Portole Vacations from $582

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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.
Residenza Hotel Cimabue

Residenza Hotel Cimabue

3 out of 5
Historic Centre of Florence
Price was $772, price is now $582 per person
$582
per person
Nov 20 - Nov 25
found 19 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
7.6/10 Good! (365 reviews)
Nice enough if your on a budget. Quiet area 10 mins from the cathedral... Bit run down but we needed something cheao and cheerful

Reviewed on Jun 28, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $1,388, price is now $953 per person
$953
per person
Nov 2 - Nov 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,008 reviews)
Great location for checking out the Uffizi, Galileo Museum, and

Reviewed on Sep 29, 2025

Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Price was $911, price is now $661 per person
$661
per person
Nov 21 - Nov 25
found 1 hour ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
8.6/10 Excellent! (472 reviews)
Great little hotel. Everything is within walking distance. The view from the terrace was amazing.

Reviewed on Aug 6, 2025

Relais Uffizi, Tailor made Hotel

Relais Uffizi, Tailor made Hotel

4 out of 5
Historic Centre of Florence
Price was $1,148, price is now $843 per person
$843
per person
Nov 14 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.4/10 Exceptional! (112 reviews)
The staff is so helpful especially the front desk . He’s friendly , polite , have a nice smile despite asking several favor . The breakfast is very good . They have delicious home made pastries and bread . They cook the eggs , any preference as part of the free breakfast . They have freshly squeezed orange juice , which is not common now a days in European hotels. They used to , but a lot of the hotels omit that now . They give you now box orange , which is not good for you

Reviewed on Sep 24, 2025

Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

4 out of 5
Historic Centre of Florence
Price was $1,064, price is now $787 per person
$787
per person
Nov 14 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
8.8/10 Excellent! (915 reviews)
Very nice hotel,cosy and quiet, in an historical building and close to all the attractionsJust one minute from Ponte Vecchio . There are plenty of options for parking and a great choice of restaurants. Plus the roof top restaurant is excellent

Reviewed on Sep 29, 2025

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Discover the most popular places to visit in Portole

Cortona featuring heritage architecture

Piazza della Repubblica

Find out about the history of Cortona with a stop at Piazza della Repubblica. Make time to visit the cathedral and monuments while you're in the area.

Piazza della Repubblica

Villa Bramasole

You can learn about the history of Cortona with a trip to Villa Bramasole. You can enjoy the wineries while in the area.

Villa Bramasole

Cortona Cathedral

Cortona Cathedral is just one of the places to see in Cortona, so why not enjoy the other things to explore during your travels? Experience the area's museums and musical theater.

Cortona Cathedral

What to do in Portole

Montepulciano Wine Tasting in the Tuscan Countryside

Montepulciano Wine Tasting in the Tuscan Countryside

$30
per adult
Montepulciano Wine Tasting in the Tuscan Countryside
3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch

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

$105
per adult
100% 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

$24
per adult
Oil museum and oil mill in Tuscany: tour and tasting
See all activities in Portole

Portole Hotel Deals

A Point Arezzo Park Hotel

A Point Arezzo Park Hotel

4 out of 5
Loc. Battifolle, 36/T, A1 exit Arezzo, Arezzo, AR
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $124 total per night from Oct 20 to Oct 21
$124 total
Oct 20 - Oct 21
Total with taxes and fees
7.6/10 Good! (144 reviews)
Meh
"This hotel has so much potential, but many details are missing. From music to create a pleasant atmosphere in the communal areas, especially restaurant and breakfast space. (So awkward to hear everyone chew their food around you and the kitchen staff comments in the background) To electrical jobs ..."

Reviewed on Jul 3, 2025

A Point Arezzo Park Hotel
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
Fully refundableReserve now, pay when you stay
$450 nightly
The price is $504 total per night from Oct 30 to Oct 31
$504 total
Oct 30 - Oct 31
Total with taxes and fees
9.6/10 Exceptional! (223 reviews)
"I stayed at Villa di Piazzano for two nights and overall had a lovely experience. The check-in process was seamless, and the staff were warm, professional, and very attentive, which set a great tone from the start. The property itself is absolutely gorgeous, with beautiful grounds and a peaceful ..."

Reviewed on Sep 23, 2025

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
$322 nightly
The price is $364 total per night from Oct 28 to Oct 29
$364 total
Oct 28 - Oct 29
Total with taxes and fees
9.8/10 Exceptional! (239 reviews)
"Beautiful, unique property! Stunning views of the countryside. The staff were all very helpful and friendly. We will definitely recommend!"

Reviewed on Sep 27, 2025

Monastero di Cortona Hotel & Spa
See all 4,816 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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Frequently asked questions

How much does a Portole vacation package cost?
You can snap up a vacation package to this top destination from $582 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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Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.