Cortona Vacations from $1,088

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Your Cortona Vacation

When a city getaway is calling, answer it with a Cortona vacation package. The neighborhood of Contrada Castello, which is good for dining, views and culture, makes a wonderful base for your adventures. A trip to Cortona is a great opportunity to go sightseeing. Check out well-known attractions like Villa Bramasole, Piazza della Repubblica and Signorelli Theatre. Stop daydreaming and start doing. Explore the many options on Expedia today and put your Cortona vacation plans into gear!

The Latest Cortona Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Santa Maria Novella
per person
Jul 20 - Jul 25
found 1 day ago
Roundtrip non-stop flight included
Newark (EWR) to Florence (FLR)
9.6/10 Exceptional! (370 reviews)
Our booking stated we would receive spa access, 1 Free spa service for 2 (we had the room booked for two people), free breakfast, etc. While we received most of this and it was fantastic, the one VIP benefit we looked forward to the most (spa service for 2) we did not get. We were told twice by the hotel staff that this was “an error from Expedia”. I’m not sure why but this took a fantastic stay down to average as it should have been honored, especially when we showed them the booking details tagged to the VIP access we paid for in advance.

Reviewed on Jun 8, 2024

Plaza Hotel Lucchesi

Plaza Hotel Lucchesi

4 out of 5
Santa Croce
Save 100% on your flight
per person
Jul 23 - Jul 30
found 1 day ago
Roundtrip non-stop flight included
Newark (EWR) to Florence (FLR)
9.4/10 Exceptional! (1,000 reviews)
Highly recommend, perfect location and amazing staff

Reviewed on Jun 4, 2024

Hotel L'Orologio

Hotel L'Orologio

4 out of 5
Santa Maria Novella
per person
Jul 23 - Jul 30
found 1 day ago
Roundtrip non-stop flight included
Newark (EWR) to Florence (FLR)
9.4/10 Exceptional! (979 reviews)
Nice hotel But very overpriced Bad breakfast Not very nice customer service Will not stay there again Very good location though

Reviewed on Jun 2, 2024

Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

3 out of 5
Oltrarno
per person
Aug 18 - Aug 23
found 11 hours ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
8.6/10 Excellent! (622 reviews)
We stayed for one night and we really like this hotel. Staff were friendly, hotel was super clean and room was spacious.

Reviewed on Jun 8, 2024

Aurum Uffizi

Aurum Uffizi

4 out of 5
Santa Croce
per person
Aug 18 - Aug 23
found 11 hours ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
8/10 Very Good! (890 reviews)
Great location and staff. The property was very clean. The only gripe I have is the bed is super hard (and I like a firm mattress). The pillows also left much to be desired but the staff happily gave us extra. Overall, a great value. Even with the bed, I’d probably stay here again as the location makes up for everything.

Reviewed on Jun 5, 2024

Cortona Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Population
2,200
Max Temp Winter
45ºF
Max Temp Summer
80ºF
Top Sights
Signorelli Theatre, Cathedral of Cortona and San Luciano Winery

Cortona Hotel Deals

Monastero di Cortona Hotel & Spa
Monastero di Cortona Hotel & Spa
5 out of 5
Via del Salvatore, Cortona
Fully refundableReserve now, pay when you stay
The price is $287 per night from Jun 23 to Jun 24
$287
$325 total
includes taxes & fees
Jun 23 - Jun 24
9.8/10 Exceptional! (171 reviews)
"An idyllic place to stay in an idyllic town. Everything thing about the hotel is very calming. Absolutely loved it."

Reviewed on Jun 7, 2024

Monastero di Cortona Hotel & Spa
Villa di Piazzano - Small Luxury Hotel of the World
Villa di Piazzano - Small Luxury Hotel of the World
5 out of 5
Localita Piazzano, C.P. 6, Cortona, AR
The price is $501 per night from Jun 16 to Jun 17
$501
$560 total
includes taxes & fees
Jun 16 - Jun 17
9.6/10 Exceptional! (176 reviews)
Amazing property, service and food!
"This hotel is one of the best we have experienced. The setting is beautiful, the room was very nice, the food was the best we had in Italy (and beyond) and the service is impeccable. The entire staff is amazing, but we wanted to point out the extra efforts from Paolo, Davide and Mikelo. Now we know ..."

Reviewed on May 27, 2024

Villa di Piazzano - Small Luxury Hotel of the World
Borgo Il Melone
Borgo Il Melone
4 out of 5
Case Sparse, 38, Localita Il Sodo, Cortona, AR
Fully refundableReserve now, pay when you stay
The price is $97 per night from Jun 21 to Jun 22
$97
$116 total
includes taxes & fees
Jun 21 - Jun 22
8.6/10 Excellent! (233 reviews)
"All around excellence. Great location. Clean and spacious."

Reviewed on May 19, 2024

Borgo Il Melone
See all 1,304 properties in Cortona
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.

All Inclusive Vacations

All Inclusive Vacations

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Frequently asked questions

How much does a Cortona vacation package cost?
Less than you might think — from just $1,088, as a matter of fact! By bundling flights, hotels and car rentals into a tailor-made package, your Cortona escape is just a few clicks away.
How do I get a cheap travel package to Cortona?
Bundling your flight and hotel with Expedia won’t just save you time — it’ll save you cash too. A Cortona vacation package makes it easy to put together the ideal trip. With more than 550 airlines worldwide to select from, finding convenient flights that fit your busy schedule won’t be a hassle. On top of that, we have over 1,000,000 hotels globally to choose from. Now that’s what you call choice. Whatever your budget, Expedia puts the world within your reach.
Where should I stay in Cortona?
With so much to discover in Cortona, we suggest you secure a room in a hotel near its attractions. Villa Bramasole, Piazza della Repubblica and Cathedral of Cortona are some fascinating ones to add to your to-do list.
What are the top hotels in Cortona?
Travelers journeying to Cortona often book a room at Monastero di Cortona Hotel & Spa or Villa di Piazzano - Small Luxury Hotel of the World. You’ll find them in Cortona Old Town. Another interesting neighborhood is Fratticciola. Hotel San Michele and Borgo Il Melone are popular options in this area.
How far in advance should I book my Cortona vacation?
Search Expedia to compare airfares as soon as possible. You can normally purchase a seat up to 12 months before departure. If it’s too early for your preferred carrier, or you’re booking late, don’t worry. Cheap fares to Cortona occasionally appear a few weeks before departure.
What does an Expedia Cortona travel package include?
Expedia has all you need to book your Cortona trip, but how your package is structured is entirely up to you. Choose from a combination of hotels, rental cars and flights. Looking for a few activities to keep you on the go? Once you’ve made your booking, you can add them on too. No matter your budget, there’s a vacation package to match your needs.
What should I know before booking a Cortona travel package?
Whether it’s adventure or relaxation you’re after, a Cortona vacation package lets you plan your escape your way. Plus, you’ll get access to great discounts just for combining your hotel with your rental car and flights. The more you bundle, the more you’ll save!
Can I choose my airline with a Cortona Expedia vacation package?
You can. We have more than 550 partner airlines across the globe, so select the carrier that suits your budget and traveling style.
If I'm not able to travel, can I cancel my Cortona vacation package?
Whether it’s your flight or hotel, you can cancel or amend it. Booked your Cortona vacation package in the last 24 hours? You may be able to make changes or cancellations for free. For bookings older than that, you may incur a fee from your airline, hotel or car rental company. For further information, browse our Customer Service Portal. We’ll help you every step of the way.

Discover the most popular places to visit in Cortona

Image for Piazza della Repubblica

Piazza della Repubblica

5/5(4 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.

Piazza della Repubblica
Image for Villa Bramasole

Villa Bramasole

You can learn about the history of Cortona with a trip to Villa Bramasole. You can enjoy the wineries while in the area.

Villa Bramasole
Image for Cathedral of Cortona

Cathedral of Cortona

Find out about the history of Cortona with a stop at Cathedral of Cortona. Make time to visit the cathedral and monuments while you're in the area.

Cathedral of Cortona

What to do in Cortona

Image for Tuscany: Sanctuary of La Verna Day Tour Private Tour

Tuscany: Sanctuary of La Verna Day Tour Private Tour

$487
Per adult
Tuscany: Sanctuary of La Verna Day Tour Private Tour
Image for Tasting Tour in One of The Most Beautiful Cellars in the World

Tasting Tour in One of The Most Beautiful Cellars in the World

$30
Per adult
100% of travellers recommend
Tasting Tour in One of The Most Beautiful Cellars in the World
Image for Val D'Orcia: Montepulciano, Pienza, Montalcino with Winery

Val D'Orcia: Montepulciano, Pienza, Montalcino with Winery

$759
Per adult
Val D'Orcia: Montepulciano, Pienza, Montalcino with Winery
See all activities in Cortona

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.