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.
Grand Hotel Cavour
Historic Centre of Florence
CA $4,785
per person
Sep 25 - Sep 29
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Florence (FLR)
9.2/10 Wonderful! (1,001 reviews)
Staff were very welcoming and helpful from check in to departure. We had the basic room which was very nice indeed, a decent size and nicely furnished. Rooftop bar reasonable value for a cocktail surrounded by the sights of Florence. Very central location. Aircon very good and controllable. Highly recommended.
Reviewed on Aug 19, 2026
The Poet Hotel
La Spezia Historic Centre
CA $1,789
per person
Oct 2 - Oct 8
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Pisa (PSA)
9.2/10 Wonderful! (1,002 reviews)
The hotel lobby vibe is very energetic and positive. The staffs are amazing and helpful. My room is on the first floor with no lift access and they help us to bring up to our room and carry it down for check out. I had an injury of my wrist and needed ice compression and they were very kind to give me the ice pack for free. However, room is slightly cramped for 2 30” luggages
Reviewed on Aug 12, 2026
Cortona Old Town Hotel Deals
Monastero di Cortona Hotel & Spa
Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
CA $420
CA $475 total
Aug 30 - Aug 31
includes taxes & fees
10/10 Exceptional! (310 reviews)
"We stayed at Monestero di Cortona for six nights, and it felt like the perfect amount of time. The hotel is beautiful, and the service and hospitality teams were incredibly friendly, attentive, and always willing to help or go the extra mile. We also enjoyed the spa services, which were fantastic! ..."
Reviewed on Aug 17, 2026
Hotel San Luca
Piazza Garibaldi 1 Cortona AR
Fully refundableReserve now, pay when you stay
CA $140
CA $167 total
Aug 28 - Aug 29
includes taxes & fees
8.6/10 Excellent! (437 reviews)
"Wonderful place to stay in Cortona Great breakfast"
Reviewed on Jul 23, 2026
Hotel San Michele
Via Guelfa 15 Cortona AR
Fully refundableReserve now, pay when you stay
CA $194
CA $226 total
Aug 20 - Aug 21
includes taxes & fees
9.2/10 Wonderful! (287 reviews)
"The hotel is very centrally located The room are spacious and very clean The staff is efficient and helpful The breakfast could be better and the premises in general need refurbishment"
Reviewed on Aug 16, 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 $1,475. 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
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.
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.
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.
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.
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.
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.
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.
Casali Palace
8.6/10 (7 reviews)
You can study the exhibits at Casali Palace, a museum with a storied past, during your trip to Cortona. Make time to visit the cathedral and monuments while you're in the area.
Things to do
Lake Trasimeno: Stand-Up Paddleboard Lesson
CA $48
per adult
Pasta or Pizza cooking class in Cortona, vegetarian and vegan
CA $193
per adult
Tuscan Cooking Classes in Cortona Pizza Focaccia and Calzoni
CA $197
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.