Portole Holidays from AU$2,164
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Your Portole Holiday
From its highlights to its hidden gems, this city is best explored with a Portole holiday package. Check out places to stay in Contrada Castello, which is great for dining, views and culture. You'll want to take in some sights during your trip to Portole. Swing by top attractions such as Villa Bramasole, Cathedral of Cortona and Piazza della Repubblica. Stop dreaming and start adventuring. Check out the wide range of options on Expedia today and put your Portole holiday plans in motion!
The Latest Portole Holiday Deals
Price found within the past 48 hours. Click for updated prices.
La Monastica Resort & Spa
AU$2,952
per person
4 Dec - 8 Dec
found 1 day ago
Return direct flight included
Sydney (SYD) to Florence (FLR)
10/10 Exceptional! (39 reviews)
Beautiful property with great and helpful staff. Everything was excellent but it’s missing an outdoor bar and the gym is extremely poor
Reviewed on 22 Aug 2026
Excelsior Palace Portofino Coast
AU$2,555
per person
4 Dec - 8 Dec
found 1 day ago
Return direct flight included
Sydney (SYD) to Pisa (PSA)
9.4/10 Exceptional! (1,002 reviews)
It’s a nice hotel. They have a solo music player in the evening. I’ll expect a higher quality breakfast from a 5 * hotel but all in all is a great hotel.
Reviewed on 7 Sept 2026
Portole Holiday
Portole Essential Information
Language | Italian |
|---|---|
Currency | Euros |
Local Welcome | Ciao |
Local Goodbye | Ciao |
Closest Airport | Sant Egidio Airport (PEG) |
Max Temp Winter | 7ºC |
Max Temp Summer | 27ºC |
Top Sights | Cathedral of Cortona, Signorelli Theatre and Palazzo Comunale |
Our pick of the best Portole Hotel Deals
Villa di Piazzano - Small Luxury Hotel of the World
Localita Piazzano, C.P. 6 Cortona AR
AU$1,015
10 Oct - 11 Oct
includes taxes & fees
9.8/10 Exceptional! (247 reviews)
"Such a fantastic property, the most amazing food and great surroundings. Just a thoroughly lovely experience."
Reviewed on 3 Sept 2026
Precise Tale Poggio Alla Sala
Via Poggio alla Sala 10 Montepulciano SI
Fully refundableReserve now, pay when you stay
AU$786
30 Sept - 1 Oct
includes taxes & fees
9.6/10 Exceptional! (167 reviews)
"Incredible stay in a beautiful location. The staff were amazing and the hospitality was top tier. We will most definitely be back. The recommendations given were brilliant and the room was stunning along with the rest of the hotel. We didn’t dine in the restaurant but our breakfast each morning was ..."
Reviewed on 5 Sept 2026
Monastero di Cortona Hotel & Spa
Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
AU$568
27 Sept - 28 Sept
includes taxes & fees
10/10 Exceptional! (327 reviews)
"Amazing ."
Reviewed on 8 Sept 2026
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.
What to do in Portole
Montepulciano Wine Tasting in the Tuscan Countryside
AU$41
per adult
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
AU$137
per adult
98% of travellers recommend
Montepulciano: Winery Tour and Tasting
AU$57
per adult
100% of travellers recommend
Frequently asked questions
How much does a Portole holiday package cost?
You can snap up a holiday package to this top destination from AU$2,164 on Expedia. However, how much your holiday to Portole costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Portole?
If you'd like to book a cheap Portole holiday package, consider travelling in January, February and March. You'll usually find lower rates on flights and accommodation during these quieter months — ideal for budget-conscious travellers.
How many days is enough for Portole?
Usually, a handful of days is enough to check out the major attractions during your Portole holiday. However, if you want to have time to rest or take day trips, think about extending your trip.
How to find the best Portole package deals?
Begin your search for a Portole package deal by entering your destination and travel dates under our "Packages" tab. Then add a few filters, like "Guest rating" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Portole package deal right away, just switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Portole escape off to a flying start.
Is it cheaper to book a Portole holiday as a package?
An Expedia holiday package could land you significant savings when compared to booking flights and hotels separately. Better still, you can customise your Portole getaway to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a holiday package to Portole?
If you have your Portole holiday dates finalized, book early to bag some outstanding deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are great for travelling on a whim.
How to plan a trip to Portole?
- Pick the right time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to travel to Portole.
- Plan your budget wisely: In addition to the cost of your hotel, you'll need to factor in other expenses too. These include food, transportation and flights. Also, put aside a little extra for unexpected expenses that may crop up during your trip to Portole.
- Work out your trip length: Think about how long you want to spend discovering Portole. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a comfortable pace.
- Bundle your airfare and accommodation: After you've settled on your dates and duration, book the right Portole 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.
