Pienza Holidays

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Top Flight + Hotel Deals in Pienza

Price found within the past 48 hours. Click for updated prices.
Borgo Grondaie

Borgo Grondaie

3 out of 5
Save 100% on your flight
per person
2 May - 6 May
found 1 day ago
Return flight included
Dublin (DUB) to Florence (FLR)
9.6/10 Exceptional! (403 reviews)
Beautiful hotel and awesome location. Hotel is located at the edge of Siena central city. An easy walk to the city with the added benefit of being in a quiet location. We loved Siena! The grounds were beautiful as was the hotel and room. The room was a spacious apartment with a large bedroom full of windows overlooking the beautiful grounds. Also,a comfortable king bed with an attached living room and kitchen. We cooked in our room one night with the supplies from the large grocery store a short walk from the hotel. Dishes, utensils and cooking pans supplied in the room. The train and bus terminal were a short walk from the hotel for easy connections to other areas. We loved this hotel so much we extended our stay an extra day.

Reviewed on 12 Mar 2025

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Save 100% on your flight
per person
2 May - 6 May
found 1 day ago
Return flight included
Dublin (DUB) to Florence (FLR)
9.4/10 Exceptional! (76 reviews)
Absolutely beautiful property with very friendly and helpful staff. They really took care of us during our short stay

Reviewed on 20 Mar 2025

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Cortona Old Town
Save 100% on your flight
per person
2 May - 6 May
found 1 day ago
Return flight included
Dublin (DUB) to Florence (FLR)
10/10 Exceptional! (204 reviews)
The inside and outside is beautiful. It overlooks the town of Cortona. The staff were fantastic. They treated us like we were part of their own families.

Reviewed on 21 Nov 2024

The Sense Experience Resort

The Sense Experience Resort

5 out of 5
Save 100% on your flight
per person
2 May - 6 May
found 1 day ago
Return flight included
Dublin (DUB) to Florence (FLR)
9/10 Wonderful! (154 reviews)
A beautiful relaxing property with a staff that is exemplary. We didn’t want to leave!!

Reviewed on 25 Sep 2024

Villa Tolomei Hotel & Resort

Villa Tolomei Hotel & Resort

5 out of 5
Oltrarno
Save 100% on your flight
per person
2 May - 6 May
found 1 day ago
Return flight included
Dublin (DUB) to Florence (FLR)
9/10 Wonderful! (364 reviews)
Super location with views over the beautiful city of Florence! Super staff, Daniel you were a legend! Dinner was astonishing, fabulous food and service! You can walk to the city centre, downhill and flat, 20 minutes or so, definitely a taxi back, circa 12 Euro!

Reviewed on 19 Oct 2024

Top hotels in Pienza

Hotel Corsignano
Hotel Corsignano
4 out of 5
Via Della Madonnina 11, Pienza, SI
Fully refundableReserve now, pay when you stay
The price is €154 per night from 1 Apr to 2 Apr
€154
includes taxes & fees
1 Apr - 2 Apr
9.2/10 Wonderful! (276 reviews)
"Good service and breakfast."

Reviewed on 19 Mar 2025

Hotel Corsignano
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
The price is €73 per night from 7 Apr to 8 Apr
€73
includes taxes & fees
7 Apr - 8 Apr
8.6/10 Excellent! (544 reviews)
Good stay
"Needed an extra night and got a room through Hotels.com. Was there for a wedding. The room was small but the location was where I wanted to be and the breakfast was very good."

Reviewed on 29 Sep 2024

Hotel Relais II Chiostro di Pienza
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 €125 per night from 26 Mar to 27 Mar
€125
includes taxes & fees
26 Mar - 27 Mar
9.2/10 Wonderful! (108 reviews)
"Very nice staff, great service, super clean. Will stay again."

Reviewed on 11 Apr 2024

Hotel San Gregorio
See all 6,037 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 from €439 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

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

Pienza Cathedral

4.5/5(19 reviews)

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

€95
per adult
82% of travellers recommend
Tuscany Wine & Hills from Siena
Private Cooking class in Val d'Orcia

Personal Chef - Cooking class at your villa

€150
per adult
Personal Chef - Cooking class at your villa
Pienza & Montepulciano Small Group Tour from Siena

Pienza & Montepulciano Small Group Tour from Siena

€180
per adult
Pienza & Montepulciano Small Group Tour from Siena
See all activities in Pienza
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.