Pienza Trips (flight + hotel)

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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
Fully refundableReserve now, pay when you stay
8.6/10 Excellent! (578 reviews)
"Loved this hotel - great location. Really quiet despite such a central location. Yes rooms are not super modern but they reflect the history of the building. Great pool and breakfast on the terrace."

Reviewed on Jul 31, 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! (302 reviews)
"All 1st class. Food excellent"

Reviewed on Jul 20, 2025

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Hotel Corsignano
Tenuta Santo Pietro

Tenuta Santo Pietro

Localita Santo Pietro 29, Pienza, SI
The price is P13,547 per night from Aug 21 to Aug 22
P13,547
P15,168 total
Aug 21 - Aug 22
includes taxes & fees
9.6/10 Exceptional! (111 reviews)
Family trip
"Beautiful place to be with family!"

Reviewed on Jul 2, 2025

Tenuta Santo Pietro
See all 6,190 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

Cathedral of Pienza showing religious aspects, heritage elements and a church or cathedral

Pienza Cathedral

Admire the arresting Renaissance façade and the interior Gothic décor of this 15th-century cathedral commissioned by Pope Pius II.

Pienza Cathedral

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

Chiesa di San Francesco

You can find out about the history of Pienza with a visit to Chiesa di San Francesco. Discover the countryside and churches in this quaint area.

Chiesa di San Francesco

What to do in Pienza

Brunello di Montalcino small-group Wine Tour

Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena

P12,130
per adult
100% of travellers recommend
Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena
Val d'Orcia Brunello Wine Tour with Montalcino and Montepulciano

Val d'Orcia Brunello Wine Tour with Montalcino and Montepulciano

P15,432
per adult
100% of travellers recommend
Val d'Orcia Brunello Wine Tour with Montalcino and Montepulciano
Chianciano Terme: Theia Thermal Pools Entrance Ticket

Chianciano Terme: Theia Thermal Pools Entrance Ticket

P3,033
per adult
80% of travellers recommend
Chianciano Terme: Theia Thermal Pools Entrance Ticket
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Frequently asked questions

How much does a Pienza vacation package cost?
You can snap up a vacation package to this popular destination 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.

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