Portole Vacations from $1,106
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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
$1,115
per person
Sep 29 - Oct 3
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
7.4/10 Good! (1,011 reviews)
Chambre plus étroite, mais propre. Staff sympa. Notre douche coulait dans la salle de bain et le jet traversait le haut de la porte. Nous n’avons pas aimé le petit buffet déjeuner, manque de fraîcheur (pain/croissant). Cependant, une belle vue pour le petit déjeuner.
Reviewed on Aug 7, 2026
Aurum Uffizi
Historic Centre of Florence
$1,188
per person
Sep 10 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
7.6/10 Good! (1,004 reviews)
The room was clean and air conditioning worked well for the size of room. However, the room was a little small for a family of four.
The location was one of the best aspects of the hotel: it was right in the historic centre and near all the attractions.
Staff were also very helpful, promptly responding to our requests.
Reviewed on Aug 2, 2026
Relais Uffizi, Tailor made Hotel
Historic Centre of Florence
$1,326
per person
Oct 19 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
9.2/10 Wonderful! (154 reviews)
While the bathrooms were clean I was very disappointed to see a stain on my bedsheets.
Reviewed on Aug 2, 2026
What to do in Portole
Tasting Tour in One of The Most Beautiful Cellars in the World
$38
per adult
100% of travellers recommend
Montepulciano Wine Tasting in the Tuscan Countryside
$28
per adult
Portole Hotel Deals
Precise Tale Poggio Alla Sala
Via Poggio alla Sala 10 Montepulciano SI
Fully refundableReserve now, pay when you stay
$490 nightly
$546 total
Aug 20 - Aug 21
Total with taxes and fees
9.6/10 Exceptional! (157 reviews)
"The place it’s an Amazing. Very clean. Is more beautiful than the pictures."
Reviewed on Aug 2, 2026
Villa di Piazzano - Small Luxury Hotel of the World
Localita Piazzano, C.P. 6 Cortona AR
$630 nightly
$702 total
Aug 18 - Aug 19
Total with taxes and fees
9.8/10 Exceptional! (241 reviews)
"Very clean and very quiet"
Reviewed on Jul 15, 2026
Monastero di Cortona Hotel & Spa
Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
$290 nightly
$328 total
Aug 23 - Aug 24
Total with taxes and fees
10/10 Exceptional! (303 reviews)
"Everything was absolutely perfect and we would happily go back."
Reviewed on Aug 6, 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 $1,106 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.
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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.
