Ossaia Holidays

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    Save up to S$1,300 when you book a flight and hotel together*

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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 S$796 per night from 31 Jul to 1 Aug
S$796
31 Jul - 1 Aug
includes taxes & fees
9.6/10 Exceptional! (154 reviews)
"Magical location, pools, staff, property."

Reviewed on 19 Jul, 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 S$916 per night from 25 Aug to 26 Aug
S$916
25 Aug - 26 Aug
includes taxes & fees
9.8/10 Exceptional! (241 reviews)
"Very clean and very quiet"

Reviewed on 15 Jul, 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 S$469 per night from 25 Aug to 26 Aug
S$469
25 Aug - 26 Aug
includes taxes & fees
10/10 Exceptional! (297 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 Jul, 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.

What to do in Ossaia

3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch

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

S$124
per adult
98% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
Horseback riding through the vineyards in Montepulciano Tuscany

Horseback riding through the vineyards in Montepulciano Tuscany

S$118
per adult
Horseback riding through the vineyards in Montepulciano Tuscany
Horseback riding in the hills of Montepulciano in Tuscany

Horseback riding in the hills of Montepulciano in Tuscany

S$118
per adult
Horseback riding in the hills of Montepulciano in Tuscany
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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.