Pienza Vacations from ￥289,042
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The Latest Pienza Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Aurum Firenze
Historic Centre of Florence
￥289,042
per person
Dec 25 - Dec 29
found 10 hours ago
Roundtrip flight included
Tokyo (TYO) to Florence (FLR)
7.4/10 Good! (1,015 reviews)
We encountered ants twice. We were given a bottle of raid and kept food in fridge or hanging up high.
Appreciated the 24 hour service. There was a medical emergency and the front desk took great care of us. And they had no problem with us staying for an extra 2 days.
Reviewed on Oct 12, 2026
Hotel La Scaletta Al Ponte Vecchio
Historic Centre of Florence
￥326,704
per person
Dec 25 - Dec 29
found 10 hours ago
Roundtrip flight included
Tokyo (TYO) to Florence (FLR)
9/10 Wonderful! (1,002 reviews)
Great location! Staff was friendly and helpful. Had a wonderful stay Highly recommend!
Reviewed on Oct 11, 2026
Hotel degli Orafi
Historic Centre of Florence
￥336,176
per person
Dec 25 - Dec 29
found 10 hours ago
Roundtrip flight included
Tokyo (TYO) to Florence (FLR)
9.6/10 Exceptional! (1,005 reviews)
The perfect hotel for your Florence getaway. Charming hotel with a friendly and helpful staff. The location could not be more perfect. Full breakfast is served in the most elegant room. The rooftop bar is the best way to start or end your evening.
Reviewed on Oct 8, 2026
Find the Best Pienza Vacation Packages
Pienza Hotel Deals
Hotel San Gregorio
Via Della Madonnina 4 Pienza SI
￥20,290
￥23,383 total
Nov 8 - Nov 9
includes taxes & fees
9.4/10 Exceptional! (162 reviews)
"Great location. Clean and quiet with good breakfast"
Reviewed on Oct 12, 2026
Hotel Corsignano
Via Della Madonnina 11 Pienza SI
￥18,423
￥21,329 total
Nov 11 - Nov 12
includes taxes & fees
Agriturismo Il Macchione
S.P. 71 Per S. Anna in Camprena Pienza SI
￥22,495
￥25,453 total
Nov 5 - Nov 6
includes taxes & fees
9.6/10 Exceptional! (81 reviews)
"We stayed at the olive Farmhouse across the street from the main property. Rooms were cozy and clean with some interesting toiletries to use (made from olive oil). The property also has a range of activities (extra) to choose from. Just a note that eventhough the farmhouse is close to the main property, ..."
Reviewed on Oct 6, 2026
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.
Stay near popular Pienza attractions
Pienza Cathedral
9.4/10 (460 reviews)
Pope Pius II's Renaissance masterpiece showcases harmonious Gothic elements and luminous three-nave design. Arrive early to admire the 15th-century Sienese paintings and enjoy panoramic Tuscan views from the corridor.
Historic Centre of Pienza
9.6/10 (42 reviews)
Pienza's Historic Centre showcases Pope Pius II's Renaissance ideal city vision with harmonious architecture. Explore cobblestone streets, the Cathedral and Palazzo Piccolomini, and sample the town's famous pecorino cheese.
Palazzo Piccolomini
9.4/10 (199 reviews)
This Renaissance masterpiece was Pope Pius II's summer residence, designed by Bernardo Rossellino. From its hanging gardens, savor breathtaking panoramic views across the Val d'Orcia's rolling Tuscan landscape.
Piazza Pio II
9.2/10 (44 reviews)
This Renaissance masterpiece, designed by Bernardo Rossellino in 1459, showcases perfect architectural harmony at Pienza's heart. Explore the cathedral's artworks and enjoy sweeping Tuscan views from the elegant terrace.
Monastery of Sant'Anna in Camprena
This former monastery in the Tuscan hills showcases remarkable Renaissance frescoes in a tranquil setting. Savor authentic regional cuisine while staying overnight in the historic stone buildings.
Palazzo Vescovile
9.0/10 (12 reviews)
The Palazzo Vescovile showcases a captivating collection of religious art from the 14th-15th centuries. Admire Pietro Lorenzetti's Madonna di Monticchiello while exploring eleven rooms filled with sacred treasures.
Palazzo Borgia
8.8/10 (21 reviews)
This Renaissance palace houses the Museo Diocesano with masterpieces by Lorenzetti and Signorelli. Admire 12th-century crucifixes and medieval art while exploring the former residence of Cardinal Rodrigo Borgia.
Pieve di Corsignano
9.0/10 (17 reviews)
This 10th-century Romanesque church features a circular bell tower and Pope Pius II's baptismal font. Inside, soft light illuminates ancient stone carvings across its three-naved interior.
What to do in Pienza
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
￥19,639
per adult
98% of travellers recommend
Montepulciano Wine Tasting in the Tuscan Countryside
￥4,504
per adult
Frequently asked questions
How much does a Pienza vacation package cost?
You can snap up a vacation package to this popular destination from ￥289,042 on Expedia. However, how much your vacation to Pienza costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Pienza?
You can usually find lower rates and better availability in December, January and February. Browse our cheap Pienza vacation packages and you could score some great off-season discounts.
How many days is enough for Pienza?
The ideal length for your Pienza vacation depends on what you'd like to see. Typically, a few days to a week will give you time to check out all the top attractions and explore some hidden spots along the way.
Is it worth booking a vacation package to Pienza?
Pienza has everything you need for an amazing break — walking trails, hiking and festivals are just the start. Whether you want to visit sights like Palazzo Piccolomini and Historic Centre of Pienza, or take the road less traveled, you'll have plenty to experience on your Pienza vacation.
How to find the best Pienza package deals?
Use Expedia's filter tool to find some great Pienza package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or look for Pienza package deals in the off-peak season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a Pienza vacation as a package?
You can enjoy significant savings on your Pienza retreat by booking a personalized vacation package. Click on the "Package" heading, then enter your destination and travel dates to see the best airfares and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Pienza?
If you have your Pienza travel dates locked in, book as early as you can to bag some outstanding deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to Pienza?
- Pick your travel dates: The things you plan to do in Pienza and your preferred season will help you decide when to go.
- Budget wisely: As well as the price of your stay, you should factor in other expenses too. These include transportation, food and flights. Also, put aside a little extra for unexpected expenses that may come up during your trip to Pienza.
- Decide how long to go away for: Now that you know more about Pienza, you can figure out the perfect length of your break. Pull together a draft plan and give yourself enough time to cover everything you want to do.
- Bundle your airfare and accommodations: After you've settled on your trip dates and duration, lock in the right Pienza vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
