Portole Vacations from $1,189
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Your Portole Vacation
Lock in a Portole vacation package and get set to experience the best of this lively city. Think about staying in the neighborhood of Contrada Castello, which is great for dining, views and culture. Make your trip to Portole even more enjoyable by including some sightseeing. Villa Bramasole, Piazza della Repubblica and Cathedral of Cortona are among the popular attractions worth exploring. Stop dreaming and start doing. Browse the wide range of options on Expedia today and put your Portole vacation plans into motion!
The Latest Portole vacation packages
Price found within the past 48 hours. Click for updated prices.
Aurum Firenze
Historic Centre of Florence
$1,233
per person
Oct 21 - Oct 27
found 6 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,003 reviews)
Brilliant location, no more than 15-20 maximum minutes to walk to all the main sites. The staff worked hard and were very friendly and helpful.
Reviewed on Sep 17, 2026
Grand Hotel Cavour
Historic Centre of Florence
$2,465
per person
Nov 4 - Nov 9
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.2/10 Wonderful! (1,004 reviews)
Lovely hotel and great position in Florence. Staff were friendly and helpful. Breakfast was lovely plenty of choice. Wouldn’t hesitate to stay there again. Perfect for the usual sightseeing !
Reviewed on Sep 15, 2026
What to do in Portole
Montepulciano Wine Tasting in the Tuscan Countryside
$29
per adult
Montepulciano: Winery Tour and Tasting
$41
per adult
100% of travellers recommend
Horseback riding through the vineyards in Montepulciano Tuscany
$93
per adult
Portole Hotel Deals
Villa di Piazzano - Small Luxury Hotel of the World
Localita Piazzano, C.P. 6 Cortona AR
$635 nightly
$708 total
Oct 19 - Oct 20
Total with taxes and fees
Monastero di Cortona Hotel & Spa
Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
$361 nightly
$406 total
Oct 11 - Oct 12
Total with taxes and fees
10/10 Exceptional! (335 reviews)
"There was nothing to be improved because everything was perfection!!"
Reviewed on Sep 19, 2026
Nuovo Etruria Resort
Via di S. Martino snc Montepulciano SI
Fully refundable
$113 nightly
$129 total
Oct 21 - Oct 22
Total with taxes and fees
9.2/10 Wonderful! (129 reviews)
"All good"
Reviewed on Sep 15, 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.
Find the Best Portole Vacation Packages
Portole Essential Information
Language | Italian |
|---|---|
Currency | Euros |
Local Welcome | Ciao |
Local Goodbye | Ciao |
Closest Airport | Sant Egidio Airport (PEG) |
Top Sights | Signorelli Theatre, Cathedral of Cortona and Museum of the Etruscan Academy |
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Frequently asked questions
How much does a Portole vacation package cost?
You can snap up a vacation package to this top destination from $1,189 on Expedia. However, how much your vacation 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?
You can generally find reduced prices and greater availability in October, November and December. Browse our cheap Portole vacation packages and you could land some great off-season deals.
How many days is enough for Portole?
The ideal length of your Portole vacation depends on what you'd like to do. Generally, a few days to a week will give you plenty of time to visit all the main sights and explore some hidden treasures along the way.
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 vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking flights and hotels separately. Better still, you can customize 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 vacation package to Portole?
If you have your Portole vacation 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 traveling on a whim.
Does Expedia offer Book Now, Pay Later Portole vacation packages?
Your Portole getaway is meant to be a relaxing escape from your daily routine, not a reason for money-related stress. So to allow you a little more flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
Explore a world of travel with Expedia
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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.
