Ossaia Vacation Packages
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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!
Top Ossaia Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Eden Rock Resort
CA $1,531
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip flight included
Toronto (YYZ) 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
Ready to book your vacation to Ossaia?
Ossaia Hotel Deals
Precise Tale Poggio Alla Sala
Via Poggio alla Sala 10 Montepulciano SI
Fully refundableReserve now, pay when you stay
CA $741
CA $825 total
Aug 29 - Aug 30
includes taxes & 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
CA $981
CA $1,092 total
Sep 3 - Sep 4
includes taxes & 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
CA $473
CA $533 total
Aug 30 - Aug 31
includes taxes & 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.
What to do in Ossaia
Tasting Tour in One of The Most Beautiful Cellars in the World
CA $53
per adult
100% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
CA $136
per adult
98% of travellers recommend
Oil museum and oil mill in Tuscany: tour and tasting
CA $32
per adult
Frequently asked questions
How much does an Ossaia vacation package cost?
You can snap up a vacation package to this popular destination from CA $1,531 on Expedia. However, how much your vacation to Ossaia costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Ossaia?
If you're looking to snag a cheap Ossaia vacation package, consider planning a trip in January, February and March. You'll typically find lower prices on flights and hotels during these quieter months — perfect for budget-conscious travellers.
How many days is enough for Ossaia?
Ossaia vacations come in various shapes and sizes, but to get a real feel for this place, we think 2 days is a good ballpark. In this timeframe, you can visit headline attractions like Eremo Le Celle and Belvedere and track down some underrated spots. Don't forget to visit neighbourhoods such as Cortona Old Town and Sodo either. If you plan wisely, you can even take a day trip or two from Ossaia too.
How to find the best Ossaia package deals?
Start your search for an Ossaia package deal by entering your destination and preferred trip dates under our "Packages" tab. Then add a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Ossaia package deal straight away, just switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Ossaia getaway off to a flying start.
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. Check the "Package" heading, then select your travel dates and destination to view the best airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Ossaia?
If you're planning a spur-of-the-moment Ossaia getaway, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land awesome deals on your flights and hotels by booking well in advance.
How to plan a trip to Ossaia?
- Choose the perfect time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to travel to Ossaia.
- Plan your budget wisely: In addition to the cost of your stay, you'll need to factor in other expenses. These include food, transportation and flights. Also, put aside some extra funds for unexpected costs that may crop up during your trip to Ossaia.
- Decide how many days away: Start by compiling a list of the activities and attractions you'd like to get to in Ossaia. Then, estimate how long you'll need for each, including any travel time.
- Bundle your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to pick an Ossaia vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
