Cortona Old Town Vacations from ￥189,413
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The Latest Cortona Old Town Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Villa Liana
Historic Centre of Florence
￥191,562
per person
Nov 25 - Nov 27
found 21 hours ago
Roundtrip flight included
Tokyo (TYO) to Florence (FLR)
8.8/10 Excellent! (369 reviews)
My first day/night was not good. I was in a room that faced the traffic. Even with the shutters closed, it did nothing to alleviate the noise. The traffic didn't stop until midnight.
The next morning I asked if I could be moved. Thankfully a room facing the quiet courtyard was found.
Breakfast was very good, with many choices in a charming historic room.
Reviewed on Oct 14, 2026
The Moon Boutique Hotel & Spa
Historic Centre of Florence
￥208,550
per person
Nov 25 - Nov 27
found 21 hours ago
Roundtrip flight included
Tokyo (TYO) to Florence (FLR)
9.6/10 Exceptional! (605 reviews)
Even having arrived very early our room was immediately available. All staff were very helpful.
Our room was immaculately clean. The breakfast staff were outstanding very friendly and very hospitable.
The highlight though was the spa facility - out of this world.
Highly recommend The Moon Boutique.
Reviewed on Oct 16, 2026
Eurostars Florence Boutique
Historic Centre of Florence
￥195,974
per person
Nov 25 - Nov 27
found 21 hours ago
Roundtrip flight included
Tokyo (TYO) to Florence (FLR)
8.6/10 Excellent! (503 reviews)
The bed was comfortable but low to the floor. The shower was very slippery and could have used a shower mat. The breakfast was great. The staff were very nice and helpful.
Reviewed on Oct 10, 2026
Cortona Old Town Hotel Deals
Monastero di Cortona Hotel & Spa
Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
￥39,004
￥44,322 total
Oct 25 - Oct 26
includes taxes & fees
10/10 Exceptional! (353 reviews)
"Frederico went above and beyond to transfer us to our villa and Giulio was a fantastic bartender"
Reviewed on Oct 13, 2026
Hotel San Michele
Via Guelfa 15 Cortona AR
Fully refundableReserve now, pay when you stay
￥19,023
￥21,635 total
Nov 2 - Nov 3
includes taxes & fees
9/10 Wonderful! (295 reviews)
"Perfect location. Very friendly staff and spacious rooms. Right in the heart of Cortona!"
Reviewed on Oct 11, 2026
Hotel San Luca
Piazza Garibaldi 1 Cortona AR
Fully refundableReserve now, pay when you stay
￥12,820
￥15,520 total
Oct 26 - Oct 27
includes taxes & fees
8.6/10 Excellent! (448 reviews)
"Well located"
Reviewed on Oct 14, 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 ￥189,413. 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.
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.
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.
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.
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.
Museo Diocesano
7.6/10 (7 reviews)
You can browse the exhibits at Museo Diocesano, 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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.