Pienza Vacations from ￥471,771
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The Latest Pienza Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel La Scaletta Al Ponte Vecchio
Historic Centre of Florence
￥471,771
per person
Oct 19 - Oct 24
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Florence (FLR)
9/10 Wonderful! (1,004 reviews)
This was my favorite hotel out of all the cities I’ve visited in Italy. The staff are kind and the hotel is in walking distance to everything. I didn’t take any taxis during my stay. It’s a 15 minute walk from the train station. It’s close to many restaurants, attractions and stores to shop. They have a beautiful roof top bar over looking Florence
Reviewed on Aug 25, 2026
The Hoxton, Florence
Historic Centre of Florence
￥486,019
per person
Oct 19 - Oct 24
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Florence (FLR)
9.4/10 Exceptional! (333 reviews)
I recommend this stay, to anyone going to Florence. This hotel is very nice and the staff was amazing
Reviewed on Aug 27, 2026
Find the Best Pienza Vacation Packages
Pienza Hotel Deals
Hotel San Gregorio
Via Della Madonnina 4 Pienza SI
￥37,034
￥41,851 total
Sep 26 - Sep 27
includes taxes & fees
Hotel Corsignano
Via Della Madonnina 11 Pienza SI
￥29,549
￥33,618 total
Aug 30 - Aug 31
includes taxes & fees
9.4/10 Exceptional! (376 reviews)
"We had an exceptional nice stay. I can highly recommend the Corsignano to anyone. It’s just a couple minutes walking distance from the old town … I will definitely stay here again on my next visit to Pienza"
Reviewed on Aug 25, 2026
Agriturismo Il Macchione
S.P. 71 Per S. Anna in Camprena Pienza SI
￥30,142
￥33,899 total
Sep 28 - Sep 29
includes taxes & fees
9.6/10 Exceptional! (72 reviews)
"We had an amazing time staying at this property: the staff were super helpful, going beyond what was expected to accommodate our late arrival. The room was very clean and cozy looking, the views surrounding the property were breathtaking, we couldn’t believe our eyes. The view of the property were ..."
Reviewed on Jun 17, 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.
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.
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.
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.
Artemisia Gallery
8.8/10 (9 reviews)
You can study the exhibits at Artemisia Gallery, a museum with a story of its own, during your trip to Pienza. While you're here, you can savor the wineries.
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.
What to do in Pienza
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
￥17,299
per adult
98% of travellers recommend
Seggiano: Guided Tour of the Olive Grove and Food Tasting
￥4,601
per adult
Tasting Tour in One of The Most Beautiful Cellars in the World
￥6,073
per adult
100% of travellers recommend
Frequently asked questions
How much does a Pienza vacation package cost?
You can snap up a vacation package to this popular destination from ￥471,771 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.
