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 $2,264, price is now CA $1,446 per person
CA $1,446
per person
Jul 13 - Jul 19
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Florence (FLR)
7.6/10 Good! (1,010 reviews)
The room smelled pretty bad even with the windows open. There's also a bunch of mosquitoes flying around, but everything else was ok!
Reviewed on May 27, 2026
Aurum Uffizi
Historic Centre of Florence
Price was CA $2,271, price is now CA $1,449 per person
CA $1,449
per person
Jul 13 - Jul 19
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Florence (FLR)
7.6/10 Good! (1,003 reviews)
Excelente servicio, las habitaciones las limpiaron todos los días, el desayuno muy completo, además muy cerca de plazas principales
Reviewed on May 27, 2026
Park Hotel Villa Ariston
Price was CA $3,946, price is now CA $2,526 per person
CA $2,526
per person
Jul 19 - Jul 25
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Florence (FLR)
8.8/10 Excellent! (129 reviews)
Highly recommend the Park Villa Ariston! The property is very clean and the staff are amazing. High praise for the breakfast and pool. We hope to return soon
Reviewed on May 14, 2026
Donati Luxury Tower Suites
Historic Centre of Florence
Price was CA $5,790, price is now CA $3,712 per person
CA $3,712
per person
Jul 19 - Jul 25
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.6/10 Exceptional! (63 reviews)
Agradable estancia. Excelente servicio. La habitación la mantenían siempre limpia. Todo queda cerca del área. Muy recomendable
Reviewed on May 23, 2026
Hotel Duomo Firenze
Historic Centre of Florence
Price was CA $2,707, price is now CA $1,833 per person
CA $1,833
per person
Jul 20 - Jul 24
found 6 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
9.2/10 Wonderful! (1,002 reviews)
Great spot. Free Gelato 24/7. Staff helpful. This location is the best I could choose.
Reviewed on May 26, 2026
Ossaia Hotel Deals
Villa di Piazzano - Small Luxury Hotel of the World
Localita Piazzano, C.P. 6 Cortona AR
The price is CA $972 per night from Jun 19 to Jun 20
CA $972
CA $1,082 total
Jun 19 - Jun 20
includes taxes & fees
9.8/10 Exceptional! (235 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
Monastero di Cortona Hotel & Spa
Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
The price is CA $579 per night from Jun 28 to Jun 29
CA $579
CA $650 total
Jun 28 - Jun 29
includes taxes & fees
10/10 Exceptional! (282 reviews)
"We had an amazing stay at the monastero di Cortona. The property is absolutely beautiful and impeccably maintained. The pool area is lovely and the views are unbelievable. The staff was super helpful and attentive- gave us recommendations for restaurants (and made reservations for us) and helped ..."
Reviewed on May 26, 2026
Precise Tale Poggio Alla Sala
Via Poggio alla Sala 10 Montepulciano SI
Fully refundableReserve now, pay when you stay
The price is CA $719 per night from Jun 11 to Jun 12
CA $719
CA $800 total
Jun 11 - Jun 12
includes taxes & fees
9.6/10 Exceptional! (139 reviews)
"Beautiful stay for our honeymoon. This is definitely a place to go and feel at peace in the Tuscan countryside. 15 min away from some wineries and 20 min away from Montepulciano. Great balance of feeling relaxed by the spa and pool with some quick getaways. Lastly, the restaurant was beyond excellent. ..."
Reviewed on May 23, 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.
