Cortona Old Town Holidays

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    Save up to €900 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Price found within the past 48 hours. Click for updated prices.
  • Minibar, in-room safe, iron/ironing board, free WiFi
    Aug 14 - Aug 16

    The Hoxton Florence + Flight

    Historic Centre of Florence
    2 nights
    4.0 star property
    9.4/10 - Exceptional (274 reviews)
    "Great clean inviting hotel with amazing common spaces. Greatly appreciate it being just a smidge outside of the chaos that is the historic city center. You definitely have an extra 15-20 minute walk to get to the primary tourist destinations, but after a day of the Uffizi to Ponte Vecchio to Academia human conveyer belt, a little calming walk back to the Hoxton was a welcome and wonderful retreat. Great hotel!"
    Reviewed May 19, 2026
    Return • Dublin (DUB) - Rome (FCO)
    DUB - FCO • Direct FCO - DUB • Direct
    €474
    €375
    per traveller
    found 1 day ago
    The Hoxton Florence
  • Deluxe Double or Twin Room, Balcony, River View
    Aug 14 - Aug 16

    Hotel Balestri + Flight

    Historic Centre of Florence
    2 nights
    4.0 star property
    9.2/10 - Wonderful (1,002 reviews)
    "Nice location and room"
    Reviewed May 23, 2026
    Return • Dublin (DUB) - Rome (FCO)
    DUB - FCO • Direct FCO - DUB • Direct
    €572
    €439
    per traveller
    found 1 day ago
    Hotel Balestri
  • Terrace/patio
    Aug 14 - Aug 16

    Hotel L'Orologio Firenze + Flight

    Historic Centre of Florence
    2 nights
    4.0 star property
    9.6/10 - Exceptional (1,003 reviews)
    "Great property and great location. They have a good breakfast room at the rooftop."
    Reviewed May 25, 2026
    Return • Dublin (DUB) - Rome (FCO)
    DUB - FCO • Direct FCO - DUB • Direct
    €553
    €429
    per traveller
    found 1 day ago
    Hotel L'Orologio Firenze
  • Front of property
    Aug 14 - Aug 16

    Villa Neroli + Flight

    Coverciano
    2 nights
    4.0 star property
    9.6/10 - Exceptional (606 reviews)
    "The Villa Neroli was exceptionally clean and inviting. It caters to a little bit more upscale traveler than most of the local hotels that I could compare. Well worth the stay!!!"
    Reviewed May 21, 2026
    Return • Dublin (DUB) - Rome (FCO)
    DUB - FCO • Direct FCO - DUB • Direct
    €477
    €380
    per traveller
    found 1 day ago
    Villa Neroli
  • Lobby
    Aug 14 - Aug 16

    Hotel Garibaldi Blu + Flight

    Historic Centre of Florence
    2 nights
    4.0 star property
    9.2/10 - Wonderful (877 reviews)
    "Clean room! Staff were helpful!"
    Reviewed May 18, 2026
    Return • Dublin (DUB) - Rome (FCO)
    DUB - FCO • Direct FCO - DUB • Direct
    €489
    €392
    per traveller
    found 1 day ago
    Hotel Garibaldi Blu

Top hotels in Cortona Old Town

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 €361 per night from 8 Jun to 9 Jun
€361
8 Jun - 9 Jun
includes taxes & fees
10/10 Exceptional! (281 reviews)
"This is a fantastic hotel. Wonderful staff, an out standing fine dining restaurant, comfortable rooms and nice garden with pool. Loved it and can’t wait to go back."

Reviewed on 25 May 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 €140 per night from 21 Jun to 22 Jun
€140
21 Jun - 22 Jun
includes taxes & fees
9/10 Wonderful! (276 reviews)
"Great and helpful staff. Room was great"

Reviewed on 28 Apr 2026

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 €178 per night from 5 Jun to 6 Jun
€178
5 Jun - 6 Jun
includes taxes & fees
10/10 Exceptional! (329 reviews)
"Great hotel"

Reviewed on 13 May 2026

Hotel Villa Marsili
See all 5,000 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.

Frequently asked questions

How much does a Cortona Old Town holiday 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 holiday 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 holiday in Cortona Old Town is much closer than you thought!
Where should I stay in Cortona Old Town?
A holiday 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 Centre 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 holiday?
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 holiday!
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 holiday rentals such as beachside villas and serviced residences. The list is almost endless!
Can I choose my airline with a Cortona Old Town Expedia holiday 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 holiday 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.