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 $2,095, price is now CA $1,375 per person
CA $1,375
per person
Apr 3 - Apr 7
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Florence (FLR)
7.6/10 Good! (1,002 reviews)
Yes, to both questions. Wi-fi needs work.
Reviewed on Feb 7, 2026
Grand Hotel Cavour
Historic Centre of Florence
Price was CA $3,662, price is now CA $2,543 per person
CA $2,543
per person
May 1 - May 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.2/10 Wonderful! (1,002 reviews)
Everything was wonderful. The staff was so helpful. I didn’t eat breakfast so I don’t know how it was
Reviewed on Feb 10, 2026
Il Rivalta - Place of Charme
Historic Centre of Florence
Price was CA $3,505, price is now CA $2,469 per person
CA $2,469
per person
May 1 - May 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.2/10 Wonderful! (420 reviews)
Our room was lovely, clean and well appointed.
The staff were very friendly and very helpful!, breakfast was amazing, they cater for everyone.
The restaurant staff really friendly and accommodating, we had a birthday meal there which they made extra special too, and overall our stay was made better ( if that’s possible) due to the above. Grazie Mille.
Reviewed on Jan 29, 2026
Relais Uffizi, Tailor made Hotel
Historic Centre of Florence
Price was CA $3,223, price is now CA $2,336 per person
CA $2,336
per person
May 1 - May 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.4/10 Exceptional! (120 reviews)
Phenomenal location!
Reviewed on Oct 18, 2025
Hotel degli Orafi
Historic Centre of Florence
Price was CA $2,969, price is now CA $2,158 per person
CA $2,158
per person
Mar 21 - Mar 27
found 8 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Florence (FLR)
9.6/10 Exceptional! (1,001 reviews)
Very clean room and great amenities.
Reviewed on Jan 30, 2026
Ossaia Hotel Deals
Precise Tale Poggio Alla Sala
Via Poggio alla Sala 10 Montepulciano SI
9.4/10 Exceptional! (123 reviews)
Perfect escape
Fantastic hotel in an incredible setting. Staff were extremely helpful, attentive and understanding. The perfect location for a relaxing break and a centre for exploring Tuscany
Reviewed on Oct 27, 2025
Relais Villa Grazianella - UNA Esperienze
Via Grazianella 5 Montepulciano SI
The price is CA $269 per night from Mar 4 to Mar 5
CA $269
CA $302 total
Mar 4 - Mar 5
includes taxes & fees
9.6/10 Exceptional! (278 reviews)
Everything was perfect. Warm welcome, comfortable and spacious rooms, great breakfast. The staff was very kind and friendly. I also recommend the wine tasting experience. Highly recommended!
Reviewed on Dec 5, 2025
Monastero di Cortona Hotel & Spa
Via del Salvatore Cortona AR
The price is CA $394 per night from Mar 15 to Mar 16
CA $394
CA $440 total
Mar 15 - Mar 16
includes taxes & fees
9.8/10 Exceptional! (260 reviews)
Everything was great! Lovely hotel
Reviewed on Jan 4, 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 $115
per adult
100% of travellers recommend
Oil museum and oil mill in Tuscany: tour and tasting
CA $32
per adult
Montepulciano Wine Tasting in the Tuscan Countryside
CA $40
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.
