Ossaia Vacations from ￥303,582

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The Latest Ossaia Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

4 out of 5
Historic Centre of Florence
per person
Oct 4 - Oct 8
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Florence (FLR)
8.8/10 Excellent! (878 reviews)
Excellent location, well appointed nice rooms and spacious, good bathroom, walkable to all key places to visit in Florence, safe. Great breakfast buffet and rooftop terrace with drinks. Great gelato place right at the hotel. Location couldn't be better. Right next to Ponte Vecchio and walkable to all key attractions

Reviewed on Jul 14, 2025

Hotel L'Orologio Firenze

Hotel L'Orologio Firenze

4 out of 5
Historic Centre of Florence
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Florence (FLR)
9.6/10 Exceptional! (1,000 reviews)
Great location, good breakfast, very lovely rom and nice Staff

Reviewed on Jul 7, 2025

Hotel Balestri

Hotel Balestri

4 out of 5
Historic Centre of Florence
per person
Oct 4 - Oct 8
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Florence (FLR)
9.2/10 Wonderful! (956 reviews)
Loved the location and cleanliness, only complaint was the pillows and beds weren't comfortable. (Mattress were hard and pillows too thin)

Reviewed on Jul 16, 2025

The James Suite Hotel Firenze 1564 - Small Luxury Hotels of the World

The James Suite Hotel Firenze 1564 - Small Luxury Hotels of the World

5 out of 5
Historic Centre of Florence
per person
Sep 24 - Sep 30
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Florence (FLR)
No reviews
Hotel Miceli - Civico 50

Hotel Miceli - Civico 50

3 out of 5
Historic Centre of Florence
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Tokyo (TYO) 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

Find the Best Ossaia Vacation Packages

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 ￥75,913 per night from Aug 3 to Aug 4
￥75,913
￥84,542 total
Aug 3 - Aug 4
includes taxes & fees
9.4/10 Exceptional! (100 reviews)
"beautiful property. Emanates "tuscany" amid garden and vineyards. Great villa with excellent and well chosen art. Very comfortable and quiet. Nice amenities. Would stay here again. Much appreciated it for its character and charm and of course service."

Reviewed on Jul 7, 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 ￥86,507 per night from Aug 16 to Aug 17
￥86,507
￥96,542 total
Aug 16 - Aug 17
includes taxes & fees
9.6/10 Exceptional! (214 reviews)
"Would definitely come back! The Italian garden at the property is beautiful."

Reviewed on Jul 9, 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 ￥21,743 per night from Jul 23 to Jul 24
￥21,743
￥24,610 total
Jul 23 - Jul 24
includes taxes & fees
9.2/10 Wonderful! (20 reviews)
"Near town, not walkable to town"

Reviewed on Jul 14, 2025

Nuovo Etruria Resort
See all 5,293 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.

What to do in Ossaia

For your personal cooking class in Tuscany

Amazing four courses cooking class in Tuscany

￥45,562
per adult
Amazing four courses cooking class in Tuscany
Cortona

Cortona Private Guided Tour

￥44,703
per traveler
Cortona Private Guided Tour
3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch

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

￥16,677
per adult
100% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
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 top destination from ￥303,582 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 can typically find reduced prices and better availability in January, February and March. Take a look at our cheap Ossaia vacation packages and you could score some great off-season deals.
How many days is enough for Ossaia?
With a well-planned itinerary, you can easily hit the top Ossaia sights in a handful of days. But if you want to venture off the beaten track or go on day trips, think about booking your Ossaia vacation for longer.
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.
How to plan a trip to Ossaia?

  1. Pick your travel dates: The things you want to do in Ossaia and your preferred season can help you decide when to go.
  2. Budget wisely: On top of the cost of your accommodations, you should consider other expenses too. These include flights, food and transportation. Also, put aside some extra funds for unexpected costs that may crop up during your trip to Ossaia.
  3. Work out your trip length: Think about how much time you'd like to spend exploring Ossaia. Plan your itinerary so you can get to all the activities and attractions you're interested in without rushing.
  4. Combine your airfare and accommodations: Once you've settled on your trip dates and duration, lock in the perfect Ossaia vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.