Pienza Holidays

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Top Flight + Hotel Deals in Pienza

Price found within the past 48 hours. Click for updated prices.
Hotel Miceli - Civico 50

Hotel Miceli - Civico 50

3 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
26 Sept - 29 Sept
found 18 hours ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
8.8/10 Excellent! (185 reviews)
There was no staff on-site when we arrived, but we had been in touch with the hotel via WhatsApp all day, and they were super helpful and friendly! Entering the building was very easy, but the 3-person elevator was just a little squished. The room was as expected - the only downside was that the shower was only cold water (after running it for a few minutes) and the sink in the bathroom was only hot water! The room was warm when we entered, but we turned the air conditioning up and it was perfect by the time we arrived back for bed. All-in-all, it was a good stay overnight!

Reviewed on 22 Jun 2025

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
26 Sept - 30 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
7.6/10 Good! (1,012 reviews)
Walking distance to all attractions and train station. Room little small but ok , loved the balcony for breakfast that was awesome. Very friendly staff.

Reviewed on 2 Aug 2025

LHP River Club

LHP River Club

5 out of 5
Santa Croce
Save 100% on your flight
per person
26 Sept - 30 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
No reviews
Villa Tolomei Hotel & Resort

Villa Tolomei Hotel & Resort

5 out of 5
Oltrarno
Save 100% on your flight
per person
26 Sept - 30 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
8.8/10 Excellent! (387 reviews)
Great place to stay near Florence, it’s quite and relaxing. The pool is great.

Reviewed on 31 Jul 2025

Grand Hotel Cavour

Grand Hotel Cavour

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
26 Sept - 30 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
9.2/10 Wonderful! (1,005 reviews)
Walkable to main sites.

Reviewed on 3 Aug 2025

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! (577 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 31 Jul 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! (301 reviews)
"All 1st class. Food excellent"

Reviewed on 20 Jul 2025

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Hotel Corsignano
Tenuta Santo Pietro

Tenuta Santo Pietro

Localita Santo Pietro 29, Pienza, SI
The price is €228 per night from 11 Aug to 12 Aug
€228
11 Aug - 12 Aug
includes taxes & fees
9.6/10 Exceptional! (111 reviews)
Family trip
"Beautiful place to be with family!"

Reviewed on 2 Jul 2025

Tenuta Santo Pietro
See all 6,187 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 featuring a church or cathedral, religious aspects and heritage elements

Pienza Cathedral

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

Pienza Cathedral

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

Montalcino, Pienza & Montepulciano Wine Tour From Siena

Tuscany Wine & Hills from Siena

€129
per adult
82% of travellers recommend
Tuscany Wine & Hills from Siena
Wine Tasting in Toscana with Priority Access

Wine Tasting in Toscana with Priority Access

€15
per adult
Wine Tasting in Toscana with Priority Access
Chianciano Terme: Sensory Spa Admission Ticket

Chianciano Terme: Sensory Spa Admission Ticket

€45
per adult
Chianciano Terme: Sensory Spa Admission Ticket
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 from €458 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.