Portole Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$2,400 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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Portole Holiday
Our pick of the best Portole Hotel Deals
Precise Tale Poggio Alla Sala
Via Poggio alla Sala 10 Montepulciano SI
Fully refundableReserve now, pay when you stay
NZ$1,103
30 Sept - 1 Oct
includes taxes & fees
9.6/10 Exceptional! (165 reviews)
"Fantastic stay!"
Reviewed on 30 Aug 2026
Villa di Piazzano - Small Luxury Hotel of the World
Localita Piazzano, C.P. 6 Cortona AR
NZ$1,198
2 Sept - 3 Sept
includes taxes & fees
9.8/10 Exceptional! (245 reviews)
"Staff was helpful , and the room was clean. The Antica Casina di Caccia dining with wine pairing was absolutely amazing. Also took some great pictures in the garden. The breakfast was nice too."
Reviewed on 17 Aug 2026
Monastero di Cortona Hotel & Spa
Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
NZ$671
13 Sept - 14 Sept
includes taxes & fees
10/10 Exceptional! (319 reviews)
"The hotel was amazing and the staff very friendly and helpful. The breakfast was spectacular. we really enjoyed ourselves at this hotel and in the city of Cortona."
Reviewed on 30 Aug 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
Tasting Tour in One of The Most Beautiful Cellars in the World
NZ$64
per adult
100% of travellers recommend
Montepulciano Wine Tasting in the Tuscan Countryside
NZ$49
per adult
Frequently asked questions
How much does a Portole holiday package cost?
You can snap up a holiday package to this top destination 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.
