Cortona Old Town Holidays

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    Save up to S$1,300 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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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
The price is S$347 per night from 29 Nov to 30 Nov
S$347
29 Nov - 30 Nov
includes taxes & fees
9.8/10 Exceptional! (366 reviews)
"The highlight was the experience at the bar with the entertaining bartenders! Great breakfast and service!"

Reviewed on 2 Nov, 2026

Monastero di Cortona Hotel & Spa
Hotel San Luca

Hotel San Luca

4 out of 5
Piazza Garibaldi 1 Cortona AR
8.6/10 Excellent! (449 reviews)
"Well located"

Reviewed on 14 Oct, 2026

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Hotel San Luca
Hotel San Michele

Hotel San Michele

4 out of 5
Via Guelfa 15 Cortona AR
9/10 Wonderful! (296 reviews)
"Great location"

Reviewed on 1 Nov, 2026

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Hotel San Michele
See all 4,939 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.

Stay near popular Cortona Old Town attractions

Piazza della Repubblica

9.4/10 (95 reviews)
Find out about the history of Cortona when you take a trip to Piazza della Repubblica. Make time to visit the cathedral and monuments while you're in the area.
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Things to do

Foiano della Chiana: Chianina and Cinta Senese Farm Tour

Foiano della Chiana: Chianina and Cinta Senese Farm Tour

S$50
per adult
Foiano della Chiana: Chianina and Cinta Senese Farm Tour
Montepulciano: Wine Tour and tasting

Montepulciano: Wine Tour and tasting

S$75
per traveller
Montepulciano: Wine Tour and tasting
Montalcino: Wine Tasting and Tuscan Lunch

Montalcino: Wine Tasting and Tuscan Lunch

S$85
per adult
Montalcino: Wine Tasting and Tuscan Lunch
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.