Pienza Holidays

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Top hotels in Pienza

Hotel Relais II Chiostro di Pienza
Hotel Relais II Chiostro di Pienza
4 out of 5
Corso Rossellino 26, Pienza, SI
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8.6/10 Excellent! (565 reviews)
"Beautiful hotel in a beautifully preserved town centre. Bags of atmosphere and history and generous service and breakfasts. The hotel is in the pedestrianised old town so vehicle access and parking is not catered for. The upside however is its central location and access to local amenities on foot ..."

Reviewed on 30 May 2025

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Hotel Relais II Chiostro di Pienza
Hotel Corsignano
Hotel Corsignano
4 out of 5
Via Della Madonnina 11, Pienza, SI
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (297 reviews)
"Second time visiting Great breakfast with Richard Ginori porcelain !"

Reviewed on 14 Jun 2025

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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
9.2/10 Wonderful! (113 reviews)
"Fabulous location just outside the entrance to the main part of town. Property is stylish in an olde worlde way, perfect for relaxation."

Reviewed on 18 Apr 2025

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Hotel San Gregorio
See all 6,144 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.

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.

Popular places to visit

Palazzo Piccolomini

5/5(9 reviews)

You can study the exhibits at Palazzo Piccolomini, a museum with a storied past, during your holiday in Pienza. While you're here, you can savour the wineries.

Palazzo Piccolomini

Monastery of Sant'Anna in Camprena

You can find out about the history of Pienza with a visit to Monastery of Sant'Anna in Camprena. Discover the countryside and churches in this quaint area.

Monastery of Sant'Anna in Camprena

Piazza Pio II

After visiting Piazza Pio II, make a plan to see the other sights and activities in Pienza. While you're here, you can savour the wineries.

Piazza Pio II