Ossaia Holidays

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Top Flight + Hotel Deals in Ossaia

Price found within the past 48 hours. Click for updated prices.
Hotel Villa Marsili

Hotel Villa Marsili

4 out of 5
Cortona Old Town
Save 100% on your flight
Price was €703, price is now €436 per person
€436
per person
25 Sept - 30 Sept
found 16 hours ago
Return flight included
Dublin (DUB) to Florence (FLR)
10/10 Exceptional! (305 reviews)
This hotel gets 5 stars in my book. The staff was welcoming as soon as we arrived and continued to be help throughout our stay. The rooms were old world elegant and so clean. The breakfast was world class, we have never had such large selections of food that were extremely delicious. They really go above and beyond to treat each of their guests like royalty.

Reviewed on 18 Aug 2025

Hotel Bencista

Hotel Bencista

3 out of 5
Save 100% on your flight
Price was €1,014, price is now €530 per person
€530
per person
19 Sept - 26 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
7.4/10 Good! (13 reviews)
Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was €1,126, price is now €612 per person
€612
per person
26 Sept - 29 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
7.8/10 Good! (1,000 reviews)
In my particular case, I tink is a good hotel , I would like the breakfast has more options. Probably I comeback next time.

Reviewed on 18 Aug 2025

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was €915, price is now €528 per person
€528
per person
26 Sept - 29 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
7.6/10 Good! (1,007 reviews)
Great location. Few minutes away from train station. Not so quiet. You could hear people from outside even the windows closed. If you are staying for a few days, it’s a great location.

Reviewed on 14 Aug 2025

LHP River Club

LHP River Club

5 out of 5
Santa Croce
Save 100% on your flight
Price was €850, price is now €570 per person
€570
per person
26 Sept - 29 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
10/10 Exceptional! (1 review)

Top hotels in Ossaia

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 €288 per night from 24 Aug to 25 Aug
€288
24 Aug - 25 Aug
includes taxes & fees
9.8/10 Exceptional! (230 reviews)
"Beautiful property, magical, great friendly staff, fantastic breakfast. Everything was perfect"

Reviewed on 7 Aug 2025

Monastero di Cortona Hotel & Spa
A Point Arezzo Park Hotel

A Point Arezzo Park Hotel

4 out of 5
Loc. Battifolle, 36/T, A1 exit Arezzo, Arezzo, AR
Fully refundableReserve now, pay when you stay
7.6/10 Good! (141 reviews)
"It is very close to autostrada,which is good if you have car. The Breakfast was excellant,with a wonderful hostess. This lady is a big bonus to this hotel.The air-conditioning is building controlled,which would not suit everyone.The cleaner for our area had poor attention to detail. The lead cleaner ..."

Reviewed on 24 Sep 2024

Get rates
A Point Arezzo Park Hotel
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 €564 per night from 23 Aug to 24 Aug
€564
23 Aug - 24 Aug
includes taxes & fees
9.6/10 Exceptional! (218 reviews)
"AMAZING! Gorgeous! I would recommend to everyone!"

Reviewed on 29 Jul 2025

Villa di Piazzano - Small Luxury Hotel of the World
See all 5,290 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.

Popular places to visit

Farneta Abbey

Find out about the history of Farneta when you take a trip to Farneta Abbey. While you're here, you can savour the wineries.

Farneta Abbey

What to do in Ossaia

Cortona

Cortona Private Guided Tour

€260
per traveller
Cortona Private Guided Tour
For your personal cooking class in Tuscany

Amazing four courses cooking class in Tuscany

€265
per adult
Amazing four courses cooking class in Tuscany
3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch

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

€114
per adult
100% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
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 from €436 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.