Piana Vacations from $1,467

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Your Piana Vacation

From its highlights to its hidden gems, this city is best experienced with a Piana vacation package. Find somewhere to stay in Contrada Castello, which is great for dining, views and culture. When the time comes to go out and explore, be sure to put Palazzo della Corgna and Rocca del Leone on the itinerary for your trip to Piana. Don't delay your visit to this destination any longer. Your ultimate Piana vacation is a few quick clicks away with Expedia.

The Latest Piana vacation packages

Price found within the past 48 hours. Click for updated prices.
Residenza Porta Guelfa

Residenza Porta Guelfa

3 out of 5
Price was $1,498, price is now $1,467 per person
$1,467
per person
Nov 4 - Nov 6
found 17 hours ago
Roundtrip flight included
Kansas City (MCI) to Ancona (AOI)
8.2/10 Very Good! (46 reviews)
Excellent location, wonderful staff. The beds could use some upgrades, but the building and pool were lovely.

Reviewed on Jul 17, 2018

Ascesi Resort

Ascesi Resort

5 out of 5
Price was $1,859, price is now $1,771 per person
$1,771
per person
Nov 4 - Nov 6
found 17 hours ago
Roundtrip flight included
Kansas City (MCI) to Ancona (AOI)
10/10 Exceptional! (1 review)
Borgo Mandoleto

Borgo Mandoleto

3 out of 5
Price was $1,499, price is now $1,468 per person
$1,468
per person
Nov 4 - Nov 6
found 17 hours ago
Roundtrip flight included
Kansas City (MCI) to Ancona (AOI)
8.8/10 Excellent! (24 reviews)
Pleasant atmosphere, friendly staff. Noce pool

Reviewed on Jul 1, 2023

TH Assisi - Hotel Cenacolo

TH Assisi - Hotel Cenacolo

4 out of 5
Price was $1,513, price is now $1,486 per person
$1,486
per person
Nov 4 - Nov 6
found 17 hours ago
Roundtrip flight included
Kansas City (MCI) to Ancona (AOI)
9.2/10 Wonderful! (588 reviews)
A refill of water in the room would have been appreciate. Apart from that v frendly helpful staff and good breakfast.

Reviewed on Aug 23, 2025

Ristoro Appennino

Ristoro Appennino

3 out of 5
Price was $1,504, price is now $1,480 per person
$1,480
per person
Nov 4 - Nov 6
found 17 hours ago
Roundtrip flight included
Kansas City (MCI) to Ancona (AOI)
9.6/10 Exceptional! (8 reviews)
Wonderfully friendly service and amazing place. If you want something away from …. Well everything else.

Reviewed on Sep 6, 2023

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Discover the most popular places to visit in Piana

Rocca del Leone

Rocca del Leone

You can learn about the history of Castiglione del Lago when you stop by Rocca del Leone. Stroll along the area's lakeside or simply enjoy its wineries.

Rocca del Leone

Palazzo della Corgna

5/5(1 review)

You can study the exhibits at Palazzo della Corgna, a museum with a storied past, during your trip to Castiglione del Lago. Stroll along the area's lakeside or simply enjoy its wineries.

Palazzo della Corgna

What to do in Piana

3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch

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

$104
per adult
100% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
Montepulciano: Wine Tour and tasting

Montepulciano: Wine Tour and tasting

$61
per adult
100% of travellers recommend
Montepulciano: Wine Tour and tasting
Montepulciano: Tuscan Winery Tour with Wine Tasting & Meal

Montepulciano: Tuscan Winery Tour with Wine Tasting & Meal

$116
per adult
100% of travellers recommend
Montepulciano: Tuscan Winery Tour with Wine Tasting & Meal
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Piana Hotel Deals

Hotel Relais II Chiostro di Pienza

Hotel Relais II Chiostro di Pienza

4 out of 5
Corso Rossellino 26, Pienza, SI
$120 nightly
The price is $140 total per night from Sep 14 to Sep 15
$140 total
Sep 14 - Sep 15
Total with taxes and fees
Hotel Relais II Chiostro di Pienza
Hotel Panoramic

Hotel Panoramic

3 out of 5
Via di Villa Bianca, 8, Montepulciano, SI
$68 nightly
The price is $79 total per night from Oct 1 to Oct 2
$79 total
Oct 1 - Oct 2
Total with taxes and fees
Hotel Panoramic
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
$401 nightly
The price is $450 total per night from Sep 29 to Sep 30
$450 total
Sep 29 - Sep 30
Total with taxes and fees
Monastero di Cortona Hotel & Spa
See all 5,174 properties in Piana
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 Piana vacation package cost?
Offering excellent value package deals from $1,467 on Expedia, you'll be pleasantly surprised at how much a vacation to Piana costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Piana?
You can usually find reduced prices and greater availability in October, November and December. Check out our cheap Piana vacation packages and you could land some great off-season deals.
How many days is enough for Piana?
Usually, a handful of days is enough to explore the top sights during your Piana vacation. But if you want to have time to kick back or go on day tours, consider extending your trip.
How to find the best Piana package deals?
Start your search for a Piana package deal by entering your preferred travel dates and destination under our "Packages" tab. Then add some filters, like "Property type" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Piana package deal straight away, simply change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Piana adventure off to a flying start.
Is it cheaper to book a Piana vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking hotels and flights individually. Better still, you can customize your Piana getaway to fit your exact needs. Pick 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 Piana?
If you're planning a spur-of-the-moment Piana trip, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land incredible deals on your flights and hotels by booking well in advance.
Does Expedia offer Book Now, Pay Later Piana vacation packages?
If you're like us, you love going away but don't love 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 break down the cost of your Piana trip 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 see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.