Portole Vacations from $1,068
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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.
Hotel La Scaletta Al Ponte Vecchio
Historic Centre of Florence
$1,271
per person
Dec 6 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9/10 Wonderful! (1,002 reviews)
We had a wonderful stay here. Only two nights, but the hotel was exactly what we needed!
Reviewed on Oct 25, 2026
Villa Tolomei Hotel & Resort
Oltrarno
$1,252
per person
Dec 6 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
8.8/10 Excellent! (445 reviews)
Beautiful hotel! We didn't realize the pool would be closed when we were there, but otherwise excellent stay.
Reviewed on Oct 13, 2026
Hotel Hermitage
Historic Centre of Florence
$1,297
per person
Dec 6 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9/10 Wonderful! (1,002 reviews)
Loved this property! Great location. Charming Ralph Lauren Vibe. Most importantly, the room was cleaned daily, desk staff was beyond helpful and friendly, amenities were great. Stay here. You will love it!
Reviewed on Oct 21, 2026
Hotel Balestri
Historic Centre of Florence
$1,473
per person
Dec 6 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.4/10 Exceptional! (1,003 reviews)
Had a great room with access to a rooftop patio and a spectacular view
Reviewed on Oct 21, 2026
What to do in Portole
Montepulciano Wine Tasting in the Tuscan Countryside
$28
per adult
Montepulciano: Winery Tour and Tasting
$39
per adult
100% of travellers recommend
Montepulciano: Tuscan Cooking Class with Fresh Pasta & Wine
$90
per adult
Portole Hotel Deals
Villa di Piazzano - Small Luxury Hotel of the World
Localita Piazzano, C.P. 6 Cortona AR
$681 nightly
$758 total
Oct 27 - Oct 28
Total with taxes and fees
Precise Tale Poggio Alla Sala
Via Di Poggio Alla Sala, 10 Montepulciano SI
Nuovo Etruria Resort
Via di S. Martino snc Montepulciano SI
$105 nightly
$121 total
Oct 29 - Oct 30
Total with taxes and fees
9.2/10 Wonderful! (149 reviews)
"Location and property are very nice. Shower was very small with a seat in the middle making it difficult to use. Breakfast was good. The room itself was just ok. Our room in particular was extremely hot. A door in the front and a window in the bathroom. No cross ventilation and the A/C had been turned ..."
Reviewed on Oct 24, 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 $1,068 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.
