Ossaia Vacations from $1,114
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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.
Dimora Palanca Boutique & SPA
Historic Centre of Florence
$1,114
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.2/10 Wonderful! (68 reviews)
This hotel is definitely not 5*, no amenities provided, very poor breakfast, like at 3* hotel, room was full of dark black hair, and most important pay attention to the location , as it’s in central station area, and we felt unsafe to walk there in the evening
Reviewed on Aug 27, 2026
Eden Rock Resort
$1,556
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.8/10 Exceptional! (109 reviews)
This was a beautiful property about 10 mins away from Florence. You get the beauty of Tuscany without having to go too far. The hotel only has 12 rooms and everyone knows you by name. We traveled with 2 kids and the rooms were very spacious. Staff are wonderful, Onsite restaurant was great. Views were breathtaking. We didn't have a car, and the hotel was able to help us with cabs easily. Service was excellent and we would highly recommend this hotel!
Reviewed on Jul 18, 2026
What to do in Ossaia
Tasting Tour in One of The Most Beautiful Cellars in the World
$38
per adult
100% of travellers recommend
Montepulciano Wine Tasting in the Tuscan Countryside
$29
per adult
Montepulciano: Winery Tour and Tasting
$40
per adult
100% of travellers recommend
Ossaia Hotel Deals
Precise Tale Poggio Alla Sala
Via Poggio alla Sala 10 Montepulciano SI
Fully refundableReserve now, pay when you stay
$535 nightly
$595 total
Aug 29 - Aug 30
Total with taxes and fees
9.6/10 Exceptional! (163 reviews)
"Amazing! If you are a family visiting Tuscany I highly recommend"
Reviewed on Aug 27, 2026
Villa di Piazzano - Small Luxury Hotel of the World
Localita Piazzano, C.P. 6 Cortona AR
$702 nightly
$782 total
Sep 3 - Sep 4
Total with taxes and fees
9.8/10 Exceptional! (245 reviews)
"Staff was helpful , and the room was clean. The Antica Casina di Caccia dining with wine pairing was absolutely amazing. Also took some great pictures in the garden. The breakfast was nice too."
Reviewed on Aug 17, 2026
Monastero di Cortona Hotel & Spa
Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
$352 nightly
$397 total
Aug 30 - Aug 31
Total with taxes and fees
10/10 Exceptional! (316 reviews)
"Amazing!!!! Very well kept place, the staff treats you like family. Room was cleaned fast in the morning. Restaurant and bar staff as well were amazing. The pool area is good vibes and the drinks and really good too 👍👍 I would definitely come back."
Reviewed on Aug 21, 2026
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 $1,114 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.
