Ossaia Holidays

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Top hotels in Ossaia

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 S$433 per night from 27 Oct to 28 Oct
S$433
per night
27 Oct - 28 Oct
9.8/10 Exceptional! (194 reviews)
"Former monastery turned into a beautiful hotel with great views of Tuscan old town and countryside. Be prepared for an exciting adventure winding thru narrow medieval streets! Great staff!"

Reviewed on 27 Sep,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 S$778 per night from 29 Oct to 30 Oct
S$778
per night
29 Oct - 30 Oct
9.6/10 Exceptional! (196 reviews)
"Stunning romantic hotel in a beautiful setting. Lovely rooms, gardens, and pool. The food was lovely and the staff amazing. My only complaint was an added charge for any a la carte items in the breakfast which is included in the hotel charge. For the type and cost of the hotel, this should be ..."

Reviewed on 18 Sep,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 S$592 per night from 20 Oct to 21 Oct
S$592
per night
20 Oct - 21 Oct
9.2/10 Wonderful! (69 reviews)
Magical hotel in Tuscany
"One of the best hotels I have stayed in. Absolutely breathtaking grounds and beautiful chic interiors. Everywhere you look just takes your breath away. Luxurious amenities use and generous breakfast. We really appreciated the extra small touches eg mini notes, biscotti in the room and farewell gift ..."

Reviewed on 24 Sep,2024

Precise Tale Poggio Alla Sala
See all 5,518 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.

Popular places to visit

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 Cortona Cathedral

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
Image for Eremo Le Celle

Eremo Le Celle

Learn about the local history of Cortona with a stop at Eremo Le Celle. You can enjoy the wineries while in the area.

Eremo Le Celle

What to do in Ossaia

Image for Cortona: Pasta and Pizza Cooking Class

Cortona: Pasta and Pizza Cooking Class

S$159
Per adult
100% of travellers recommend
Cortona: Pasta and Pizza Cooking Class
Image for Tuscany: Sanctuary of La Verna Day Tour Private Tour

Tuscany: Sanctuary of La Verna Day Tour Private Tour

S$647
Per adult
Tuscany: Sanctuary of La Verna Day Tour Private Tour
Image for From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch

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

S$153
Per adult
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
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.