Pienza Holidays from £427

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Your Pienza Holiday

Get ready to experience Pienza in your own style with a custom Pienza holiday package! Uncovering the charms of this captivating city is made simpler with a base in a neighbourhood 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 organising your ultimate holiday to Pienza now.

Top Pienza Flight + Hotel Deals

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

Hotel Centro

Historic Centre of Florence
Save 100% on your flight
£427
per person
19 Oct - 23 Oct
found 1 day ago
Return flight included
London (LON) to Florence (FLR)
8.2/10 Very good! (62 reviews)
Villa Cora

Villa Cora

Oltrarno
£1,114
per person
24 Oct - 28 Oct
found 19 hours ago
Return flight included
London (LGW) to Florence (FLR)
9.8/10 Exceptional! (482 reviews)
EXE Toscana

EXE Toscana

Mugnano
Save 100% on your flight
£986
per person
26 Oct - 31 Oct
found 1 day ago
Return direct flight included
London (LHR) to Florence (FLR)
8.4/10 Very good! (853 reviews)
The hotel is located very near the autostrade and outside the walled city. Access is easy and direct. Staff were multi lingual and friendly. English was not a problem. Parking is free. Breakfast is served as a buffet and you do need to notify if you intend to partake. It is 13euros. There is a good variety, but it is the same every day. There is an espresso/coffee machine. Nothing available to order. Amenities. There aren’t any (like fitness room or pool). There are meeting rooms up from the lobby. The restaurant isn’t open beyond breakfast and they only offer the buffet. The bar is only open weekdays in the evening. There is a supermarket next door and a McDonald’s around the corner, both easy walking distance. A bit further are a couple of sit-down restaurants and a very good pizzeria. There are more pizzerias here than Starbucks in Seattle! We would stay there again. The lack of amenities isn’t important to us.

Reviewed on 2 Aug 2026

Palace Hotel

Palace Hotel

Marco Polo
Save 100% on your flight
£560
per person
26 Oct - 31 Oct
found 1 day ago
Return direct flight included
London (LHR) to Florence (FLR)
9/10 Wonderful! (139 reviews)
Dimora Palanca Boutique & SPA

Dimora Palanca Boutique & SPA

Historic Centre of Florence
Save 100% on your flight
£896
per person
15 Oct - 20 Oct
found 24 hours ago
Return flight included
London (LGW) to Florence (FLR)
9.2/10 Wonderful! (69 reviews)
The accommodation very much complimented our wonderful experience and love for Florence. Our room, the connected amenities and the wonderful attentive service made our trip very memorable.

Reviewed on 7 Sept 2026

Things to do in and around Pienza

Pienza offers a charming blend of outdoor activities and romantic experiences, making it an ideal destination for visitors. Enjoy rejuvenating spa treatments, indulge in body therapies, and explore the serene countryside at private clubs. As you embark on your tourist journey, immerse yourself in the local culture and discover the delightful activities that Pienza has to offer, ensuring a memorable holiday in this picturesque Tuscan town.

Shopping

Pienza offers charming local shops like RI Crea RE for unique gifts. If you're up for a drive, Valdichiana Outlet Village, 19.3km away, features a variety of brands and family-friendly entertainment. Pinzi Pinzuti, 22.5km from Pienza, is also worth a visit for distinctive finds.

Recreation

Terme di Chianciano offers a tranquil spa experience, perfect for relaxation and rejuvenation, located 11.3km from Pienza. For sports enthusiasts, Golf Club Valdichiana, 19.3km away, provides a stunning golf course amidst beautiful landscapes. Families can enjoy the Parco Piscine Capenti Outdoor Pool, situated 25.7km from Pienza.

Adventure

Experience thrilling fun at Tavernelle Aquatic Park, located 37.0km from Pienza, featuring water slides and family entertainment. For winter sports, visit Macinaie Ski Lift, 20.9km away, offering skiing adventures. Alternatively, race at the Siena Circuit, a karting venue 30.6km from Pienza, perfect for adrenaline seekers.

Nightlife

Pienza's nightlife is charmingly laid-back, with quaint wine bars like La Bottega di Pienza offering local vintages. For a lively evening, enjoy live music at the historic Caffè degli Artisti, where you can soak in the vibrant atmosphere and mingle with 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, nestled in Tuscany, offers a delightful blend of outdoor activities and romantic experiences. Visitors can explore charming piazzas, historic monasteries, and refreshing hot springs. The town is perfect for those seeking culture and nature, with must-see attractions like the Pienza Cathedral and the enchanting landscapes of Pienza Tuscany. Whether you’re after relaxation or adventure, Pienza promises a memorable getaway.

  • Pienza Cathedral: Nestled in the heart of Pienza, this stunning cathedral showcases remarkable Renaissance architecture and offers a serene atmosphere. Its intricate interior and beautiful artworks create a profound cultural experience.
  • Terme di Montepulciano Spa: Located 9.7km from Pienza, this enchanting hot spring spa provides a perfect escape for wellness and relaxation. Enjoy the soothing thermal waters amidst picturesque outdoor settings, ideal for rejuvenating both body and mind.
  • Palazzo Piccolomini: This historic palace in Pienza embodies Renaissance elegance with its beautiful gardens and splendid architecture. It offers a glimpse into the region's rich history and cultural heritage, making it a must-visit.

Best time to go to Pienza

The best time to visit Pienza is dependent on what kind of holiday you are seeking. July and August are its hottest month on average. At the time of August, visitor numbers are slightly high and weather is sunny. January is its coolest month on average. At this time, 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

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Pienza.
  • 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.

Pienza Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Population
1,250
Max Temp Winter
10ºC
Max Temp Summer
29ºC
Top Sights
Pienza Cathedral, Piscine Termali Theia and Terme di Montepulciano Spa

Top hotels in Pienza

Hotel San Gregorio

Hotel San Gregorio

Via Della Madonnina 4 Pienza SI
Fully refundableReserve now, pay when you stay
£170
10 Oct - 11 Oct
includes taxes & fees
Hotel San Gregorio
Hotel Corsignano

Hotel Corsignano

Via Della Madonnina 11 Pienza SI
Fully refundableReserve now, pay when you stay
£151
13 Sept - 14 Sept
includes taxes & fees
9.4/10 Exceptional! (381 reviews)
"My husband and I had an absolutely wonderful experience at Hotel Corsignano. From beginning to end, the staff went above and beyond to make us feel welcome and cared for. When we arrived a little later than expected, they were genuinely concerned about us and even made sure to save a parking spot ..."

Reviewed on 12 Sept 2026

Hotel Corsignano
Agriturismo Il Macchione

Agriturismo Il Macchione

S.P. 71 Per S. Anna in Camprena Pienza SI
£158
9 Oct - 10 Oct
includes taxes & fees
9.6/10 Exceptional! (73 reviews)
"During our 2.5 week trip to Tuscany, we stayed 4 nights. True hospitality. Vera served our breakfast daily and wanted to help in any way possible."

Reviewed on 4 Sept 2026

Agriturismo Il Macchione
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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, savour breathtaking panoramic views across the Val d'Orcia's rolling Tuscan landscape.
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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. Savour authentic regional cuisine while staying overnight in the historic stone buildings.
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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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Palazzo Vescovile

9.0/10 (12 reviews)
The Palazzo Vescovile showcases a captivating collection of religious art from the 14th-15th centuries. Admire Pietro Lorenzetti's Madonna di Monticchiello while exploring eleven rooms filled with sacred treasures.
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Artemisia Gallery

8.8/10 (9 reviews)
You can study the exhibits at Artemisia Gallery, a museum with a story of its own, during your trip to Pienza. While you're here, you can savour the wineries.
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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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What to do in Pienza

3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch

From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch

£72
per adult
98% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
Montepulciano Gran Tour

Montepulciano Gran Tour

£13
per adult
Montepulciano Gran Tour
Montalcino: Guided Winery Tour and Wine Tasting

Montalcino: Guided Winery Tour and Wine Tasting

£39
per adult
Montalcino: Guided Winery Tour and Wine Tasting
See all activities in Pienza

Frequently asked questions

Why should I book my Pienza holiday with Expedia?
With great-value airfares, car hire and accommodation choices all in one convenient place, Expedia makes planning your Pienza adventure a piece of cake. Plus, we can help you bundle your bookings into a package holiday so you can enjoy even more savings. Choose from fantastic escapes, add flights and/or a car hire (and maybe even some fun tours!) and score incredible prices. Want to change your plans? Expedia has a flexible cancellation policy for many reservations. To find out more, visit our Customer Service Portal link.
When is the best time of year to holiday in Pienza?
Pienza draws the crowds in February, May and July. If you want a more relaxed escape, visit in March, November and December. To give you an idea of what type of weather to expect, the daytime average temperature in January, the coolest month in Pienza, is 4ºC. The warmest time here is July, when temperatures reach an average of 22ºC.
What is the top hotel for my holiday in Pienza?
Relax in comfort in Pienza by choosing Hotel Athena as your gateway to exploration.
How do I get a cheap holiday to Pienza?
One of the easiest ways to save money (and time) is to bundle your bookings with Expedia. Flights, hire cars, hotels and activities — we've got them all. Pick the combination that best fits you and see your savings grow. We know holidays are never a one-size-fits-all. That's why Expedia offers over 400 air carriers and 321,000 properties across the globe, so you can customise your Pienza holiday your way. Learn more about how you can save money on your holiday when you combine your hotel and flight bookings with Expedia.
What should I do on my Pienza holiday?
With must-see tourist attractions such as Pienza Cathedral and Palazzo Piccolomini, a holiday in Pienza promises lots of exciting places to visit. Tenuta Greppo Franco Biondi Santi and Chapel of our Lady of Vitaleta are a couple of other sights worth exploring.
What is the best area to stay in when on holiday in Pienza?
There's so much to do in Pienza, so stay close to its best sights and allow yourself more time sightseeing. Pienza Cathedral is one place to put on your to-do list.
Do I need a visa for my Pienza holiday?
Visa requirements for Pienza vary depending on your nationality and reason for your visit. Check official government websites to determine if you need a visa for your holiday. This is also a good place to find the most up-to-date information, including details about application procedures or any supporting documentation you might need. Research your visa requirements well in advance to ensure a travel experience that's hassle free. Finally, check to see that your passport is valid for a further six months from the date of your return.
What should I wear on my Pienza holiday?
Although everyone's style is different, it can be helpful to have some guidelines for what type of clothes to wear on your holiday in Pienza. Consider searching style blogs before you leave to get inspiration for local fashion trends. Be sure to look at the local weather forecast so you can pack your bags accordingly. The warmest time of year in Pienza is July, with average daily temperatures of 22ºC. If you're on holiday during the coolest month of January, the mercury averages 4ºC during the day.
What does an Expedia Pienza holiday include?
Flights, hotels and hire cars — we have them covered. With Expedia, you can create your Pienza travel package the way you like it. All you have to do is determine exactly what you need. Once you've made your booking, why not add extras like activities and experiences? The more you bundle, the bigger the savings! Villas and apartments are a few popular property types in Pienza. No matter your preference or size of your group, you can count on Expedia for the freedom and flexibility to customise your next dream escape.
Does Expedia offer Book Now, Pay Later Pienza holidays?
Expedia has partnered with online lender Klarna to make your next break easier on your bank balance. Paying by instalment means you can spread the costs of your next big holiday, leaving you with more money to spend while you're travelling. Klarna has several payment plans to choose from, so you're sure to find something that fits into your budget. Consider these flexible payment options:
  • Pay monthly holidays: Realise your holiday dreams sooner with Klarna's easy payment plans. If paying bite-sized amounts each month sounds right for you, choose this option at checkout.
  • No-deposit holidays: If not paying ahead of time for your trip makes clicking that "book now" button more stress-free, consider a no-deposit holiday plan with Klarna so that you can Book Now, Pay Later!
Can I choose my airline with a Pienza Expedia holiday?
With a holiday package, you're the one in charge. Whether you're hoping to fly to Pienza in coach or business class, simply select from the available airline options. Expedia has access to over 400 airline partners across the world.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.