Ossaia Vacations from $1,378

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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!

The Latest Ossaia vacation packages

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 $2,090, price is now $1,378 per person
$1,378
per person
Jun 3 - Jun 9
found 16 hours ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
7.6/10 Good! (1,006 reviews)
Great simple place.

Reviewed on Apr 9, 2026

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $2,473, price is now $1,522 per person
$1,522
per person
Jun 3 - Jun 9
found 17 hours ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
7.6/10 Good! (1,000 reviews)
The room was clean and newly renovated. Having breakfast included was great for a quick bite so I could focus on exploring instead of searching and waiting in line. Would definitely recommend a stay here

Reviewed on Apr 9, 2026

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Save 100% on your flight
Price was $4,770, price is now $3,027 per person
$3,027
per person
May 24 - May 29
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
9.4/10 Exceptional! (124 reviews)
Most gorgeous setting, lovely staff and delicious food. We will definitely be back!

Reviewed on Apr 5, 2026

Portrait Firenze - Lungarno Collection

Portrait Firenze - Lungarno Collection

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $6,294, price is now $4,493 per person
$4,493
per person
Jun 3 - Jun 9
found 17 hours ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
9.8/10 Exceptional! (307 reviews)
The rooms are beautiful and immaculately kept. The staff is so personable and thoughtful. The location is unmatched highly recommend this hotel!

Reviewed on Apr 3, 2026

Hotel Balestri

Hotel Balestri

4 out of 5
Historic Centre of Florence
Price was $3,243, price is now $2,393 per person
$2,393
per person
Jun 3 - Jun 9
found 17 hours ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
9.2/10 Wonderful! (1,003 reviews)
Great location right on the water. Beautiful property, room was amazing, great views. Staff was super friendly and everything was perfect! Will definitely come back here again!!!

Reviewed on Apr 6, 2026

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Discover the most popular places to visit in Ossaia

Villa Bramasole

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

Villa Bramasole

Piazza della Repubblica

5/5(4 reviews)

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

Piazza della Repubblica

Cortona Cathedral

Cortona Cathedral is just one of the places to see in Cortona, so why not enjoy the other things to explore during your travels? Experience the area's museums and musical theater.

Cortona Cathedral

What to do in Ossaia

Montepulciano Wine Tasting in the Tuscan Countryside

Montepulciano Wine Tasting in the Tuscan Countryside

$29
per adult
Montepulciano Wine Tasting in the Tuscan Countryside
Tasting Tour in One of The Most Beautiful Cellars in the World

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

$38
per adult
100% of travellers recommend
Tasting Tour in One of The Most Beautiful Cellars in the World
Montepulciano Gran Tour

Montepulciano Gran Tour

$17
per adult
Montepulciano Gran Tour
See all activities in Ossaia

Ossaia Hotel Deals

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
$639 nightly
The price is $712 total per night from Apr 14 to Apr 15
$712 total
Apr 14 - Apr 15
Total with taxes and fees
9.8/10 Exceptional! (229 reviews)
We really enjoyed the hotel, very clean, good atmosphere!!!

Reviewed on Apr 10, 2026

Villa di Piazzano - Small Luxury Hotel of the World
Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze

Via Grazianella 5 Montepulciano SI
Fully refundableReserve now, pay when you stay
$254 nightly
The price is $285 total per night from Apr 13 to Apr 14
$285 total
Apr 13 - Apr 14
Total with taxes and fees
9.8/10 Exceptional! (284 reviews)
Absolutely breathtaking property. The staff was extremely welcoming and helpful. Truly such a beautiful experience. Highly recommend to anyone

Reviewed on Mar 21, 2026

Relais Villa Grazianella - UNA Esperienze
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
$305 nightly
The price is $345 total per night from Apr 19 to Apr 20
$345 total
Apr 19 - Apr 20
Total with taxes and fees
10/10 Exceptional! (262 reviews)
I did not drive to or from the hotel.

Reviewed on Apr 8, 2026

Monastero di Cortona Hotel & Spa
See all 5,073 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.

Find the Best Ossaia Vacation Packages

Ossaia Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Population
230
Max Temp Winter
45ºF
Max Temp Summer
80ºF
Top Sights
Signorelli Theatre, Cathedral of Cortona and Museum of the Etruscan Academy

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Frequently asked questions

How much does an Ossaia vacation package cost?
You can snap up a vacation package to this top destination from $1,378 on Expedia. However, how much your vacation to Ossaia costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Ossaia?
You're likely to find lower rates and better availability in October, November and December. Browse our cheap Ossaia vacation packages and you could score some excellent off-season deals.
How many days is enough for Ossaia?
The ideal duration for your Ossaia vacation depends on what you'd like to do. Usually, a few days to a week will give you enough time to tick off all the top sights and discover some hidden gems along the way.
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 vacation as a package?
You can enjoy significant savings on your Ossaia retreat by booking a personalized vacation 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 vacation package to Ossaia?
If you have your Ossaia vacation 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.
Does Expedia offer Book Now, Pay Later Ossaia vacation packages?
If you're anything like us, you love jet-setting around the world but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the total cost of your Ossaia trip across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.