Poggiolo Vacations from $590

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Your Poggiolo Vacation

Let our vacation packages to Poggiolo inspire your next escape. There's loads to like about this amazing city, starting with the neighborhood of Ristonchia, which is good for views and nature. Any trip to Poggiolo needs a well-planned itinerary. Fill yours with attractions like Tennis Club Castiglionese, Cassero Tower and Archaeological Museum. A few clicks is all it takes to create the perfect Poggiolo vacation on Expedia.

The Latest Poggiolo vacation packages

Price found within the past 48 hours. Click for updated prices.
Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $892, price is now $590 per person
$590
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
7.8/10 Good! (1,000 reviews)
Breakfast was good. Staff super friendly. Overall the expected quality for the paid price.

Reviewed on Nov 20, 2025

Hotel Regency

Hotel Regency

5 out of 5
Historic Centre of Florence
Price was $2,161, price is now $1,493 per person
$1,493
per person
Jan 5 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
9.4/10 Exceptional! (439 reviews)
Loved it! Great place and very convenient

Reviewed on Jul 4, 2025

Helvetia & Bristol Firenze – Starhotels Collezione

Helvetia & Bristol Firenze – Starhotels Collezione

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $2,668, price is now $1,769 per person
$1,769
per person
Jan 24 - Jan 30
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
9.2/10 Wonderful! (544 reviews)
The nightly turndown service, front desk attentiveness, clean rooms, and wonderful doormen were all just wonderful.

Reviewed on Nov 16, 2025

Hotel degli Orafi

Hotel degli Orafi

4 out of 5
Historic Centre of Florence
Price was $1,095, price is now $729 per person
$729
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.6/10 Exceptional! (1,001 reviews)
Spacious room much bigger than an average single.

Reviewed on Nov 27, 2025

Arte' Boutique Hotel

Arte' Boutique Hotel

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,467, price is now $993 per person
$993
per person
Jan 24 - Jan 30
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
9.8/10 Exceptional! (293 reviews)
We had a great time. Thank you!

Reviewed on Nov 28, 2025

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Discover the most popular places to visit in Poggiolo

Tennis Club Castiglionese

Catch an event at Tennis Club Castiglionese during your trip to Castiglion Fiorentino. You can enjoy the wineries while in the area.

Tennis Club Castiglionese

Agricola Buccelletti Winery

You can enjoy a tasting or tour at Agricola Buccelletti Winery during your travels to La Strada-Santa Cristina. Discover the area's countryside and wineries.

Agricola Buccelletti Winery

Cassero Tower

Find out about the history of Castiglion Fiorentino when you spend time at Cassero Tower. You can enjoy the wineries while in the area.

Cassero Tower

What to do in Poggiolo

Montepulciano Wine Tasting in the Tuscan Countryside

Montepulciano Wine Tasting in the Tuscan Countryside

$29
per adult
Montepulciano Wine Tasting in the Tuscan Countryside
Oil museum and oil mill in Tuscany: tour and tasting

Oil museum and oil mill in Tuscany: tour and tasting

$23
per adult
Oil museum and oil mill in Tuscany: tour and tasting
Montepulciano Wine Tasting with typical Tuscan Cold Cuts

Montepulciano Wine Tasting with typical Tuscan Cold Cuts

$52
per adult
Montepulciano Wine Tasting with typical Tuscan Cold Cuts
See all activities in Poggiolo

Poggiolo Hotel Deals

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
$296 nightly
The price is $335 total per night from Dec 14 to Dec 15
$335 total
Dec 14 - Dec 15
Total with taxes and fees
9.8/10 Exceptional! (254 reviews)
Our arrival experience was less than stellar for a warm welcome to property. Front desk associate was very cold and accusatory of the situation we encountered outside of the property. We have traveled extensively and I expected better arrival experience. It all changed for the better when we finally ...

Reviewed on Nov 23, 2025

Monastero di Cortona Hotel & Spa
Hotel Continentale

Hotel Continentale

4 out of 5
Piazza Guido Monaco, 7 Arezzo AR
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $142 total per night from Dec 3 to Dec 4
$142 total
Dec 3 - Dec 4
Total with taxes and fees
8.4/10 Very Good! (451 reviews)
We had a last-minute stay there due to the train strike, and it was a great evening after all… The hotel was right there in the main Square plus near the train station. The staff was lovely and they have the most beautiful rooftop patio and bar. you have to check out.

Reviewed on Oct 17, 2025

Hotel Continentale
Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze

Via Grazianella 5 Montepulciano SI
$113 nightly
The price is $129 total per night from Dec 3 to Dec 4
$129 total
Dec 3 - Dec 4
Total with taxes and fees
9.6/10 Exceptional! (275 reviews)
Great room and service

Reviewed on Nov 11, 2025

Relais Villa Grazianella - UNA Esperienze
See all 4,873 properties in Poggiolo
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 Poggiolo Vacation Packages

Poggiolo Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Max Temp Winter
45ºF
Max Temp Summer
80ºF
Top Sights
Agricola Buccelletti Winery, Archaeological Museum and Municipal Art Gallery

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Frequently asked questions

How much does a Poggiolo vacation package cost?
Offering excellent value package deals from $590 on Expedia, you'll be thrilled with how little a vacation to Poggiolo costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Poggiolo?
November, December and January are great times to look for cheap Poggiolo vacation packages. Opting to travel in less busy periods means you'll typically find reduced prices on accommodations and flights.
How many days is enough for Poggiolo?
The ideal length for your Poggiolo vacation depends on what you'd like to do and see. Generally, a handful of days to a week will give you enough time to check out all the leading sights and discover some hidden gems along the way.
How to find the best Poggiolo package deals?
Landing a cheap Poggiolo package deal is easy with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, apply a few filters and see what's available. You can tweak your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to view the most economical Poggiolo package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are generally lower.
Is it cheaper to book a Poggiolo vacation as a package?
You can enjoy significant savings on your Poggiolo retreat by booking a tailored vacation package. Check the "Package" heading, then select your destination and travel dates to browse some great hotel prices and airfares. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Poggiolo?
Enjoy incredible discounts by booking your flights early with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for a spur-of-the-moment Poggiolo trip.
Does Expedia offer Book Now, Pay Later Poggiolo vacation packages?
If you're anything like us, you love exploring new places but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the cost of your Poggiolo vacation over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.