Ossaia Vacations from $657

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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 $1,016, price is now $657 per person
$657
per person
Oct 31 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,000 reviews)
Right near the attractions. Easy to get around

Reviewed on Sep 4, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,762, price is now $1,044 per person
$1,044
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,000 reviews)
Good value for price and location.

Reviewed on Sep 8, 2025

Villa Cora

Villa Cora

5 out of 5
Oltrarno
Save 100% on your flight
Price was $2,927, price is now $1,750 per person
$1,750
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.8/10 Exceptional! (458 reviews)
Villa Cora was delightful in every way. The only negative thing I have to say is that I am not currently still there. Alas, I would highly recommend Villa Cora as a jumping off point for your Tuscan or Firenze adventures.

Reviewed on Sep 6, 2025

Hotel degli Orafi

Hotel degli Orafi

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $2,265, price is now $1,468 per person
$1,468
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (1,004 reviews)
The location was very easy to walk around and lots of places to eat.

Reviewed on Sep 9, 2025

Collegio alla Querce - Auberge Collection

Collegio alla Querce - Auberge Collection

5 out of 5
Le Cure
Save 100% on your flight
Price was $2,798, price is now $1,850 per person
$1,850
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
10/10 Exceptional! (3 reviews)
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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

For your personal cooking class in Tuscany

Amazing four courses cooking class in Tuscany

$257
per adult
Amazing four courses cooking class in Tuscany
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
Montepulciano: Wine Tour and tasting

Montepulciano: Wine Tour and tasting

$61
per adult
100% of travellers recommend
Montepulciano: Wine Tour and tasting
See all activities in Ossaia

Ossaia Hotel Deals

Hotel Panoramic

Hotel Panoramic

3 out of 5
Via di Villa Bianca, 8, Montepulciano, SI
$71 nightly
The price is $83 total per night from Oct 6 to Oct 7
$83 total
Oct 6 - Oct 7
Total with taxes and fees
8.6/10 Excellent! (247 reviews)
"Nice location. Staff was nice. The only issue is the room with no AC or plugs. When reviewing the property it appeared the property lists AC. You would assume the whole hotel has AC. Once I selected the room I should have looked closely at the AC availability. Rough night to sleep. Other than that ..."

Reviewed on Jul 26, 2025

Hotel Panoramic
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
$388 nightly
The price is $436 total per night from Oct 3 to Oct 4
$436 total
Oct 3 - Oct 4
Total with taxes and fees
9.8/10 Exceptional! (234 reviews)
"Very friendly staff at a beautiful property located in a great part of Cortona."

Reviewed on Sep 9, 2025

Monastero di Cortona Hotel & Spa
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
$471 nightly
The price is $526 total per night from Oct 5 to Oct 6
$526 total
Oct 5 - Oct 6
Total with taxes and fees
9.2/10 Wonderful! (108 reviews)
"10/10, would definitely recommend!"

Reviewed on Aug 15, 2025

Precise Tale Poggio Alla Sala
See all 5,313 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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Frequently asked questions

How much does an Ossaia vacation package cost?
You can snap up a vacation package to this top destination from $657 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.