Cortona Old Town Holidays

Photo by Dominik Majewski

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Price found within the past 48 hours. Click for updated prices.
Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Price was S$1,410, price is now S$1,132 per person
S$1,132
per person
14 Feb - 17 Feb
found 7 hours ago
Return flight included
Singapore (SIN) to Florence (FLR)
7.6/10 Good! (1,002 reviews)
The room was okay. For the price can’t ask for better. Everything work fine, fully equipped, and breakfast included with very good choices of items and coffees. I will return to this place if I have another opportunity because the staff it’s very friendly, very close to the train station and with lots of restaurants and stores around.

Reviewed on 15 Dec, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was S$1,456, price is now S$1,150 per person
S$1,150
per person
14 Feb - 17 Feb
found 7 hours ago
Return flight included
Singapore (SIN) to Florence (FLR)
7.8/10 Good! (1,000 reviews)
Great Locations walkable to all the placese.

Reviewed on 15 Dec, 2025

Hotel Duomo Firenze

Hotel Duomo Firenze

3 out of 5
Historic Centre of Florence
Price was S$1,605, price is now S$1,348 per person
S$1,348
per person
14 Feb - 17 Feb
found 7 hours ago
Return flight included
Singapore (SIN) to Florence (FLR)
9.2/10 Wonderful! (1,002 reviews)
The breakfast was great, I don't drink but they have a pig leg and wine for breakfast that stood out. Free gelato all day long. Location spectacular. Only downside is small rooms (you are in Florence normal) and water pressure and temp was a struggle

Reviewed on 22 Dec, 2025

Hotel degli Orafi

Hotel degli Orafi

4 out of 5
Historic Centre of Florence
Price was S$1,600, price is now S$1,384 per person
S$1,384
per person
14 Feb - 17 Feb
found 7 hours ago
Return flight included
Singapore (SIN) to Florence (FLR)
9.6/10 Exceptional! (1,001 reviews)
Spacious room much bigger than an average single.

Reviewed on 27 Nov, 2025

Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

4 out of 5
Historic Centre of Florence
Price was S$1,439, price is now S$1,252 per person
S$1,252
per person
14 Feb - 17 Feb
found 7 hours ago
Return flight included
Singapore (SIN) to Florence (FLR)
8.8/10 Excellent! (939 reviews)
The room is very nice , clean & spacios. The elevator is too small, good for 2 persons only. If you have luggage, only 1 person. You still have to use stairs before you reach your room even you use the elevator. The breakfast is good. The staff are friendly.

Reviewed on 19 Dec, 2025

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 S$435 per night from 4 Jan to 5 Jan
S$435
4 Jan - 5 Jan, 2026
includes taxes & fees
9.8/10 Exceptional! (255 reviews)
Everything was perfect! Would like to give this Property a 6 Star rating. The staff made you feel like royalty!!

Reviewed on 18 Dec, 2025

Monastero di Cortona Hotel & Spa
Hotel San Michele

Hotel San Michele

4 out of 5
Via Guelfa 15 Cortona AR
9/10 Wonderful! (270 reviews)
Very friendly and helpful staff. Nice rooms

Reviewed on 7 Sept, 2025

Get rates
Hotel San Michele
Hotel Italia

Hotel Italia

3 out of 5
Via Ghibellina 5/7 Cortona AR
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (279 reviews)
The hotel amenities, comfort, hospitality are top notch. Should easily be a 4-star hotel!

Reviewed on 7 Dec, 2025

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Hotel Italia
See all 4,965 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 S$1,132. 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.

Popular places to visit

Palazzo Comunale

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 theatre.

Palazzo Comunale

Things to do

Tuscany: Sanctuary of La Verna Day Tour Private Tour

Tuscany: Sanctuary of La Verna Day Tour Private Tour

S$711
per traveller
Tuscany: Sanctuary of La Verna Day Tour Private Tour
Traditional Tuscan Cuisine Cooking Class, Castiglion Fiorentino near Cortona

Traditional Tuscan Cuisine Cooking Class, Castiglion Fiorentino near Cortona

S$205
per adult
Traditional Tuscan Cuisine Cooking Class, Castiglion Fiorentino near Cortona
For your personal cooking class in Tuscany

Amazing four courses cooking class in Tuscany

S$332
per adult
Amazing four courses cooking class in Tuscany
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.