Pienza Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

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
Fully refundableReserve now, pay when you stay
8.6/10 Excellent! (569 reviews)
Great Town, not so great hotel
"The hotel it's ok It's a former Franciscan Convent dating back to 13th century! Depending of the room.it will be room size. The best views you will get from the outside terrace where breakfast it's served Amazing views of Toscana The hotel it's located right in the middle of the town Pienza right ..."

Reviewed on 29 Jun, 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
9.4/10 Exceptional! (298 reviews)
"Second time visiting Great breakfast with Richard Ginori porcelain !"

Reviewed on 14 Jun, 2025

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Hotel Corsignano
Tenuta Santo Pietro
Tenuta Santo Pietro
Localita Santo Pietro 29, Pienza, SI
The price is S$282 per night from 10 Aug to 11 Aug
S$282
10 Aug - 11 Aug
includes taxes & fees
9.6/10 Exceptional! (109 reviews)
Family trip
"Beautiful place to be with family!"

Reviewed on 2 Jul, 2025

Tenuta Santo Pietro
See all 6,185 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.

Popular places to visit

Palazzo Borgia

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

Palazzo Borgia

What to do in Pienza

Pienza: Dairy Farm Tour with Pecorino Cheese Tasting

Pienza: Dairy Farm Tour with Pecorino Cheese Tasting

S$97
per adult
Pienza: Dairy Farm Tour with Pecorino Cheese Tasting
Passeggiando nell'uliveto: come nasce l'olio extrav d'oliva?

Passeggiando nell'uliveto: come nasce l'olio extrav d'oliva?

S$45
per adult
Passeggiando nell'uliveto: come nasce l'olio extrav d'oliva?
Val D'Orcia Dreaming!!

Val D'Orcia Dreaming!!

S$293
per adult
Val D'Orcia Dreaming!!
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.