Portole Vacations from $3,521

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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.
The Gate Hotel

The Gate Hotel

4 out of 5
Price was $6,268, price is now $3,521 per person
$3,521
per person
Feb 10 - Feb 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.4/10 Good! (507 reviews)
Clean and great location for access to airport.

Reviewed on Oct 30, 2025

Allegroitalia San Gallo Firenze

Allegroitalia San Gallo Firenze

4 out of 5
San Lorenzo
Price was $6,351, price is now $3,575 per person
$3,575
per person
Feb 10 - Feb 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
8.8/10 Excellent! (1,000 reviews)
Wonderful, well-presented hotel in a great location with an excellent and generous breakfast. Immaculate, spacious rooms, great proximity to city centre and tram stop just outside.

Reviewed on Dec 16, 2025

UNA Hotels Vittoria Firenze

UNA Hotels Vittoria Firenze

4 out of 5
Oltrarno
Price was $6,357, price is now $3,580 per person
$3,580
per person
Feb 10 - Feb 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
8.4/10 Very Good! (1,000 reviews)
Perfect stay! Not only was the check-in smooth, but everything else was also satisfying. The breakfast was delicious, the staff were friendly, and the location was ideal. There wasn't a single thing I didn't like. I’ll definitely be back!

Reviewed on Jan 1, 2026

Hotel Atlantic Palace

Hotel Atlantic Palace

4 out of 5
Historic Centre of Florence
Price was $6,320, price is now $3,580 per person
$3,580
per person
Feb 10 - Feb 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (896 reviews)
I’ve stayed here a few times and I appreciate that this hotel has a great location, clean rooms and friendly and very helpful staff.

Reviewed on Nov 6, 2025

Starhotels Tuscany

Starhotels Tuscany

4 out of 5
Price was $6,311, price is now $3,575 per person
$3,575
per person
Feb 10 - Feb 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9/10 Wonderful! (1,000 reviews)
Staying here was amazing, the customer service and the design of the room. Will stay again!

Reviewed on Dec 1, 2025

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Discover the most popular places to visit in Portole

Cortona featuring heritage architecture

Piazza della Repubblica

5/5(4 reviews)

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

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
Montepulciano Wine Tasting in the Tuscan Countryside

Montepulciano Wine Tasting in the Tuscan Countryside

$29
per adult
Montepulciano Wine Tasting in the Tuscan Countryside
Montepulciano: Artisan Heroic Wine Tasting at the Terrace

Montepulciano: Artisan Heroic Wine Tasting at the Terrace

$59
per adult
Montepulciano: Artisan Heroic Wine Tasting at the Terrace
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 Arezzo AR
Fully refundableReserve now, pay when you stay
$63 nightly
The price is $76 total per night from Jan 12 to Jan 13
$76 total
Jan 12 - Jan 13
Total with taxes and fees
7.6/10 Good! (157 reviews)
The room was in quite poor condition. There was only lukewarm water, the heating was noisy, the tv didn’t work, the lights over the bed flashed and the toilet seat was loose. It was a very stylish hotel but it just needs some maintenance. The breakfast was very good and the bed was comfortable

Reviewed on Nov 14, 2025

A Point Arezzo Park Hotel
Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Via del Salvatore Cortona AR
9.8/10 Exceptional! (258 reviews)
Everything was great! Lovely hotel

Reviewed on Jan 4, 2026

Get rates
Monastero di Cortona Hotel & Spa
Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze

Via Grazianella 5 Montepulciano SI
9.6/10 Exceptional! (278 reviews)
Everything was perfect. Warm welcome, comfortable and spacious rooms, great breakfast. The staff was very kind and friendly. I also recommend the wine tasting experience. Highly recommended!

Reviewed on Dec 5, 2025

Get rates
Relais Villa Grazianella - UNA Esperienze
See all 4,336 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.

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 $3,521 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.