Ossaia Vacations from $969

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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
Save 100% on your flight
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,012 reviews)
Great location, right near the train station, and all the other major attractions in Florence. Rooms are small but the air conditioning was great!

Reviewed on Jul 19, 2025

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 26 - Oct 2
found 14 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.6/10 Exceptional! (462 reviews)
Hands down the best place we have stayed. They accommodated to go breakfasts for our tours, arranged taxis, made cappuccino when we were heading out the door. Wonderful experience

Reviewed on Jun 6, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,001 reviews)
The property looked to be in a weird area when I first booked but it was exactly the opposite. Just down the street was food and shopping and it was really close to a piazza.

Reviewed on Jul 19, 2025

Grand Hotel Cavour

Grand Hotel Cavour

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 22 - Sep 26
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.2/10 Wonderful! (1,002 reviews)
Excellent location right in the middle of everything. If thinking about using public transportation The hotel is on the C bus line these are small electric buses very difficult to get luggage on had to get a taxi

Reviewed on Jul 15, 2025

Tenuta di Artimino Member of Meliá Collection

Tenuta di Artimino Member of Meliá Collection

4 out of 5
Save 100% on your flight
per person
Sep 7 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.4/10 Exceptional! (117 reviews)
Rural area, quiet and quaint

Reviewed on Jul 10, 2025

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Discover the most popular places to visit in Ossaia

Cortona featuring heritage architecture

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

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

Cortona Cathedral

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

What to do in Ossaia

For your personal cooking class in Tuscany

Amazing four courses cooking class in Tuscany

$311
per adult
Amazing four courses cooking class in Tuscany
Cortona

Cortona Private Guided Tour

$304
per traveler
Cortona Private Guided Tour
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

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
$490 nightly
The price is $546 total per night from Aug 9 to Aug 10
$546 total
Aug 9 - Aug 10
Total includes taxes and fees
9.4/10 Exceptional! (100 reviews)
"beautiful property. Emanates "tuscany" amid garden and vineyards. Great villa with excellent and well chosen art. Very comfortable and quiet. Nice amenities. Would stay here again. Much appreciated it for its character and charm and of course service."

Reviewed on Jul 7, 2025

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
Fully refundableReserve now, pay when you stay
$581 nightly
The price is $649 total per night from Jul 20 to Jul 21
$649 total
Jul 20 - Jul 21
Total includes taxes and fees
9.6/10 Exceptional! (214 reviews)
"Would definitely come back! The Italian garden at the property is beautiful."

Reviewed on Jul 9, 2025

Villa di Piazzano - Small Luxury Hotel of the World
Nuovo Etruria Resort

Nuovo Etruria Resort

Via di S. Martino snc, Montepulciano, SI
Fully refundableReserve now, pay when you stay
$137 nightly
The price is $155 total per night from Jul 23 to Jul 24
$155 total
Jul 23 - Jul 24
Total includes taxes and fees
9.2/10 Wonderful! (20 reviews)
"Near town, not walkable to town"

Reviewed on Jul 14, 2025

Nuovo Etruria Resort
See all 5,293 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 $969 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.