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 Villa Liana

Hotel Villa Liana

3 out of 5
Historic Centre of Florence
Price was CA $1,506, price is now CA $1,129 per person
CA $1,129
per person
Dec 1 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
8.8/10 Excellent! (373 reviews)
My first day/night was not good. I was in a room that faced the traffic. Even with the shutters closed, it did nothing to alleviate the noise. The traffic didn't stop until midnight. The next morning I asked if I could be moved. Thankfully a room facing the quiet courtyard was found. Breakfast was very good, with many choices in a charming historic room.

Reviewed on Oct 14, 2026

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was CA $1,948, price is now CA $1,254 per person
CA $1,254
per person
Dec 1 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
7.6/10 Good! (1,003 reviews)
.

Reviewed on Oct 27, 2026

Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Price was CA $2,501, price is now CA $1,672 per person
CA $1,672
per person
Jan 9 - Jan 16
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Florence (FLR)
8.6/10 Excellent! (508 reviews)

Hotel Duomo Firenze

Hotel Duomo Firenze

3 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was CA $3,243, price is now CA $2,360 per person
CA $2,360
per person
Dec 1 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
9.2/10 Wonderful! (1,003 reviews)
Everything was perfect,we loved everything,staff very nice

Reviewed on Oct 27, 2026

Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

4 out of 5
Historic Centre of Florence
Price was CA $2,108, price is now CA $1,536 per person
CA $1,536
per person
Dec 1 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
9/10 Wonderful! (1,000 reviews)
We had a wonderful stay here. Only two nights, but the hotel was exactly what we needed!

Reviewed on Oct 25, 2026

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Portole Hotel Deals

Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

5 out of 5
Localita Piazzano, C.P. 6 Cortona AR
The price is CA $951 per night from Oct 29 to Oct 30
CA $951
CA $1,058 total
Oct 29 - Oct 30
includes taxes & fees
Villa di Piazzano - Small Luxury Hotel of the World
Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Via Di Poggio Alla Sala, 10 Montepulciano SI
Get rates
Precise Tale Poggio Alla Sala
Nuovo Etruria Resort

Nuovo Etruria Resort

4 out of 5
Via di S. Martino snc Montepulciano SI
Fully refundable
The price is CA $141 per night from Nov 1 to Nov 2
CA $141
CA $163 total
Nov 1 - Nov 2
includes taxes & fees
9.2/10 Wonderful! (151 reviews)
"Beautiful and perfect stay in Montepulciano!"

Reviewed on Oct 27, 2026

Nuovo Etruria Resort
See all 4,343 properties in Portole
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.
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What to do in Portole

3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch

From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch

CA $189
per adult
98% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
Montepulciano Wine Tasting in the Tuscan Countryside

Montepulciano Wine Tasting in the Tuscan Countryside

CA $40
per adult
Montepulciano Wine Tasting in the Tuscan Countryside
Vino Nobile di Montepulciano winery tour and tasting

Vino Nobile di Montepulciano winery tour and tasting

CA $48
per adult
Vino Nobile di Montepulciano winery tour and tasting
See all activities in Portole

Frequently asked questions

How much does a Portole vacation package cost?
Offering excellent value package deals from CA $1,129 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?

  1. Pick your travel dates: What you want to do in Portole and your preferred season can help you decide when to travel.
  2. 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.
  3. 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.
  4. 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.