Pienza Vacations from $647

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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.
EXE Toscana

EXE Toscana

4 out of 5
Lucca Historical Center
per person
Apr 28 - May 2
found 1 day ago
Roundtrip flight included
New York (NYC) to Florence (FLR)
8.4/10 Very Good! (774 reviews)
Personale professionale e gentilissimo.

Reviewed on Jan 27, 2025

Aurum Firenze

Aurum Firenze

4 out of 5
Santa Maria Novella
per person
May 9 - May 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,001 reviews)
Service is excellent. The location makes it very easy to maneuver your needs, pharmacy, restaurants, gelato shops, train terminal all in its close surroundings. Rooms are spacious; service 24/7.

Reviewed on Jan 9, 2025

Grand Hotel Cavour

Grand Hotel Cavour

4 out of 5
Duomo
per person
May 9 - May 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.2/10 Wonderful! (1,002 reviews)
I wasn’t told my room was upgraded.

Reviewed on Mar 10, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Santa Croce
Save 100% on your flight
per person
May 25 - May 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
8/10 Very Good! (1,003 reviews)
The location was great. As was the check in. The room had an unpleasant, sour septic smell. Quite similar to septic “burps” we experienced in Rome. The room was modern with a generous sized bathroom. The pillows were quite flat, there was not enough hot water for two showers, and the breakfast was mediocre.

Reviewed on Mar 11, 2025

Palazzo Firenze by Baglioni Hotels & Resorts

Palazzo Firenze by Baglioni Hotels & Resorts

5 out of 5
Santa Croce
Save 100% on your flight
per person
May 18 - May 23
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.4/10 Exceptional! (222 reviews)
During our recent visit to Florence, we had the pleasure of staying at Palazzo Firenze, and it was absolutely perfect. The staff provided exceptional service and had great knowledge of the area. Our room was spotless and incredibly comfortable. The hotel's location was ideal for sightseeing and dining. We couldn’t have chosen a better place to stay and would definitely return.

Reviewed on Feb 18, 2025

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

Ready to book your vacation to Pienza?

 

Choose your dates

Pienza Hotel Deals

Hotel Relais II Chiostro di Pienza
Hotel Relais II Chiostro di Pienza
4 out of 5
Corso Rossellino 26, Pienza, SI
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 Sep 29, 2024

Get rates
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
The price is $131 per night from Mar 23 to Mar 24
$131
includes taxes & fees
$113 per night
Mar 23 - Mar 24
9.2/10 Wonderful! (275 reviews)
"Very good hotel, at a very good location. The hotel looks great and is managed very professionally. A few minutes away from the historic walled city. Hope to stay there again when visiting the amazing Tuscan wine country."

Reviewed on Mar 10, 2025

Hotel Corsignano
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 $137 per night from Mar 17 to Mar 18
$137
includes taxes & fees
$119 per night
Mar 17 - Mar 18
9.2/10 Wonderful! (111 reviews)
"Very nice staff, great service, super clean. Will stay again."

Reviewed on Apr 11, 2024

Hotel San Gregorio
See all 6,070 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Pienza vacation package cost?
You can snap up a vacation package to this popular destination from $647 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.

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

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

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

What to do in Pienza

Montalcino, Pienza & Montepulciano Wine Tour From Siena

Tuscany Wine & Hills from Siena

$99
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

$156
per adult
Personal Chef - Cooking class at your villa
Pienza & Montepulciano Small Group Tour from Siena

Pienza & Montepulciano Small Group Tour from Siena

$187
per adult
Pienza & Montepulciano Small Group Tour from Siena
See all activities in Pienza

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