Ossaia Vacation Packages

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Your Ossaia Vacation

Say farewell to the stress of planning and hello to a Ossaia vacation package. With the finer details organized before you go, you can focus on discovering this city, starting with Contrada Castello, which is good for dining, views and culture. A trip to Ossaia is a great opportunity to take in the sights. Check out well-known attractions like Villa Bramasole, Piazza della Repubblica and Cathedral of Cortona. Expedia has what you need to escape your routine. Tailor your vacation to Ossaia to suit your travel style, whatever that may be!

Top Ossaia Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Price was CA $2,260, price is now CA $1,471 per person
CA $1,471
per person
Aug 15 - Aug 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Florence (FLR)
7.4/10 Good! (1,014 reviews)
Room was clean, breakfast was decent. In general, it was a good stay. Would likely consider staying again.

Reviewed on Jun 30, 2026

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was CA $2,610, price is now CA $1,517 per person
CA $1,517
per person
Aug 31 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Florence (FLR)
7.6/10 Good! (1,004 reviews)
Highly recommended

Reviewed on Jun 30, 2026

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Price was CA $7,058, price is now CA $4,536 per person
CA $4,536
per person
Sep 6 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
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 Jun 19, 2026

Hotel San Luca

Hotel San Luca

4 out of 5
Cortona Old Town
Price was CA $2,056, price is now CA $1,501 per person
CA $1,501
per person
Sep 15 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
8.6/10 Excellent! (429 reviews)
Wonderful hotel with great view for Tuscany, good breakfast, perfect location to visit Cortona

Reviewed on Jun 30, 2026

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Price was CA $2,780, price is now CA $2,034 per person
CA $2,034
per person
Aug 31 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Florence (FLR)
9.6/10 Exceptional! (568 reviews)
Very nice and friendly staff, good breakfast, nice and clean hotel

Reviewed on Jun 18, 2026

Ready to book your vacation to Ossaia?

 

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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 CA $842 per night from Jul 14 to Jul 15
CA $842
CA $935 total
Jul 14 - Jul 15
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 Jun 19, 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 CA $129 per night from Jul 2 to Jul 3
CA $129
CA $151 total
Jul 2 - Jul 3
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 Dec 3, 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 CA $467 per night from Jul 30 to Jul 31
CA $467
CA $527 total
Jul 30 - Jul 31
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 Jun 29, 2026

Monastero di Cortona Hotel & Spa
See all 5,170 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

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

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

CA $140
per adult
98% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
Oil museum and oil mill in Tuscany: tour and tasting

Oil museum and oil mill in Tuscany: tour and tasting

CA $32
per adult
Oil museum and oil mill in Tuscany: tour and tasting
Tasting Tour in One of The Most Beautiful Cellars in the World

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

CA $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 vacation package cost?
You can snap up a vacation package to this popular destination from CA $1,471 on Expedia. However, how much your vacation to Ossaia costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Ossaia?
If you're looking to snag a cheap Ossaia vacation package, consider planning a trip in January, February and March. You'll typically find lower prices on flights and hotels during these quieter months — perfect for budget-conscious travellers.
How many days is enough for Ossaia?
Ossaia vacations come in various shapes and sizes, but to get a real feel for this place, we think 2 days is a good ballpark. In this timeframe, you can visit headline attractions like Eremo Le Celle and Belvedere and track down some underrated spots. Don't forget to visit neighbourhoods such as Cortona Old Town and Sodo either. If you plan wisely, you can even take a day trip or two from Ossaia too.
How to find the best Ossaia package deals?
Start your search for an Ossaia package deal by entering your destination and preferred trip dates under our "Packages" tab. Then add a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Ossaia package deal straight away, just switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Ossaia getaway off to a flying start.
Is it cheaper to book an Ossaia vacation as a package?
You can enjoy significant savings on your Ossaia retreat by booking a personalized vacation package. Check the "Package" heading, then select your travel dates and destination to view the best airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Ossaia?
If you're planning a spur-of-the-moment Ossaia getaway, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land awesome deals on your flights and hotels by booking well in advance.
How to plan a trip to Ossaia?

  1. Choose the perfect time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to travel to Ossaia.
  2. Plan your budget wisely: In addition to the cost of your stay, you'll need to factor in other expenses. These include food, transportation and flights. Also, put aside some extra funds for unexpected costs that may crop up during your trip to Ossaia.
  3. Decide how many days away: Start by compiling a list of the activities and attractions you'd like to get to in Ossaia. Then, estimate how long you'll need for each, including any travel time.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to pick an Ossaia vacation package that brings all your bookings together.

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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.