepulciano, SI
Fully refundableReserve now, pay when you stay
The price is 2.695.928 ₫ per night from 26 Jun to 27 Jun
2.695.928 ₫
3.085.954 ₫ total
26 Jun - 27 Jun
includes taxes & fees
9/10 Wonderful! (12 reviews)
"The room was very clean. The view from the room is stunning! It is very quiet and relaxing. The resort is facing Montepulciano! The staff is very nice and friendly. I highly recommend it."

Reviewed on 14 Jun 2025

Nuovo Etruria Resort
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 14.807.813 ₫ per night from 10 Jul to 11 Jul
14.807.813 ₫
16.529.461 ₫ total
10 Jul - 11 Jul
includes taxes & fees
9.6/10 Exceptional! (209 reviews)
"The service was excellent."

Reviewed on 7 Jun 2025

Villa di Piazzano - Small Luxury Hotel of the World
See all 5,234 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 holiday package cost?
You can snap up a holiday package to this top destination 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?

  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 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.
  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 accommodation: Once you've settled on your trip dates and duration, lock in the perfect Ossaia holiday package for you.

Popular places to visit

Cortona showing heritage architecture

Piazza della Repubblica

5/5(1 review)

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

Piazza della Repubblica

Cortona Cathedral

5/5(1 review)

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

Giuseppe Garibaldi Memorial

You can learn about the history of Cortona when you stop by Giuseppe Garibaldi Memorial. Experience the area's museums and musical theatre.

Giuseppe Garibaldi Memorial