Cortona Old Town Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*

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Top Holiday Package Deals in Cortona Old Town

Price found within the past 48 hours. Click for updated prices.
Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Price was CA $2,470, price is now CA $1,521 per person
CA $1,521
per person
Jun 3 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
7.6/10 Good! (1,006 reviews)
Great simple place.

Reviewed on Apr 9, 2026

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was CA $2,999, price is now CA $1,729 per person
CA $1,729
per person
Jun 3 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
7.6/10 Good! (1,000 reviews)
The room was clean and newly renovated. Having breakfast included was great for a quick bite so I could focus on exploring instead of searching and waiting in line. Would definitely recommend a stay here

Reviewed on Apr 9, 2026

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Price was CA $3,064, price is now CA $2,072 per person
CA $2,072
per person
May 26 - May 28
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Florence (FLR)
9.4/10 Exceptional! (124 reviews)
Most gorgeous setting, lovely staff and delicious food. We will definitely be back!

Reviewed on Apr 5, 2026

Grand Hotel Cavour

Grand Hotel Cavour

4 out of 5
Historic Centre of Florence
Price was CA $3,652, price is now CA $2,724 per person
CA $2,724
per person
Jun 23 - Jun 27
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
9.2/10 Wonderful! (1,000 reviews)
Staff is excellent…rooftop barter and server are extra special they are so friendly.

Reviewed on Apr 11, 2026

EXE Toscana

EXE Toscana

4 out of 5
Lucca Historical Center
Price was CA $2,788, price is now CA $2,081 per person
CA $2,081
per person
Jun 23 - Jun 27
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Florence (FLR)
8.4/10 Very Good! (822 reviews)
Great option for traveling in car around Tuscany. The best staff

Reviewed on Oct 21, 2025

Cortona Old Town Hotel Deals

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
The price is CA $496 per night from Apr 19 to Apr 20
CA $496
CA $558 total
Apr 19 - Apr 20
includes taxes & fees
10/10 Exceptional! (262 reviews)
I did not drive to or from the hotel.

Reviewed on Apr 8, 2026

Monastero di Cortona Hotel & Spa
Hotel San Michele

Hotel San Michele

4 out of 5
Via Guelfa 15 Cortona AR
Fully refundableReserve now, pay when you stay
The price is CA $198 per night from Apr 15 to Apr 16
CA $198
CA $231 total
Apr 15 - Apr 16
includes taxes & fees
Hotel San Michele
Hotel Villa Marsili

Hotel Villa Marsili

4 out of 5
Viale Cesare Battisti 13 Cortona AR
Fully refundableReserve now, pay when you stay
The price is CA $238 per night from Apr 17 to Apr 18
CA $238
CA $275 total
Apr 17 - Apr 18
includes taxes & fees
10/10 Exceptional! (325 reviews)
Need to take a taxi to hotel or bus and walk several minutes. Bus takes credit card. But hotel is very charming and lots of hospitality

Reviewed on Mar 29, 2026

Hotel Villa Marsili
See all 5,020 properties in Cortona Old Town
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.
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Frequently asked questions

How much does a Cortona Old Town vacation package cost?
From as little as CA $1,521. Yes, you read that correctly. Our Cortona Old Town packages are the quickest way to make your dollar go further. Combine your preferred hotels, flights and rental car and get out and see this wonderful destination.
How do I get a cheap travel package to Cortona Old Town?
Bundle your flights and hotels with Expedia to save big bucks on your next getaway. With more than 550 partner airlines and 1,000,000 hotel options globally, your Cortona Old Town vacation package can be tailored exactly to suit your travel style. With all that extra money, why not include some exciting activities and tours? It's an easy way to unlock even more savings. Your dream vacation in Cortona Old Town is much closer than you thought!
Where should I stay in Cortona Old Town?
A vacation in Cortona Old Town isn't complete without paying a visit to Villa Bramasole, Piazza della Repubblica and Cathedral of Cortona. Spend your evenings near these attractions and make sightseeing simple.
What are the top hotels in Cortona Old Town?
Elegante Appartamento Nel Centro Storico Di Cortona and Giotto Lovely Apartment In The City Center are a couple of the most sought-after hotels in Cortona Old Town. Why not take a look at the amenities and rates at each and then decide?
How far in advance should I book my Cortona Old Town vacation?
Be rewarded with the widest variety at the lowest prices by booking your adventure to Cortona Old Town early. Air carriers tend to release flight tickets anywhere up to a year before departure, so secure your spot as soon as possible. That being said, Expedia is dedicated to providing you with the best bargains around, so it's never a bad time to book your dream vacation!
What does an Expedia Cortona Old Town travel package include?
From flights and hotels to car rentals, Expedia can help you create a Cortona Old Town package that's ideal for you. Heading off for a week or two? Give some thought to a hotel, flight and rental car bundle. If you're taking a short break, a flight and hotel deal may suit you better. Activities can also be added after you've booked. Our packages make it a cinch to save and plan.
What should I know before booking a Cortona Old Town travel package?
Locking in all the parts of your trip together is one of the best ways to save. Bundle car rentals, airfares and hotels into a convenient little package. But you're not restricted to hotels. Expedia offers all types of properties, including vacation rentals such as beachside villas and serviced residences. The list is almost endless!
Can I choose my airline with a Cortona Old Town Expedia vacation package?
Definitely. Expedia has more than 550 partner airlines to select from worldwide. With all that choice at your fingertips, finding the right carrier to whisk you away to Cortona Old Town won't be difficult.
If I'm not able to travel, can I cancel my Cortona Old Town vacation package?
If your travel plans in Cortona Old Town have changed, it's a relief to know that you can cancel your booking. If you booked less than 24 hours ago, you may be eligible to receive a refund. If your booking is older than that, your airline, hotel or car rental company may charge fees. For more details, visit our Customer Service Portal.

Things to do

Pasta or Pizza cooking class in Cortona, vegetarian and vegan

Pasta or Pizza cooking class in Cortona, vegetarian and vegan

CA $189
per adult
Pasta or Pizza cooking class in Cortona, vegetarian and vegan
Cortona: Tagliatelle, Ravioli, and Tiramisu Cooking Class

Cortona: Tagliatelle, Ravioli, and Tiramisu Cooking Class

CA $229
per adult
Cortona: Tagliatelle, Ravioli, and Tiramisu Cooking Class
Small Group Pasta and Tiramisù at Local Home in Cortona

Small Group Pasta and Tiramisù at Local Home in Cortona

CA $220
per adult
Small Group Pasta and Tiramisù at Local Home in Cortona
See all activities in Cortona
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.