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.
Hotel Miceli - Civico 50

Hotel Miceli - Civico 50

3 out of 5
Historic Centre of Florence
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
8.8/10 Excellent! (185 reviews)
There was no staff on-site when we arrived, but we had been in touch with the hotel via WhatsApp all day, and they were super helpful and friendly! Entering the building was very easy, but the 3-person elevator was just a little squished. The room was as expected - the only downside was that the shower was only cold water (after running it for a few minutes) and the sink in the bathroom was only hot water! The room was warm when we entered, but we turned the air conditioning up and it was perfect by the time we arrived back for bed. All-in-all, it was a good stay overnight!

Reviewed on Jun. 22, 2025

Palazzo Firenze by Baglioni Hotels & Resorts

Palazzo Firenze by Baglioni Hotels & Resorts

5 out of 5
Historic Centre of Florence
per person
Sep 8 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.4/10 Exceptional! (228 reviews)
I VERY MUCH ENJOYED THE STAY

Reviewed on Jul. 18, 2025

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
per person
Sep 18 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
7.6/10 Good! (1,012 reviews)
El hotel muy limpio, súper ubicado entre la estación del tren y el centro histórico. Muy cerca hay muchísimas opciones para comer. Aire acondicionado bueno, ventana hacia la calle. Lo único incómodo es el espacio de regadera que es pequeño, y cuesta bañarse.

Reviewed on Jul. 31, 2025

LHP River Club

LHP River Club

5 out of 5
Santa Croce
per person
Sep 11 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
No reviews
Dimora Palanca Boutique & SPA

Dimora Palanca Boutique & SPA

5 out of 5
Historic Centre of Florence
per person
Sep 8 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.4/10 Exceptional! (42 reviews)
The staff went out of their way to be helpful with all queries

Reviewed on Jun. 21, 2025

Ready to book your vacation to Ossaia?

 

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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
The price is CA $629 per night from Aug 28 to Aug 29
CA $629
CA $702 total
Aug 28 - Aug 29
includes taxes & fees
9.4/10 Exceptional! (104 reviews)
"The staff were incredibly kind and helpful. I got a flat tire the day I was leaving the hotel and the staff went above and beyond to help me get the tire fixed so I could be on my way. The hotel is beautiful and the food was excellent. I also requested a more private room and the staff changed the ..."

Reviewed on Jul. 19, 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
The price is CA $792 per night from Aug 6 to Aug 7
CA $792
CA $884 total
Aug 6 - Aug 7
includes taxes & fees
9.6/10 Exceptional! (217 reviews)
"AMAZING! Gorgeous! I would recommend to everyone!"

Reviewed on Jul. 29, 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
The price is CA $164 per night from Sep 1 to Sep 2
CA $164
CA $187 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (27 reviews)
"Highly recommend it!"

Reviewed on Jul. 28, 2025

Nuovo Etruria Resort
See all 5,276 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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What to do in Ossaia

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

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

CA $183
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

CA $32
per adult
Oil museum and oil mill in Tuscany: tour and tasting
Bottaia

Tasting Tour in One of The Most Beautiful Cellars in the World

CA $53
per adult
100% of travellers recommend
Tasting Tour in One of The Most Beautiful Cellars in the World
See all activities in Ossaia

Frequently asked questions

How much does an Ossaia vacation package cost?
You can snap up a vacation package to this popular destination from CA $1,424 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.