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.
Aurum Firenze
Historic Centre of Florence
Price was CA $2,443, price is now CA $1,656 per person
CA $1,656
per person
Jul 7 - Jul 13
found 17 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Florence (FLR)
7.6/10 Good! (1,007 reviews)
Nice to have a safe and refrigerator. Breakfast had a nice choice but the room was small and you had to sign up for a time. Shower was so tiny that you couldn’t bend over and had no light. Bed had no blanket- just a sheet.
Reviewed on May 15, 2026
Aurum Uffizi
Historic Centre of Florence
Price was CA $2,465, price is now CA $1,665 per person
CA $1,665
per person
Jul 7 - Jul 13
found 17 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Florence (FLR)
7.6/10 Good! (1,006 reviews)
I had a wonderful stay at Aurum Uffizi. The staff were kind, friendly, and very helpful throughout my stay. The room was clean and comfortable, and the AC worked perfectly. The food was always fresh and enjoyable. Even though the hotel is close to shops, restaurants, and major tourist attractions, the area felt very safe and quiet, making it a perfect place to relax during my holiday. Highly recommended!
Reviewed on May 14, 2026
Il Rivalta - Place of Charme
Historic Centre of Florence
Price was CA $3,528, price is now CA $2,494 per person
CA $2,494
per person
Jun 24 - Jun 29
found 15 hours ago
Roundtrip flight included
Montreal (YMQ) to Florence (FLR)
9.2/10 Wonderful! (515 reviews)
Great location and hard to beat view. We stayed in the presidential suite but the bath tub drain wasn’t connected and so when my wife let the drain out, water went everywhere. They were apologetic and fixed it right away but for that kind of money, attention to detail is pretty important.
Reviewed on May 15, 2026
Hotel Duomo Firenze
Historic Centre of Florence
Price was CA $3,161, price is now CA $2,315 per person
CA $2,315
per person
Jul 7 - Jul 13
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.2/10 Wonderful! (1,003 reviews)
The staff was excellent! They were very accommodating! There was gelato and snacks available for free all day. The breakfast which was extra was amazing! The location was very convenient. Nothing but good things to say!
Reviewed on May 9, 2026
Il Malaspina
Historic Centre of Florence
Price was CA $2,860, price is now CA $2,099 per person
CA $2,099
per person
Jun 24 - Jun 29
found 15 hours ago
Roundtrip flight included
Montreal (YMQ) to Florence (FLR)
9.8/10 Exceptional! (95 reviews)
The staff were outstanding.
Got there 2 hours early to drop our cases and the receptionist found a room so we were able to check in early.
Very good location, quiet but close to centre and breakfast was amazing. Lovely touch having a coffee machine in our large and airy room.
Bathroom products smelt wonderful, apparently they are specially made for the hotel.
Would definitely stay here again.
Reviewed on May 15, 2026
Ossaia Hotel Deals
Villa di Piazzano - Small Luxury Hotel of the World
Localita Piazzano, C.P. 6 Cortona AR
The price is CA $1,044 per night from Jun 14 to Jun 15
CA $1,044
CA $1,161 total
Jun 14 - Jun 15
includes taxes & fees
9.8/10 Exceptional! (234 reviews)
The Hotel and grounds are beautiful and immaculately maintained. The entire staff really stands out. So friendly and welcoming. Those little gestures of respect and kindness are appreciated. Also it’s very convenient that they can speak English. There are several beautiful hotels in the area to experience, ...
Reviewed on May 14, 2026
Precise Tale Poggio Alla Sala
Via Poggio alla Sala 10 Montepulciano SI
Fully refundableReserve now, pay when you stay
The price is CA $637 per night from Jun 2 to Jun 3
CA $637
CA $710 total
Jun 2 - Jun 3
includes taxes & fees
9.4/10 Exceptional! (134 reviews)
Best hotel in city
Reviewed on May 14, 2026
Monastero di Cortona Hotel & Spa
Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
The price is CA $465 per night from May 24 to May 25
CA $465
CA $525 total
May 24 - May 25
includes taxes & fees
10/10 Exceptional! (274 reviews)
Everything was perfect. Customer service was everything. The classic room itself is slightly small, but a lovely big bathroom, and we were hoping for a view but understandably that would be the deluxe room. We used the spa amenities and it was pretty good for the price - recommended after a day or ...
Reviewed on May 9, 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
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
CA $176
per adult
98% of travellers recommend
Oil museum and oil mill in Tuscany: tour and tasting
CA $32
per adult
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
