Portole Vacation Packages
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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!
Top Portole Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel La Scaletta Al Ponte Vecchio
Historic Centre of Florence
CA $1,389
per person
Nov 30 - Dec 5
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Florence (FLR)
9/10 Wonderful! (1,005 reviews)
The hotel is in a centrally located area with very close proximity (walking) to major museums and shopping with no need for a car.
Room was fairly clean but it seems long overdue for an update.
Breakfast fee is €10 per day which is very reasonable with many choices of hot and cold items.
The staff are very helpful and friendly and that is a great asset to the hotel.
Reviewed on Sep 22, 2026
The Moon Boutique Hotel & Spa
Historic Centre of Florence
CA $1,391
per person
Nov 30 - Dec 5
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Florence (FLR)
9.6/10 Exceptional! (592 reviews)
Great location. We suggest taking the river down to the city center every day. The free breakfast and coffee is great way to start your day. Schedule a spa day at least once so you can relax before the walk to dinner! Reception was super nice and even helped us call a taxi.
Reviewed on Sep 21, 2026
Grand Hotel Cavour
Historic Centre of Florence
CA $1,422
per person
Nov 30 - Dec 5
found 13 hours ago
Roundtrip flight included
Toronto (YTO) 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
Bernini Palace
Historic Centre of Florence
CA $1,810
per person
Nov 30 - Dec 5
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Florence (FLR)
9.8/10 Exceptional! (1,008 reviews)
Beautiful, historic property in the very heart of Florence. The staff makes you feel special. The room was very nice, silent and had a very comfortable bed.
Reviewed on Sep 22, 2026
Donati Luxury Tower Suites
Historic Centre of Florence
CA $2,189
per person
Nov 30 - Dec 5
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Florence (FLR)
9.8/10 Exceptional! (73 reviews)
We loved this property. The room and view are beautiful. There are excellent restaurants and shopping around the corner.
Reviewed on Sep 21, 2026
Ready to book your vacation to Portole?
Portole Hotel Deals
Villa di Piazzano - Small Luxury Hotel of the World
Localita Piazzano, C.P. 6 Cortona AR
CA $908
CA $1,012 total
Oct 1 - Oct 2
includes taxes & fees
9.8/10 Exceptional! (251 reviews)
"Stunning little hotel with the most beautiful setting, gardens and pool. The room was exceptionally appointed clean. The best part of the stay was the restaurant. The best meals we had on our entire trip. Definitely recommend hiring e-bikes and riding up to Cortona!"
Reviewed on Sep 20, 2026
Precise Tale Poggio Alla Sala
Via Di Poggio Alla Sala, 10 Montepulciano SI
Fully refundableReserve now, pay when you stay
CA $703
CA $783 total
Sep 27 - Sep 28
includes taxes & fees
9.6/10 Exceptional! (172 reviews)
"We enjoyed this picturesque hotel for a night of R&R. We especially liked arranging for e bikes to be delivered and taking the back gravel roads to look around. The second day we ran the same route."
Reviewed on Sep 22, 2026
Nuovo Etruria Resort
Via di S. Martino snc Montepulciano SI
Fully refundable
CA $163
CA $185 total
Oct 22 - Oct 23
includes taxes & fees
9.2/10 Wonderful! (130 reviews)
"The staff was very attentive and helpful specially Alfredo. He is terrific! My only complaint was a persistent low level hum that was noticeable at night, I figured that our room was above the kitchen area and that it was the industrial size refrigerator below. The view of the town up the hill from ..."
Reviewed on Sep 22, 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
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
CA $136
per adult
98% of travellers recommend
Montepulciano: Artisan Heroic Wine Tasting at the Terrace
CA $81
per adult
Oil museum and oil mill in Tuscany: tour and tasting
CA $32
per adult
Frequently asked questions
How much does a Portole vacation package cost?
Offering excellent value package deals from CA $1,389 on Expedia, you'll be thrilled with how little a vacation to Portole costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Portole?
You can usually find reduced prices and better availability in January, February and March. Take a look at our cheap Portole vacation packages and you could get some great off-season discounts.
How many days is enough for Portole?
We'd suggest booking a Portole vacation for at least 4 days. This will allow you plenty of time to visit popular sights such as Eremo Le Celle and Belvedere, as well as explore neighbourhoods like Cortona Old Town and Sodo. You might even be able to squeeze in one or two day trips outside of Portole.
How to find the best Portole package deals?
Use Expedia's handy filters to find some of the best Portole package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or look for Portole package deals in the low season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Portole vacation as a package?
You can enjoy significant savings on your Portole getaway by booking a customized vacation package. Check the "Package" heading, then select your travel dates and destination to view some great airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Portole?
Secure incredible discounts by reserving your flights in advance with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for a spur-of-the-moment Portole escape.
How to plan a trip to Portole?
- Pick your travel dates: What you want to do in Portole and your preferred season can help you decide when to travel.
- Set your budget: Consider expenses like food, flights and transportation when working out how much to put aside for your trip to Portole. Then, pick a hotel that suits your budget, whether that's an affordable option or a swankier getaway.
- Set the duration of your trip: Start by compiling a list of the activities and attractions you want to get to in Portole. Then, estimate how long you'll need for each, along with any travel time.
- Combine your accommodations and airfare: After you've settled on your dates and duration, lock in the right Portole vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
