Poggiolo Vacations from $644

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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
Save 100% on your flight
Price was $1,096, price is now $644 per person
$644
per person
Nov 13 - Nov 18
found 22 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,004 reviews)
Very clean, aircon definitely welcome in summer temperatures, breakfast buffet very good. All within walkable distance of the Palazzo Vecchio and other attractions.

Reviewed on Aug 30, 2025

L'Andana

L'Andana

5 out of 5
Save 100% on your flight
Price was $2,626, price is now $1,752 per person
$1,752
per person
Oct 24 - Oct 31
found 15 hours ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
9.4/10 Exceptional! (80 reviews)
What an amazing place I hope to get back here next year again everybody was super nice. Property was super nice. It is quite relaxing. Great food apparently a great wine as well but I don’t drink. I highly recommend anybody to go.

Reviewed on Jul 5, 2025

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Cortona Old Town
Save 100% on your flight
Price was $2,080, price is now $1,456 per person
$1,456
per person
Oct 24 - Oct 31
found 15 hours ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
10/10 Exceptional! (230 reviews)
Beautiful property, magical, great friendly staff, fantastic breakfast. Everything was perfect

Reviewed on Aug 7, 2025

The Club House

The Club House

5 out of 5
Save 100% on your flight
Price was $2,450, price is now $1,717 per person
$1,717
per person
Oct 24 - Oct 31
found 15 hours ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
10/10 Exceptional! (2 reviews)
Excellent overall. Amenities. Service. Food. Vibe. All top notch

Reviewed on Sep 2, 2025

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,514, price is now $934 per person
$934
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,008 reviews)
Close to centre of Florence, room ok, clean

Reviewed on Aug 28, 2025

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Discover the most popular places to visit in Poggiolo

Tennis Club Castiglionese

You can take time to visit Tennis Club Castiglionese during your travels 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 Tour and tasting

Montepulciano: Wine Tour and tasting

$61
per adult
100% of travellers recommend
Montepulciano: Wine Tour and tasting
Montepulciano Wine Tasting in the Tuscan Countryside

Montepulciano Wine Tasting in the Tuscan Countryside

$29
per adult
Montepulciano Wine Tasting in the Tuscan Countryside
WELCOME!

Private visit to the House of Grand Duke Leopold of Tuscany with invitation

$47
per adult
Private visit to the House of Grand Duke Leopold of Tuscany with invitation
See all activities in Poggiolo

Poggiolo 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
$426 nightly
The price is $475 total per night from Sep 8 to Sep 9
$475 total
Sep 8 - Sep 9
Total with taxes and fees
Precise Tale Poggio Alla Sala
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
$339 nightly
The price is $382 total per night from Sep 3 to Sep 4
$382 total
Sep 3 - Sep 4
Total with taxes and fees
Monastero di Cortona Hotel & Spa
B&B Hotel Arezzo

B&B Hotel Arezzo

3 out of 5
Via Einstein, 4, Arezzo, AR
Fully refundableReserve now, pay when you stay
$70 nightly
The price is $85 total per night from Sep 8 to Sep 9
$85 total
Sep 8 - Sep 9
Total with taxes and fees
B&B Hotel Arezzo
See all 5,023 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.

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Frequently asked questions

How much does a Poggiolo vacation package cost?
Offering excellent value package deals from $644 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.