
Cortona Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Cortona Vacation
With plenty of highlights as well as hidden gems, this city is best experienced with a Cortona vacation package. Find a place to stay in Contrada Castello, which is good for dining, views and culture. Ready to explore? Villa Bramasole, Piazza della Repubblica and Cathedral of Cortona are just a few of the top-rated places to visit during your trip to Cortona. Whoever you're going away with and whatever the size of your budget, your ultimate Cortona vacation is only clicks away with Expedia.
Top Cortona Vacation Deals
Price found within the past 48 hours. Click for updated prices.

Hotel La Scaletta Al Ponte Vecchio
Historic Centre of Florence
Price was CA $2,519, price is now CA $1,841 per person
CA $1,841
per person
May 17 - May 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
8.8/10 Excellent! (965 reviews)
The staff at breakfast prepare plain scrambled eggs for our 7 month old son and were very sweet! This our second time staying here and we absolutely love the hotel. Location, views, comfort. 10/10!
Reviewed on Feb 28, 2026

Eurostars Florence Boutique
Historic Centre of Florence
Price was CA $2,906, price is now CA $1,960 per person
CA $1,960
per person
Apr 20 - Apr 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
8.6/10 Excellent! (483 reviews)
The room was clean and the staff very accommodating. The breakfast was quite sufficient and had a good variety. The location is great. It's a short walk from the square, shopping and from restaurants.
Reviewed on Dec 13, 2025

Hotel Alessandra
Historic Centre of Florence
Price was CA $2,755, price is now CA $1,959 per person
CA $1,959
per person
May 20 - May 26
found 4 hours ago
Roundtrip flight included
Montreal (YUL) to Florence (FLR)
9.2/10 Wonderful! (849 reviews)
Clean room, amazing staff, location is great
Reviewed on Feb 2, 2026

Il Rivalta - Place of Charme
Historic Centre of Florence
Price was CA $3,887, price is now CA $2,801 per person
CA $2,801
per person
May 17 - May 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
9.2/10 Wonderful! (472 reviews)
Staff was extremely attentive
Reviewed on Mar 4, 2026
Cortona Hotel Deals

Villa di Piazzano - Small Luxury Hotel of the World
Localita Piazzano, C.P. 6 Cortona AR
The price is CA $947 per night from Mar 28 to Mar 29
CA $947
CA $1,048 total
Mar 28 - Mar 29
includes taxes & fees
9.8/10 Exceptional! (228 reviews)
Room was wonderful, bathroom spacious and well appointed. Staff amazing and so friendly
Reviewed on Nov 6, 2025

Monastero di Cortona Hotel & Spa
Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
The price is CA $388 per night from Mar 15 to Mar 16
CA $388
CA $433 total
Mar 15 - Mar 16
includes taxes & fees

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 Cortona

From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
CA $127
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
Explore a world of travel with Expedia
- Acquaviva Hotels
- Lgbt Friendly Hotels in Bettolle
- Bettolle Hotels
- Brolio Hotels
- B&B in Camucia
- Camucia Hotels
- Casa del Re Hotels
- Castiglion Fiorentino Hotels
- Castroncello Hotels
- Cesa Hotels
- Cignano Hotels
- Cortona Old Town Hotels
- Lgbt Friendly Hotels in Foiano della Chiana
- Foiano della Chiana Hotels
- Fossa del Lupo Hotels
- Fratticciola Hotels
- Gracciano Hotels
- Il Borgo Hotels
- La Strada-Santa Cristina Hotels
- Lucignano Hotels
- Marciano della Chiana Hotels
- Mercatale di Cortona Hotels
- Monsigliolo Hotels
- Montagnano Hotels
- Montalla Hotels
- Montecchio Del Loto Hotels
- Montecchio Hotels
- Montepulciano Stazione Hotels
- Rv Parks in Montepulciano Stazione
- Ossaia Hotels
- Palazzo del Pero Hotels
- Pergo Hotels
- Lgbt Friendly Hotels in Pieve a Quarto
- Polvano Hotels
- Portole Hotels
- Riccio Hotels
- Rigutino Hotels
- Hotels near Santa Margherita Basilica
- Santa Maria Hotels
- Sodo Hotels
- Terontola Hotels
- Torrita di Siena Hotels
- Hotels near Valdichiana Outlet Village
- Valiano Hotels
- Arezzo Vacations
- Art Studio di Adelina Quadri
- Bagni San Filippo Vacations
- Brunello di Montalcino Wine Area Vacations
- Visit Camucia
- Cantina del Redi
- Castelnuovo di Subbiano
- Church of San Sigismondo
- Church of Santa Maria della Pieve
- Church of St. Augustine
- Consorzio del Vino Nobile di Montepulciano
- Crete Senesi Vacations
- Visit Creti
- Croce del Pratomagno
- Fortress of Montalcino
- Le Miccine
- Visit Marciano della Chiana
- Visit Mercatale di Cortona
- Visit Metelliano
- Visit Montagnano
- Montalcino Vacations
- Visit Montepulciano Stazione
- Montepulciano Vacations
- Murlo Vacations
- Visit Ossaia
- Palazzo Ricci
- Piazza Grande
- Pienza Cathedral
- Pienza Vacations
- Piscine Termali Theia
- Visit Portole
- Visit Potassa
- Visit Rigutino
- San Donato Hospital
- Visit San Pietro a Cegliolo
- Visit Sinalunga
- Visit Tegoleto
- Tenuta Greppo Franco Biondi Santi
- Tenuta Valdipiatta
- Terme di Montepulciano Spa
- Visit Terontola
- Val d'Orcia Vacations
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.









