Ossaia Vacations from $1,241

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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.
The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Price was $1,672, price is now $1,241 per person
$1,241
per person
Jan 6 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (485 reviews)
the hotel is located a little far from historic area of the town. but if you are a go walking person, it is 15 minutes walk. the hotel itself is very good. fresh and nice design, very nice buffet breakfast and kind stuff.

Reviewed on Oct 21, 2025

Collegio alla Querce, Auberge Collection

Collegio alla Querce, Auberge Collection

5 out of 5
Le Cure
Save 100% on your flight
Price was $3,278, price is now $2,308 per person
$2,308
per person
Jan 6 - Jan 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
10/10 Exceptional! (3 reviews)
The St. Regis Florence

The St. Regis Florence

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $2,438, price is now $1,719 per person
$1,719
per person
Jan 6 - Jan 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (261 reviews)
Nice property in a great location.

Reviewed on Jun 29, 2025

Villa Cora

Villa Cora

5 out of 5
Oltrarno
Save 100% on your flight
Price was $2,416, price is now $1,708 per person
$1,708
per person
Jan 6 - Jan 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
9.8/10 Exceptional! (465 reviews)
The hotel is very beautiful, and the surrounding environment is also excellent.

Reviewed on Sep 26, 2025

Portrait Firenze - Lungarno Collection

Portrait Firenze - Lungarno Collection

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $3,325, price is now $2,426 per person
$2,426
per person
Jan 6 - Jan 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
9.8/10 Exceptional! (297 reviews)
The hotel was very nice however there was construction below us. Additionally, the restaurant and bar were not open due to renovations.

Reviewed on Mar 5, 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

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

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

$104
per adult
100% 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

$23
per adult
Oil museum and oil mill in Tuscany: tour and tasting
See all activities in Ossaia

Ossaia Hotel Deals

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! (147 reviews)
Meh
This hotel has so much potential, but many details are missing. From music to create a pleasant atmosphere in the communal areas, especially restaurant and breakfast space. (So awkward to hear everyone chew their food around you and the kitchen staff comments in the background) To electrical jobs ...

Reviewed on Jul 3, 2025

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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
$275 nightly
The price is $307 total per night from Nov 11 to Nov 12
$307 total
Nov 11 - Nov 12
Total with taxes and fees
9.8/10 Exceptional! (247 reviews)
Excellent hotel Staff very knowledgeable and friendly Loved everything about our stay and will return.

Reviewed on Oct 25, 2025

Monastero di Cortona Hotel & Spa
Hotel Continentale

Hotel Continentale

4 out of 5
Piazza Guido Monaco, 7, Arezzo, AR
Fully refundableReserve now, pay when you stay
$125 nightly
The price is $149 total per night from Oct 30 to Oct 31
$149 total
Oct 30 - Oct 31
Total with taxes and fees
8.4/10 Very Good! (449 reviews)
We had a last-minute stay there due to the train strike, and it was a great evening after all… The hotel was right there in the main Square plus near the train station. The staff was lovely and they have the most beautiful rooftop patio and bar. you have to check out.

Reviewed on Oct 17, 2025

Hotel Continentale
See all 5,231 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 $1,241 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.