Ossaia Holidays

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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.

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

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 AU$947 per night from 16 July to 17 July
AU$947
16 July - 17 July
includes taxes & fees
9.6/10 Exceptional! (147 reviews)
"It’s a beautiful property, but be aware that it is secluded and that the restaurant menu is quite limited and after a couple of days, we were happy to go elsewhere. The waiting staff was attentive and nice, front desk not as much (maybe the la guard barrier?)"

Reviewed on 19 June 2026

Precise Tale Poggio Alla Sala
A Point Arezzo Park Hotel

A Point Arezzo Park Hotel

4 out of 5
Loc. Battifolle, 36/T Arezzo AR
Fully refundableReserve now, pay when you stay
The price is AU$154 per night from 5 July to 6 July
AU$154
5 July - 6 July
includes taxes & fees
7.6/10 Good! (165 reviews)
"Well, having travelled extensively for the past 13 years, this Hotel must be the coldest I have ever stayed in. It was December, but there was no heating on in the lobby area or the dining area so everyone had to wear coats or thick jumpers while eating their meals. The showers were not particularly ..."

Reviewed on 3 Dec 2025

A Point Arezzo Park Hotel
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 AU$536 per night from 29 July to 30 July
AU$536
29 July - 30 July
includes taxes & fees
10/10 Exceptional! (290 reviews)
"This is an excellent hotel, great staff, great location and great food. The breakfast is a really nice experience and the courtyard swimming pool is so peaceful."

Reviewed on 29 June 2026

Monastero di Cortona Hotel & Spa
See all 5,155 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.
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What to do in Ossaia

Montepulciano Wine Tasting in the Tuscan Countryside

Montepulciano Wine Tasting in the Tuscan Countryside

AU$41
per adult
Montepulciano Wine Tasting in the Tuscan Countryside
3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch

From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch

AU$141
per adult
98% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
Tasting Tour in One of The Most Beautiful Cellars in the World

Tasting Tour in One of The Most Beautiful Cellars in the World

AU$53
per adult
100% of travellers recommend
Tasting Tour in One of The Most Beautiful Cellars in the World
See all activities in Ossaia

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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.