Pienza Vacations from $1,105

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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 La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

Historic Centre of Florence
$1,105
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9/10 Wonderful! (1,002 reviews)
Aurum Firenze

Aurum Firenze

Historic Centre of Florence
$1,374
per person
Oct 20 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.4/10 Good! (1,011 reviews)
Chambre plus étroite, mais propre. Staff sympa. Notre douche coulait dans la salle de bain et le jet traversait le haut de la porte. Nous n’avons pas aimé le petit buffet déjeuner, manque de fraîcheur (pain/croissant). Cependant, une belle vue pour le petit déjeuner.

Reviewed on Aug 7, 2026

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

$2,498
per person
Sep 16 - Sep 19
found 8 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (155 reviews)
The place it’s an Amazing. Very clean. Is more beautiful than the pictures.

Reviewed on Aug 2, 2026

Il Leccio Luxury Resort

Il Leccio Luxury Resort

Save 100% on your flight
$3,495
per person
Sep 13 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Pisa (PSA)
8.8/10 Excellent! (12 reviews)
Great location, rooms, pool and food

Reviewed on Aug 31, 2025

Aurum Uffizi

Aurum Uffizi

Historic Centre of Florence
$1,188
per person
Sep 10 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
7.6/10 Good! (1,004 reviews)
The room was clean and air conditioning worked well for the size of room. However, the room was a little small for a family of four. The location was one of the best aspects of the hotel: it was right in the historic centre and near all the attractions. Staff were also very helpful, promptly responding to our requests.

Reviewed on Aug 2, 2026

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Stay near popular Pienza attractions

A historic church with a bell tower, arched windows, and a central dome.

Pienza Cathedral

9.4/10 (460 reviews)
Pope Pius II's Renaissance masterpiece showcases harmonious Gothic elements and luminous three-nave design. Arrive early to admire the 15th-century Sienese paintings and enjoy panoramic Tuscan views from the corridor.
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Rolling green hills, a historic town with red-roofed buildings, and a prominent church tower.

Historic Centre of Pienza

9.6/10 (42 reviews)
Pienza's Historic Centre showcases Pope Pius II's Renaissance ideal city vision with harmonious architecture. Explore cobblestone streets, the Cathedral and Palazzo Piccolomini, and sample the town's famous pecorino cheese.
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Palazzo Piccolomini

9.4/10 (199 reviews)
This Renaissance masterpiece was Pope Pius II's summer residence, designed by Bernardo Rossellino. From its hanging gardens, savor breathtaking panoramic views across the Val d'Orcia's rolling Tuscan landscape.
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Pieve di Corsignano

9.0/10 (17 reviews)
This 10th-century Romanesque church features a circular bell tower and Pope Pius II's baptismal font. Inside, soft light illuminates ancient stone carvings across its three-naved interior.
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Monastery of Sant'Anna in Camprena

This former monastery in the Tuscan hills showcases remarkable Renaissance frescoes in a tranquil setting. Savor authentic regional cuisine while staying overnight in the historic stone buildings.
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Palazzo Borgia

8.8/10 (21 reviews)
This Renaissance palace houses the Museo Diocesano with masterpieces by Lorenzetti and Signorelli. Admire 12th-century crucifixes and medieval art while exploring the former residence of Cardinal Rodrigo Borgia.
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Piazza Pio II

9.2/10 (44 reviews)
This Renaissance masterpiece, designed by Bernardo Rossellino in 1459, showcases perfect architectural harmony at Pienza's heart. Explore the cathedral's artworks and enjoy sweeping Tuscan views from the elegant terrace.
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Enoteca Di Ghino

10.0/10 (1 review)
This intimate wine shop in Pienza's historic center showcases 2,000 carefully curated Italian and international labels. Let the knowledgeable staff guide you through tastings that perfectly complement Tuscan cuisine.
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What to do in Pienza

Tasting Tour in One of The Most Beautiful Cellars in the World

Tasting Tour in One of The Most Beautiful Cellars in the World

$38
per adult
100% of travellers recommend
Tasting Tour in One of The Most Beautiful Cellars in the World
Montalcino: Guided Winery Tour and Wine Tasting

Montalcino: Guided Winery Tour and Wine Tasting

$51
per adult
Montalcino: Guided Winery Tour and Wine Tasting
Montepulciano Wine Tasting in the Tuscan Countryside

Montepulciano Wine Tasting in the Tuscan Countryside

$28
per adult
Montepulciano Wine Tasting in the Tuscan Countryside
See all activities in Pienza

Pienza Hotel Deals

Hotel Corsignano

Hotel Corsignano

Via Della Madonnina 11 Pienza SI
Fully refundableReserve now, pay when you stay
$166 nightly
$190 total
Aug 9 - Aug 10
Total with taxes and fees
Hotel Corsignano
Hotel San Gregorio

Hotel San Gregorio

Via Della Madonnina 4 Pienza SI
$230 nightly
$260 total
Aug 8 - Aug 9
Total with taxes and fees
Hotel San Gregorio
Agriturismo Il Macchione

Agriturismo Il Macchione

S.P. 71 Per S. Anna in Camprena Pienza SI
$202 nightly
$227 total
Aug 18 - Aug 19
Total with taxes and fees
9.6/10 Exceptional! (71 reviews)
"We had an amazing time staying at this property: the staff were super helpful, going beyond what was expected to accommodate our late arrival. The room was very clean and cozy looking, the views surrounding the property were breathtaking, we couldn’t believe our eyes. The view of the property were ..."

Reviewed on Jun 17, 2026

Agriturismo Il Macchione
See all 6,076 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

Things to do in and around Pienza

Pienza, nestled in Tuscany, is perfect for outdoor and romantic getaways, offering a range of activities for visitors. Enjoy rejuvenating spa treatments, unwind at a private country club, or embark on delightful wine tours. The picturesque picnic areas provide a lovely setting for relaxation, while the charm of the town invites exploration. Don't miss the opportunity to experience the unique culture and scenic beauty of Pienza during your visit.

Shopping

For unique souvenirs, visit RI Crea RE in Pienza for local crafts. If you're up for a drive, Valdichiana Outlet Village, located 12 miles away, offers a variety of brands and family-friendly entertainment. Pinzi Pinzuti, 14 miles away, is another charming spot for gifts.

Recreation

Experience luxury at the Chapel of our Lady of Vitaleta, a serene country club just 2 miles from Pienza. Unwind at Terme di Chianciano, a soothing spa 7 miles away, or indulge in rejuvenating treatments at San Giovanni Terme Rapolano, located 15 miles from Pienza.

Adventure

The Macinaie Ski Lift, located 13 miles from Pienza, offers thrilling skiing experiences amidst stunning alpine scenery. For adrenaline-pumping karting, visit the Siena Circuit, 19 miles away. Alternatively, the Saltalbero Adventure Park, 15 miles from Pienza, features exciting zip lines and rope courses for an outdoor adventure.

Nightlife

Pienza's nightlife offers a charming blend of cozy wine bars and local taverns. Visit Bar di Pienza for a delightful aperitivo and enjoy the warm atmosphere. For a more lively scene, head to La Bottega di Pienza, where you can savor local wines and mingle with friendly locals.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Pienza

Pienza, a charming town in Tuscany, is perfect for outdoor and romantic getaways. Explore the stunning piazza, visit the historic monastery, or relax in natural hot springs. This destination offers a rich cultural experience with attractions like the Pienza Cathedral and various outdoor activities. Whether you’re on a trip to Pienza for its scenic beauty or unique local experiences, you'll find plenty to enjoy in this picturesque town.

  • Pienza Cathedral: Nestled in the heart of Pienza, this stunning cathedral showcases Renaissance architecture and offers a serene atmosphere. Explore its beautifully adorned interior and soak in the cultural vibes that make it a must-visit.
  • Piazza Grande: Located 5 miles from Pienza, Piazza Grande is a bustling square that embodies the essence of local life. Surrounded by charming cafes and shops, it’s the perfect spot to experience the vibrant culture and city vibes of the region.
  • Terme di Montepulciano Spa: Just 6 miles away, this luxurious hot spring offers a tranquil retreat. Enjoy wellness and relaxation in beautiful outdoor settings, making it an ideal place to unwind and rejuvenate.

Best time to go to Pienza

The best time to visit Pienza can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Pienza falls in July and August. August has slightly high visitor numbers and sunny weather. The coolest average temperature in Pienza falls in January, visitor numbers are slightly low and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January39.4°F (4.1°C)Light RainMostly SunnySlightly LowSlightly Low
February40.6°F (4.8°C)Light RainMostly SunnyAverageSlightly Low
March45.0°F (7.2°C)Light RainMostly SunnyAverageAverage
April50.9°F (10.5°C)Light RainMostly SunnySlightly HighAverage
May57.4°F (14.1°C)Light RainMostly SunnyAverageAverage
June66.7°F (19.3°C)Light RainSunnyAverageSlightly High
July73.0°F (22.8°C)No RainSunnyAverageSlightly High
August73.0°F (22.8°C)No RainSunnySlightly HighSlightly High
September64.8°F (18.2°C)Light RainMostly SunnySlightly HighAverage
October56.7°F (13.7°C)Light RainMostly SunnyAverageAverage
November48.6°F (9.2°C)Light RainMostly SunnySlightly LowAverage
December42.1°F (5.6°C)Light RainMostly SunnySlightly LowSlightly Low

Tips to save on your trip to Pienza

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling during the off-peak season (typically December to February) for more affordable package holidays to Pienza.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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 $1,105 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.

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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.