Cortona Holidays

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Cortona Holiday

Our pick of the best Cortona Hotel Deals

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 NZ$994 per night from 20 Aug to 21 Aug
NZ$994
20 Aug - 21 Aug
includes taxes & fees
9.6/10 Exceptional! (218 reviews)
"AMAZING! Gorgeous! I would recommend to everyone!"

Reviewed on 29 Jul. 2025

Villa di Piazzano - Small Luxury Hotel of the World
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 NZ$624 per night from 17 Aug to 18 Aug
NZ$624
17 Aug - 18 Aug
includes taxes & fees
9.8/10 Exceptional! (225 reviews)
"Gorgeous hotel, very helpful and friendly staff, stunning pool and spa. Loved everything about this hotel! Just know that it’s an uphill walk to get there from the town center."

Reviewed on 22 Jul. 2025

Monastero di Cortona Hotel & Spa
Il Falconiere - Relais e Chateaux

Il Falconiere - Relais e Chateaux

5 out of 5
Localita San Martino 370, Cortona, AR
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (110 reviews)
"Perfect stay! Couldn’t recommend more highly"

Reviewed on 8 Jul. 2025

Get rates
Il Falconiere - Relais e Chateaux
See all 1,306 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.

Discover the most popular places to visit in Cortona

Villa Bramasole

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

Villa Bramasole

Casali Palace

4/5(1 review)

You can study the exhibits at Casali Palace, a museum with a storied past, during your travels to Cortona. Make time to visit the cathedral and monuments while you're in the area.

Casali Palace

What to do in Cortona

Bottaia

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

NZ$64
per adult
100% of travellers recommend
Tasting Tour in One of The Most Beautiful Cellars in the World
Montepulciano Wine Tasting in the Tuscan Countryside

Montepulciano Wine Tasting in the Tuscan Countryside

NZ$49
per adult
Montepulciano Wine Tasting in the Tuscan Countryside
Oil museum and oil mill in Tuscany: tour and tasting

Oil museum and oil mill in Tuscany: tour and tasting

NZ$39
per adult
Oil museum and oil mill in Tuscany: tour and tasting
See all activities in Cortona

Frequently asked questions

How much does a Cortona holiday package cost?
You'll find cheap prices on Expedia for your Cortona break. However, factors like the season, length of stay and your choice of hotel will influence how much your holiday to Cortona costs.
What are the cheapest months to go to Cortona?
If you'd like to snag a cheap Cortona holiday package, consider travelling in December, January and February. You're likely to find better prices on airfares and hotels during these months — perfect for travellers wishing to save money.
How many days is enough for Cortona?
With around 3 days, you'll have enough time to enjoy popular neighbourhoods like Cortona Old Town and Sodo during your Cortona holiday. Be sure to also add Palazzo Comunale and Museum of the Etruscan Academy to your must-see list. Searching for more adventures? Consider exploring outside of Cortona on tours and day trips.
Is it worth booking a holiday package to Cortona?
Popular for its views, dining and walking trails, a Cortona holiday is a hit with all kinds of visitors. Be sure to check out top sights like Villa Bramasole and Piazza della Repubblica, and consider renting a set of wheels for day trips to discover even more.
How to find the best Cortona package deals?
Start your search for a Cortona package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply a few filters, like "Property type" and "Popular locations," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Cortona package deal straight away, simply switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Cortona escape underway.
Is it cheaper to book a Cortona holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to arranging flights and stays individually. Better still, you can customise your Cortona trip to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a holiday package to Cortona?
If you're considering an impromptu Cortona holiday, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can land terrific deals on your flights and hotels by booking well in advance.
How to plan a trip to Cortona?

  1. Choose when to go: Check your calendar and get packing. Your favourite season and the type of activities available will also help you decide when to escape to Cortona.
  2. Budget wisely: Besides the price of your stay, you'll need to factor in other expenses too. These include food, transportation and flights. Also, set aside some extra funds for unexpected costs that could crop up during your trip to Cortona.
  3. Work out your trip length: Think about how much time you'd like to spend discovering Cortona. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Bundle your accommodation and airfare: Once you've nailed down your dates and duration, book the right Cortona holiday package for you.

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