Pienza Vacations from ￥345,928

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The Latest Pienza Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Paris

Hotel Paris

3 out of 5
Historic Centre of Florence
Price was ￥390,292, price is now ￥345,928 per person
￥345,928
per person
Sep 11 - Sep 15
found 15 hours ago
Roundtrip flight included
Nagoya (NGO) to Florence (FLR)
9/10 Wonderful! (1,008 reviews)
Very good experience, great location.

Reviewed on Jul 11, 2026

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Price was ￥485,808, price is now ￥368,643 per person
￥368,643
per person
Sep 11 - Sep 15
found 15 hours ago
Roundtrip flight included
Nagoya (NGO) to Florence (FLR)
9.6/10 Exceptional! (570 reviews)
Wonderful stay, attentive staff, very clean room. The spa facilities are very high quality and had a lovely massage. Good choices for breakfast. I would certainly recommend staying here, the spa was a particular highlight that is free for guests to use.

Reviewed on Jul 2, 2026

Hotel Garibaldi Blu

Hotel Garibaldi Blu

4 out of 5
Historic Centre of Florence
Price was ￥480,364, price is now ￥386,919 per person
￥386,919
per person
Sep 11 - Sep 15
found 15 hours ago
Roundtrip flight included
Nagoya (NGO) to Florence (FLR)
9.2/10 Wonderful! (884 reviews)
The air conditioning didn’t seem to be working consistently, our room was a bit hot. The breakfast was perfect and a great way to start our day. The location was excellent for ask the areas of Florence we wanted try see. We would highly recommend this place.

Reviewed on Jul 5, 2026

Helvetia & Bristol Firenze – Starhotels Collezione

Helvetia & Bristol Firenze – Starhotels Collezione

5 out of 5
Historic Centre of Florence
Price was ￥730,174, price is now ￥635,292 per person
￥635,292
per person
Sep 11 - Sep 15
found 15 hours ago
Roundtrip flight included
Nagoya (NGO) to Florence (FLR)
9.2/10 Wonderful! (565 reviews)
Completely charming and so centrally located to everything that it was easy to pop in and out of the hotel throughout the day. I had a room on the first floor facing the street and was initially concerned that it might be noisy but it was perfectly quiet and the room was completely dark with the shutters. I also used the gym, which was completely sufficient. Lovely experience and I would definitely go back.

Reviewed on Jul 11, 2026

25hours Hotel Florence Piazza San Paolino

25hours Hotel Florence Piazza San Paolino

4 out of 5
Historic Centre of Florence
Price was ￥421,948, price is now ￥371,770 per person
￥371,770
per person
Sep 11 - Sep 15
found 15 hours ago
Roundtrip flight included
Nagoya (NGO) to Florence (FLR)
9.4/10 Exceptional! (1,003 reviews)
Great

Reviewed on Jul 8, 2026

Find the Best Pienza Vacation Packages

Pienza Hotel Deals

Hotel Corsignano

Hotel Corsignano

4 out of 5
Via Della Madonnina 11 Pienza SI
Fully refundableReserve now, pay when you stay
The price is ￥26,073 per night from Aug 5 to Aug 6
￥26,073
￥29,787 total
Aug 5 - Aug 6
includes taxes & fees
9.4/10 Exceptional! (366 reviews)
"."

Reviewed on Jun 17, 2026

Hotel Corsignano
Hotel San Gregorio

Hotel San Gregorio

3 out of 5
Via Della Madonnina 4 Pienza SI
Fully refundableReserve now, pay when you stay
The price is ￥33,868 per night from Jul 22 to Jul 23
￥33,868
￥38,362 total
Jul 22 - Jul 23
includes taxes & fees
Hotel San Gregorio
Agriturismo Il Macchione

Agriturismo Il Macchione

S.P. 71 Per S. Anna in Camprena Pienza SI
9.6/10 Exceptional! (70 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

Get rates
Agriturismo Il Macchione
See all 6,057 properties in Pienza
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

A historic church with a bell tower, arched windows, and a central dome.

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.
See properties

What to do in Pienza

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

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

￥15,536
per adult
98% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
Seggiano: Guided Tour of the Olive Grove and Food Tasting

Seggiano: Guided Tour of the Olive Grove and Food Tasting

￥4,624
per adult
Seggiano: Guided Tour of the Olive Grove and Food Tasting
Montepulciano Gran Tour

Montepulciano Gran Tour

￥2,774
per adult
Montepulciano Gran Tour
See all activities in Pienza

Frequently asked questions

How much does a Pienza vacation package cost?
You can snap up a vacation package to this popular destination from ￥345,928 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?

  1. Pick your travel dates: The things you plan to do in Pienza and your preferred season will help you decide when to go.
  2. 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.
  3. 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.
  4. Bundle your airfare and accommodations: After you've settled on your trip dates and duration, lock in the right Pienza vacation package for you.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.