Pienza Vacations from $748

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Your Pienza Vacation

Get ready to experience Pienza in your own style with a custom Pienza vacation package! Uncovering the charms of this captivating city is made simpler with a base in a neighborhood such as Macciano, which is great for walking, among other things. If sightseeing is on the to-do list during your trip to Pienza, visit big attractions like Pienza Cathedral, Palazzo Piccolomini and Chapel of our Lady of Vitaleta. Check out Expedia's wide range of travel options and start organizing your ultimate vacation to Pienza now.

The Latest Pienza vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Caravaggio

Hotel Caravaggio

3 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Florence (FLR)
8.8/10 Excellent! (1,004 reviews)
Wonderful stay - thank you!

Reviewed on Jul 7, 2025

Hotel Balestri

Hotel Balestri

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Florence (FLR)
9.2/10 Wonderful! (951 reviews)
Service was top notch. We had to wait 10 minutes for our room to be ready but they were great about everything and accommodating an early morning checkout with bag breakfasts for us. Location is also great next to the river and near major attractions in the city.

Reviewed on Jul 3, 2025

Hotel Ville sull'Arno

Hotel Ville sull'Arno

5 out of 5
Campo di Marte
Save 100% on your flight
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Florence (FLR)
9.6/10 Exceptional! (728 reviews)
Nice property. Decent room, but pay attention to room choice. My room, a suite, only had one small window overlooking the river. Some of the staff members are fantastic and others not. While marketed as a 5 star hotel, it is a mid 4 star hotel. While it has parking, it can only accommodate a few cars and street parking is rough. I had some day trips to do so parking for a rental was important. Otherwise I would have stayed in town center.

Reviewed on May 14, 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
Sep 22 - Sep 29
found 14 hours ago
Roundtrip flight included
New York (NYC) to Florence (FLR)
10/10 Exceptional! (212 reviews)
Amazing hotel, a must stay if visiting Cortona..best hotel in Tuscany

Reviewed on Jul 5, 2025

Hotel Bencista

Hotel Bencista

3 out of 5
Save 100% on your flight
per person
Aug 22 - Aug 27
found 15 hours ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
7.2/10 Good! (12 reviews)
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Discover the most popular places to visit in Pienza

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

Pienza Cathedral

5/5(131 reviews)

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

Pienza Cathedral

Palazzo Piccolomini

5/5(80 reviews)

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

Palazzo Piccolomini

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 savor the wineries.

Piazza Pio II

What to do in Pienza

Pienza: Dairy Farm Tour with Pecorino Cheese Tasting

Pienza: Dairy Farm Tour with Pecorino Cheese Tasting

$75
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?

$35
per adult
Passeggiando nell'uliveto: come nasce l'olio extrav d'oliva?
Val D'Orcia Dreaming!!

Val D'Orcia Dreaming!!

$226
per adult
Val D'Orcia Dreaming!!
See all activities in Pienza

Pienza Hotel Deals

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
$86 nightly
The price is $102 total per night from Jul 9 to Jul 10
$102 total
Jul 9 - Jul 10
Total includes taxes and fees
8.6/10 Excellent! (568 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 Jun 29, 2025

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
$161 nightly
The price is $184 total per night from Aug 3 to Aug 4
$184 total
Aug 3 - Aug 4
Total includes taxes and fees
9.4/10 Exceptional! (298 reviews)
"Second time visiting Great breakfast with Richard Ginori porcelain !"

Reviewed on Jun 14, 2025

Hotel Corsignano
Tenuta Santo Pietro
Tenuta Santo Pietro
Localita Santo Pietro 29, Pienza, SI
$196 nightly
The price is $221 total per night from Aug 7 to Aug 8
$221 total
Aug 7 - Aug 8
Total includes taxes and fees
9.6/10 Exceptional! (109 reviews)
Family trip
"Beautiful place to be with family!"

Reviewed on Jul 2, 2025

Tenuta Santo Pietro
See all 6,177 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.

Find the Best Pienza Vacation Packages

Pienza Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Population
1,250
Max Temp Winter
50ºF
Max Temp Summer
85ºF
Top Sights
Pienza Cathedral, Terme di Montepulciano Spa and Piscine Termali Theia

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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 from $748 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?
If you're looking to score a cheap Pienza vacation package, consider traveling in March, November and December. You'll usually find lower rates on airfares and hotels during these months --- perfect for a budget-friendly getaway.
How many days is enough for Pienza?
Typically, a handful of days is enough to visit the major attractions during your Pienza vacation. But if you want to have more time to rest or go on day trips, consider extending your trip.
Is it worth booking a vacation package to Pienza?
Well known for its views, hiking and festivals, a Pienza vacation is a hit with all kinds of visitors. Be sure to check out major sights like Pienza Cathedral and Palazzo Piccolomini, and consider renting a car for day trips to discover even more.
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: What you plan to do in Pienza and your favorite season will help you decide when to go.
  2. Plan your budget wisely: In addition to the cost of your hotel, you'll need to consider other expenses too. These include flights, food and transportation. Also, set aside a little extra for unexpected expenses that may crop up during your trip to Pienza.
  3. Use Expedia's trip planning tool to explore Pienza: Research every part of your trip to Pienza with this comprehensive planner. Invite friends or family to collaborate on a group getaway, search for hotels or things to do and make bookings.
  4. Determine how many days away: Start by making a list of all the sights and activities you'd like to experience in Pienza. Then, estimate how long you'll need for each, as well as any travel time.
  5. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to pick a Pienza vacation package that brings all your bookings together.
  6. Book any day trips or activities: Here's the fun part --- locking in everything you want to do and see. Check out some of the exciting things to do in Pienza and reserve your tickets early to save time (and maybe some spending money too!).

Does Expedia offer Book Now, Pay Later Pienza vacation packages?
If you're anything like us, you love traveling but don't love the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the cost of your Pienza vacation over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.