Pienza Holidays

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Pienza Holiday

Our pick of the best 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 NZ$267 per night from 22 Nov to 23 Nov
NZ$267
22 Nov - 23 Nov
includes taxes & fees
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 NZ$280 per night from 16 Nov to 17 Nov
NZ$280
16 Nov - 17 Nov
includes taxes & fees
9.4/10 Exceptional! (171 reviews)
"It was a very nice Hotel and the staff were very helpful."

Reviewed on 6 Nov 2026

Hotel San Gregorio
Agriturismo Il Macchione

Agriturismo Il Macchione

S.P. 71 Per S. Anna in Camprena Pienza SI
The price is NZ$240 per night from 12 Nov to 13 Nov
NZ$240
12 Nov - 13 Nov
includes taxes & fees
9.6/10 Exceptional! (85 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 6 Oct 2026

Agriturismo Il Macchione
See all 5,830 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

Tasting Tour in One of The Most Beautiful Cellars in the World

Tasting Tour in One of The Most Beautiful Cellars in the World

NZ$65
per adult
100% of travellers recommend
Tasting Tour in One of The Most Beautiful Cellars in the World
Montepulciano: Winery Tour and Tasting

Montepulciano: Winery Tour and Tasting

NZ$69
per adult
100% of travellers recommend
Montepulciano: Winery Tour and Tasting
Montepulciano Wine Tasting in the Tuscan Countryside

Montepulciano Wine Tasting in the Tuscan Countryside

NZ$49
per adult
Montepulciano Wine Tasting in the Tuscan Countryside
See all activities in Pienza

Frequently asked questions

How much does a Pienza holiday package cost?
You can snap up a holiday package to this popular destination on Expedia. However, how much your holiday 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 holiday packages and you could score some great off-season discounts.
How many days is enough for Pienza?
The ideal length for your Pienza holiday 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 holiday 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 holiday.
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 holiday package as soon as possible.
Is it cheaper to book a Pienza holiday as a package?
You can enjoy significant savings on your Pienza retreat by booking a personalised holiday package. Click on the "Package" heading, then enter your destination and travel dates to see the best airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a holiday 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 accommodation: After you've settled on your trip dates and duration, lock in the right Pienza holiday package for you.

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