Cortona Old Town Vacation Packages
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Top Holiday Package Deals in Cortona Old Town
Price found within the past 48 hours. Click for updated prices.
Hotel degli Orafi
Historic Centre of Florence
CA $1,726
per person
Nov 13 - Nov 19
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9.6/10 Exceptional! (1,005 reviews)
Absolutely everything about our stay was lovely. Service, breakfast, beds, air conditioning, quiet rooms, all staff members, location, roof top bar. Cannot say enough about how much we liked it here!
Reviewed on Oct 4, 2026
The Moon Boutique Hotel & Spa
Historic Centre of Florence
CA $2,001
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9.6/10 Exceptional! (600 reviews)
Extremely clean, breakfast service was awesome. Absolutely beautiful room . Shower with steam and jacuzzi settings was wonderful.
Reviewed on Oct 2, 2026
Monastero di Cortona Hotel & Spa
Cortona Old Town
CA $2,729
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
10/10 Exceptional! (337 reviews)
5 star treatment, indoor pool is a charge to use and parking is rough. Overall excellent experience. Staff is great.
Reviewed on Oct 4, 2026
Glance Hotel In Florence
Historic Centre of Florence
CA $2,347
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.4/10 Exceptional! (1,001 reviews)
Florence is a walkable city for most (uneven surfaces) making this a great location. It’s a 7 - 10 minute walk (depending on luggage) from the train station.
Great rooftop pool with great views and service. The Club sandwich is among the best we have ever had. Sunset in the pool was amazing too.
Breakfast was exceptional with great selection and great coffee !
Reviewed on Sep 28, 2026
Cortona Old Town Hotel Deals
Monastero di Cortona Hotel & Spa
Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
CA $357
CA $405 total
Oct 25 - Oct 26
includes taxes & fees
10/10 Exceptional! (343 reviews)
"5 star treatment, indoor pool is a charge to use and parking is rough. Overall excellent experience. Staff is great."
Reviewed on Oct 4, 2026
Hotel San Michele
Via Guelfa 15 Cortona AR
Fully refundableReserve now, pay when you stay
CA $184
CA $209 total
Nov 4 - Nov 5
includes taxes & fees
Hotel San Luca
Piazza Garibaldi 1 Cortona AR
Fully refundableReserve now, pay when you stay
CA $116
CA $140 total
Oct 28 - Oct 29
includes taxes & fees
8.6/10 Excellent! (444 reviews)
"très bien situé, lit un peu trop dur"
Reviewed on Sep 26, 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.
Frequently asked questions
How much does a Cortona Old Town vacation package cost?
From as little as CA $1,726. 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.
Stay near popular Cortona Old Town attractions
Piazza della Repubblica
9.4/10 (95 reviews)
Find out about the history of Cortona with a stop at Piazza della Repubblica. Make time to visit the cathedral and monuments while you're in the area.
Cortona Cathedral
9.4/10 (77 reviews)
Cortona Cathedral is just one of the places to see in Cortona, so why not enjoy the other things to explore during your travels? Experience the area's museums and musical theater.
Fortress of Girifalco
8.8/10 (25 reviews)
You can find out about the history of Cortona when you stop by Fortress of Girifalco. You can enjoy the wineries while in the area.
Santa Margherita Basilica
9.2/10 (30 reviews)
You can learn about the history of Cortona when you stop by Santa Margherita Basilica. Discover the area's museums and cathedral.
San Domenico Church
9.0/10 (9 reviews)
After visiting San Domenico Church, make a plan to see the other sights and activities in Cortona. Make time to visit the cathedral and monuments while you're in the area.
Palazzo Comunale
9.2/10 (44 reviews)
Palazzo Comunale is just one of the places to see in Cortona, so why not enjoy the other things to explore during your travels? Experience the area's museums and musical theater.
Museum of the Etruscan Academy
8.8/10 (18 reviews)
You can browse the exhibits at Museum of the Etruscan Academy, a museum with a storied past, during your trip to Cortona. Experience the area's museums and musical theater.
Signorelli Theatre
9.2/10 (14 reviews)
You can make plans for a show at Signorelli Theatre during your stay in Cortona. Discover the area's countryside and monuments.
Things to do
Pasta or Pizza cooking class in Cortona, vegetarian and vegan
CA $193
per adult
Tuscan Cooking Classes in Cortona Pizza Focaccia and Calzoni
CA $196
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.