Pienza Vacation Packages

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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.

Top Pienza Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Eurostars Florence Boutique
Grand Hotel Cavour
Bernini Palace
Palazzo Lorenzo Hotel Boutique & Spa
Art Atelier

The Annual Vacation Sale

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Things to do in and around Pienza

Pienza, a charming destination in Tuscany, offers a perfect blend of outdoor adventures and romantic experiences. Visitors can indulge in spa treatments, explore various attractions, and enjoy unique activities like vespa tours. The quaint atmosphere is ideal for leisurely strolls or relaxing at a country private club. Whether you're seeking relaxation or adventure, Pienza promises a memorable getaway filled with delightful experiences.

Shopping

Pienza offers charming shopping experiences with local stores like RI Crea RE, perfect for unique souvenirs. If you're up for a drive, visit Valdichiana Outlet Village, 19.3km away, for a variety of shops and entertainment, or Pinzi Pinzuti, located 22.5km from town, for more options.

Recreation

Experience the serene surroundings at the Chapel of Our Lady of Vitaleta, a countryPrivateClub offering luxury vibes just 3.2km from Pienza. Indulge in wellness and relaxation at the Terme di Chianciano spa, located 11.3km away, or rejuvenate at San Giovanni Terme Rapolano, a body treatment venue 24.1km from Pienza.

Adventure

Experience thrilling adventures in Pienza. Hit the slopes at Macinaie Ski Lift, 20.9km away, for skiing fun. Feel the adrenaline at the Siena Circuit karting track, located 30.6km from Pienza. For outdoor excitement, zip through the trees at Saltalbero Adventure Park, 24.1km away.

Nightlife

Pienza offers a charming nightlife with quaint wine bars and local eateries. Visit Enoteca di Pienza for exquisite Tuscan wines, and enjoy a cozy atmosphere. For a lively experience, head to La Bottega del Vino, where you can savour local cheeses and listen to traditional Italian music.

*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 Tuscan town, offers a romantic and entertaining getaway with its stunning piazzas, serene monasteries, and relaxing hot springs. Explore the beautiful villas and the historic centre, including the impressive Pienza Cathedral, while soaking in the picturesque Val d'Orcia scenery. Whether you're seeking cultural experiences or outdoor adventures, Pienza has something special for every traveller.

  • Pienza Cathedral: Experience the serene beauty of Pienza Cathedral, a stunning example of Renaissance architecture situated in the heart of Pienza. Its intricate design and cultural significance make it a must-visit for art and history enthusiasts.
  • Terme di Montepulciano Spa: Located 9.7km away, indulge in the therapeutic benefits of Terme di Montepulciano Spa. This natural hot spring offers a blissful escape for wellness and relaxation, surrounded by picturesque outdoor scenery.
  • Palazzo Ricci: Just 8.0km from Pienza, Palazzo Ricci is a historical academy that showcases rich cultural heritage. Stroll through its elegant halls and immerse yourself in the fascinating history of this remarkable building.

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 to Pienza during the low season (December to February) for more affordable options.
  • 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.

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Pienza Hotel Deals

Hotel Relais II Chiostro di Pienza

Hotel Relais II Chiostro di Pienza

4 out of 5
Corso Rossellino 26 Pienza SI
8.8/10 Excellent! (635 reviews)
A little tired, extremely clean, with an amazing staff

Reviewed on Jan 1, 2026

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
9.4/10 Exceptional! (134 reviews)
Super convenient location steps to the historic center. Possibly the only hotel with its own dedicated secure / covered parking. Well decorated and breakfast was great!

Reviewed on Oct 25, 2025

Hotel San Gregorio
Hotel Corsignano

Hotel Corsignano

4 out of 5
Via Della Madonnina 11 Pienza SI
Fully refundableReserve now, pay when you stay
The price is CA $146 per night from Mar 1 to Mar 2
CA $146
CA $171 total
Mar 1 - Mar 2
includes taxes & fees
9.4/10 Exceptional! (332 reviews)
Wonderful stay. Very welcoming staff and check in was quick and simple. Very convenient as parking provided. Room was spacious especially bathroom with great bathtub Breakfast was perfect

Reviewed on Nov 28, 2025

Hotel Corsignano
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.

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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.