Ossaia Vacations from $887

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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 $1,462, price is now $887 per person
$887
per person
Sep 29 - Oct 3
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
7.4/10 Good! (1,008 reviews)
Good service and the room was clean

Reviewed on Jul 10, 2026

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $2,126, price is now $1,354 per person
$1,354
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,006 reviews)
It was great. I’ve just liked more variety in the breakfast. The location is good.

Reviewed on Jul 12, 2026

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Save 100% on your flight
Price was $4,329, price is now $2,771 per person
$2,771
per person
Aug 28 - Sep 3
found 12 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (147 reviews)

Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $2,500, price is now $1,668 per person
$1,668
per person
Oct 3 - Oct 9
found 11 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
8.8/10 Excellent! (1,002 reviews)
Excellent location! Rooftop lounge perfect for sunset!!

Reviewed on Jul 11, 2026

Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Price was $2,389, price is now $1,663 per person
$1,663
per person
Sep 15 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
8.6/10 Excellent! (491 reviews)
Very good location. Clean hotel. Our ac was broken but they handled us a new room inmediately. The hotel is confortable and size of the rooms are decent. Bigger than average in the area.

Reviewed on Jun 26, 2026

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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
Montepulciano: Winery Tour and Tasting

Montepulciano: Winery Tour and Tasting

$40
per adult
100% of travellers recommend
Montepulciano: Winery 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

$38
per adult
100% of travellers recommend
Tasting Tour in One of The Most Beautiful Cellars in the World
See all activities in Ossaia

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
$442 nightly
The price is $493 total per night from Aug 1 to Aug 2
$493 total
Aug 1 - Aug 2
Total with taxes and fees
Precise Tale Poggio Alla Sala
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
$633 nightly
The price is $705 total per night from Jul 31 to Aug 1
$705 total
Jul 31 - Aug 1
Total with taxes and fees
9.8/10 Exceptional! (240 reviews)
"10/10"

Reviewed on Jul 7, 2026

Villa di Piazzano - Small Luxury Hotel of the World
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
$91 nightly
The price is $106 total per night from Jul 14 to Jul 15
$106 total
Jul 14 - Jul 15
Total with taxes and 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
See all 5,155 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 $887 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.