Cortona Old Town Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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Price found within the past 48 hours. Click for updated prices.
  • Quadruple Room
    Jul 20 - Jul 28

    Aurum Firenze + Flight

    Historic Centre of Florence
    7 nights
    4.0 star property
    7.6/10 - Good (1,023 reviews)
    "Très bien situé, tout près du centre. Terrasse pour le déjeuner très agréable! Chambre bien aménagée et pratique."
    Reviewed June 5, 2026
    Roundtrip • Montreal (YUL) - Florence (FLR)
    YUL - FLR • 1 stop FLR - YUL • 1 stop
    CA $2,604
    CA $1,463
    per traveller
    found 18 hours ago
    Aurum Firenze
  • Triple Room | Bathroom
    Jul 22 - Aug 2

    Aurum Uffizi + Flight

    Historic Centre of Florence
    10 nights
    4.0 star property
    7.6/10 - Good (1,012 reviews)
    "The hotel was conveniently located, and the service was good. Overall, it was a pleasant stay. However, I hope the hotel improves its Wi-Fi coverage, as the connection can become unstable when multiple guests are accessing the network."
    Reviewed June 5, 2026
    Roundtrip • Montreal (YUL) - Florence (FLR)
    YUL - FLR • 1 stop FLR - YUL • 1 stop
    CA $3,459
    CA $1,866
    per traveller
    found 23 hours ago
    Aurum Uffizi
  • Exterior
    Aug 20 - Aug 30

    Precise Tale Poggio Alla Sala + Flight

    Montepulciano
    9 nights
    5.0 star property
    9.6/10 - Exceptional (143 reviews)
    "It was a beautiful hotel with the most wonderful views. The staff was absolutely phenomenal. And I would highly recommend this to anyone looking to stay in Tuscany."
    Reviewed June 7, 2026
    Roundtrip • Toronto (YYZ) - Rome (FCO)
    YYZ - FCO • 1 stop FCO - YYZ • 1 stop
    CA $9,868
    CA $5,519
    per traveller
    found 21 hours ago
    Precise Tale Poggio Alla Sala
  • Rooftop terrace
    Jul 22 - Aug 2

    Donati Luxury Tower Suites + Flight

    Historic Centre of Florence
    10 nights
    5.0 star property
    9.8/10 - Exceptional (66 reviews)
    "Agradable estancia. Excelente servicio. La habitación la mantenían siempre limpia. Todo queda cerca del área. Muy recomendable"
    Reviewed May 23, 2026
    Roundtrip • Montreal (YUL) - Florence (FLR)
    YUL - FLR • 1 stop FLR - YUL • 1 stop
    CA $8,852
    CA $5,742
    per traveller
    found 23 hours ago
    Donati Luxury Tower Suites
  • Breakfast area
    Jul 22 - Aug 2

    The Moon Boutique Hotel & Spa + Flight

    Historic Centre of Florence
    10 nights
    4.0 star property
    9.6/10 - Exceptional (566 reviews)
    "Absolutely fantastic hotel, we couldn’t believe how good it was. Exactly like the photos. The hotel was built only in 2018 and the facilities are constantly kept in perfect condition and spotlessly clean. In a quiet part of town easily walkable into the main attractions and close to a bus and a tram stop, a perfect sanctuary to rest at night time. All of the staff are so kind and polite, especially Francois who looked after us very well at breakfast time. The hotel would be worth the price tag..."
    Reviewed June 8, 2026
    Roundtrip • Montreal (YUL) - Florence (FLR)
    YUL - FLR • 1 stop FLR - YUL • 1 stop
    CA $3,916
    CA $2,582
    per traveller
    found 23 hours ago
    The Moon Boutique Hotel & Spa

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 $579 per night from Jul 5 to Jul 6
CA $579
CA $650 total
Jul 5 - Jul 6
includes taxes & fees
10/10 Exceptional! (284 reviews)
"Incredible hotel! Beautiful location. Excellent food. Comfortable beds and bedrooms. Lovely little bar, excellent spa. You have to stay here and treat yourself!"

Reviewed on Jun 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 $195 per night from Jun 23 to Jun 24
CA $195
CA $228 total
Jun 23 - Jun 24
includes taxes & fees
9/10 Wonderful! (279 reviews)
"The location is fantastic. Just steps from the shopping and restaurants. The hotel is old fashioned and charming. The bathrooms are in need of an upgrade both fixtures and lighting. But it’s quirky ways also are the very thing that makes it charming. I would ask for a room furthest away from Via ..."

Reviewed on Jun 3, 2026

Hotel San Michele
Hotel San Luca

Hotel San Luca

4 out of 5
Piazza Garibaldi 1 Cortona AR
Fully refundableReserve now, pay when you stay
The price is CA $122 per night from Jun 22 to Jun 23
CA $122
CA $147 total
Jun 22 - Jun 23
includes taxes & fees
8.6/10 Excellent! (428 reviews)
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Reviewed on May 29, 2026

Hotel San Luca
See all 5,049 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 . 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 $193
per adult
Pasta or Pizza cooking class in Cortona, vegetarian and vegan
PIZZA

Tuscan Cooking Classes in Cortona Pizza Focaccia and Calzoni

CA $196
per adult
Tuscan Cooking Classes in Cortona Pizza Focaccia and Calzoni
NOODLES

Authentic Tuscan Cooking Classes in Cortona-Pasta and Tiramisu'

CA $177
per adult
Authentic Tuscan Cooking Classes in Cortona-Pasta and Tiramisu'
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.