Portole Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Price was CA $2,343, price is now CA $1,549 per person
CA $1,549
per person
Oct 18 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
7.4/10 Good! (1,011 reviews)

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Price was CA $7,301, price is now CA $4,397 per person
CA $4,397
per person
Aug 30 - Sep 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Florence (FLR)
9.6/10 Exceptional! (151 reviews)
Magical location, pools, staff, property.

Reviewed on Jul 19, 2026

Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Price was CA $3,791, price is now CA $2,399 per person
CA $2,399
per person
Oct 2 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
8.6/10 Excellent! (493 reviews)
Very good location. Clean hotel. Our ac was broken but they handled us a new room inmediately. The hotel is confortable and size of the rooms are decent. Bigger than average in the area.

Reviewed on Jun 26, 2026

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was CA $2,395, price is now CA $1,568 per person
CA $1,568
per person
Oct 18 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
7.6/10 Good! (1,003 reviews)
The location of this hotel is fantastic and central to all the major sights. We were able to walk to every major landmark between 4-10 minutes. The staff were lovely and hard working. The AC, shower/hot water worked great. The breakfast was a typical continental style and I found it satisfactory to a hotel this size. The one thing that was challenging was getting a regular wifi signal. Overall, great stay for a family of 4.

Reviewed on Jul 24, 2026

Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

4 out of 5
Historic Centre of Florence
Price was CA $3,298, price is now CA $2,276 per person
CA $2,276
per person
Sep 1 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Florence (FLR)
9/10 Wonderful! (1,004 reviews)
i don't like the hotel has a small bathroom . everything is close to restaurants and stuff

Reviewed on Jul 26, 2026

Ready to book your vacation to Portole?

 

Choose your dates

Portole Hotel Deals

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Via Poggio alla Sala 10 Montepulciano SI
Fully refundableReserve now, pay when you stay
The price is CA $830 per night from Aug 12 to Aug 13
CA $830
CA $923 total
Aug 12 - Aug 13
includes taxes & fees
9.6/10 Exceptional! (155 reviews)
"Magical location, pools, staff, property."

Reviewed on Jul 19, 2026

Precise Tale Poggio Alla Sala
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 $976 per night from Aug 20 to Aug 21
CA $976
CA $1,087 total
Aug 20 - Aug 21
includes taxes & fees
9.8/10 Exceptional! (241 reviews)
"Very clean and very quiet"

Reviewed on Jul 15, 2026

Villa di Piazzano - Small Luxury Hotel of the World
Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
The price is CA $449 per night from Aug 16 to Aug 17
CA $449
CA $506 total
Aug 16 - Aug 17
includes taxes & fees
10/10 Exceptional! (299 reviews)
"Beautiful oasis in a beautiful town"

Reviewed on Jul 25, 2026

Monastero di Cortona Hotel & Spa
See all 4,435 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

What to do in Portole

Wine & Music on the Terrace

Wine & Music on the Terrace

CA $32
per adult
Wine & Music on the Terrace
3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch

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

CA $153
per adult
98% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
Oil museum and oil mill in Tuscany: tour and tasting

Oil museum and oil mill in Tuscany: tour and tasting

CA $32
per adult
Oil museum and oil mill in Tuscany: 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 $1,549 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.