Ossaia Holidays

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Our pick of the best Ossaia Hotel Deals

Monastero di Cortona Hotel & Spa
Monastero di Cortona Hotel & Spa
5 out of 5
Via del Salvatore, Cortona
Fully refundableReserve now, pay when you stay
The price is NZ$535 per night from 23 Jun to 24 Jun
NZ$535
per night
23 Jun - 24 Jun
9.8/10 Exceptional! (167 reviews)
Gorgeous property
"What a beautiful place. Staff was amazing, so helpful in every way. Lovely breakfasts in the garden. Their bartender fixes some incredible cocktails and the one night we had dinner in the hotel restaurant, everything was delicious. A word of advice: If you’re driving, insist on a SMALL rental car. ..."

Reviewed on 1 Jun. 2024

Monastero di Cortona Hotel & Spa
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 NZ$901 per night from 16 Jun to 17 Jun
NZ$901
per night
16 Jun - 17 Jun
9.6/10 Exceptional! (176 reviews)
Amazing property, service and food!
"This hotel is one of the best we have experienced. The setting is beautiful, the room was very nice, the food was the best we had in Italy (and beyond) and the service is impeccable. The entire staff is amazing, but we wanted to point out the extra efforts from Paolo, Davide and Mikelo. Now we know ..."

Reviewed on 27 May 2024

Villa di Piazzano - Small Luxury Hotel of the World
Precise Tale Poggio Alla Sala
Precise Tale Poggio Alla Sala
5 out of 5
Via Poggio alla Sala 10, Montepulciano, Provincia di Siena
Fully refundableReserve now, pay when you stay
The price is NZ$982 per night from 19 Jun to 20 Jun
NZ$982
per night
19 Jun - 20 Jun
9.2/10 Wonderful! (39 reviews)
8th wonder of the world
"Absolutely amazing property with its own very authentic style. I loved the attention to detail that went into the design and creation of this experience. Special thanks to all the staff members that made this experience unforgettable. Bravo!"

Reviewed on 30 May 2024

Precise Tale Poggio Alla Sala
See all 5,346 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?
Choose from any combination of flights, hotels and car rentals, and you can be holidaying in Ossaia from just . And the more you bundle, the more dollars you save. The holiday of your dreams has never been more affordable.
How do I get a cheap travel package to Ossaia?
Search for flights that fit your busy schedule, add a hotel room to your booking and watch the savings grow with an Ossaia holiday package. It’s that easy! From hotels and flights to activities and rental cars, Expedia is where your cheap holiday begins. And with over 550 airlines and 1 000 000 hotels around the globe to select from, you won’t be short of choice.
Where should I stay in Ossaia?
With lots to explore in Ossaia, it’d be convenient for you to stay near its attractions. Villa Bramasole, Piazza della Repubblica and Cathedral of Cortona are some top ones to put on your itinerary.
What are the top hotels in Ossaia?
If this will be your first visit to Ossaia, book a room at Casa Lamate or Villa Il Trebbio. Both hotels offer comfy beds and are top options with lots of travellers.
How far in advance should I book my Ossaia holiday?
Search Expedia to compare international fares as early as possible. In most cases, you can purchase a seat up to a year before departure. If it’s too early for your preferred carrier, or you’re booking late, fear not. Low prices to Ossaia sometimes appear a few weeks before departure.
What does an Expedia Ossaia travel package include?
It comes down to what you’re after. If you’re travelling by yourself, you might decide to bundle hotels and flights. Taking the whole family to Ossaia? A travel package including rental cars, flights and hotels might be a better fit. Expedia gives you the freedom to build your own travel package.
What should I know before booking an Ossaia travel package?
Find deals that fit your budget with an Expedia package. Airfares, hotels, rental cars — we have everything you need to plan your break. You’ll save precious dollars just by bundling your bookings. Whether you’re going on a snow and ski adventure or kicking back on a warm beach, your perfect holiday is just a few clicks away.
Can I choose my airline with an Ossaia Expedia holiday package?
Yes, the choice is yours. Expedia has access to more than 550 partner airlines worldwide, so you can design your Ossaia getaway according to your budget and needs.
If I'm not able to travel, can I cancel my Ossaia holiday package?
It’s impossible to predict what the future holds, so it’s good to know that you can cancel or change your Ossaia holiday package. If you booked in the last 24 hours, you may be eligible for a refund. If it’s an older booking, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal for further details.

Discover the most popular places to visit in Ossaia

Image for Piazza della Repubblica

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
Image for Villa Bramasole

Villa Bramasole

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

Villa Bramasole
Image for Cathedral of Cortona

Cathedral of Cortona

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

Cathedral of Cortona

What to do in Ossaia

Image for Tuscany: Sanctuary of La Verna Day Tour Private Tour

Tuscany: Sanctuary of La Verna Day Tour Private Tour

NZ$789
Per adult
Tuscany: Sanctuary of La Verna Day Tour Private Tour
Image for Tasting Tour in One of The Most Beautiful Cellars in the World

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

NZ$49
Per adult
100% of travellers recommend
Tasting Tour in One of The Most Beautiful Cellars in the World
See all activities in Ossaia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.