Pienza Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Top Flight + Hotel Deals in Pienza

Price found within the past 48 hours. Click for updated prices.
Eurostars Florence Boutique

Eurostars Florence Boutique

Historic Centre of Florence
€576
per person
27 Oct - 31 Oct
just found
Return direct flight included
Dublin (DUB) to Florence (FLR)
8.6/10 Excellent! (500 reviews)
mattresses were impossible to sleep on

Reviewed on 14 Sept 2026

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

Historic Centre of Florence
€1,397
per person
25 Oct - 30 Oct
found 10 hours ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
9.6/10 Exceptional! (592 reviews)
Great location. We suggest taking the river down to the city center every day. The free breakfast and coffee is great way to start your day. Schedule a spa day at least once so you can relax before the walk to dinner! Reception was super nice and even helped us call a taxi.

Reviewed on 21 Sept 2026

Aurum Firenze

Aurum Firenze

Historic Centre of Florence
€721
per person
25 Oct - 30 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
7.6/10 Good! (1,003 reviews)
Good location- close to all the attractions. We were there for 3 days. One day, had a downpour of rain- came back to the hotel soaking wet asked for dry towels, they declined- you only have the same towels ( which were wet from our morning shower)for your stay. Shower was a lot smaller than previous hotels that we stayed at when in Italy. Breakfast and coffee were horrible

Reviewed on 22 Sept 2026

Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

Historic Centre of Florence
€677
per person
27 Oct - 31 Oct
just found
Return direct flight included
Dublin (DUB) to Florence (FLR)
9/10 Wonderful! (1,005 reviews)
The hotel is in a centrally located area with very close proximity (walking) to major museums and shopping with no need for a car. Room was fairly clean but it seems long overdue for an update. Breakfast fee is €10 per day which is very reasonable with many choices of hot and cold items. The staff are very helpful and friendly and that is a great asset to the hotel.

Reviewed on 22 Sept 2026

Dimora Palanca Boutique & SPA

Dimora Palanca Boutique & SPA

Historic Centre of Florence
€802
per person
27 Oct - 31 Oct
just found
Return direct flight included
Dublin (DUB) to Florence (FLR)
9.2/10 Wonderful! (69 reviews)
A stunning Italian property exquisitely furnished and in the perfect location in Florence. Travelled with my daughter for her birthday trip and I doubt we could have chosen better. An extremely warm welcome, room was ready on arrival and what a room. Across the sunny courtyard in a converted stable block we found our peaceful 2 bedroom resting spot with super comfortable beds, pillows and all the amenities needed to ensure our stay was enjoyable. Every member of staff is a true credit to the Dimora. Very friendly, helpful, knowledgeable, quietly going about their duties without any inconvenience to guests and accommodating all requests without any trouble. The birthday girl was spoilt with breakfast cake, candles and a bottle of prosecco. Breakfast was excellent with plenty of choice, the bar had a wide selection of drinks to choose and we took advantage of the comfortable lounge areas to unwind after exhausting days exploring Florence. I would stay at the Dimora again without hesitation and highly recommend you do too!!

Reviewed on 20 Sept 2026

Things to do in and around Pienza

Pienza, a charming town in Tuscany, is ideal for outdoor and romantic getaways, offering a range of activities such as spa treatments and access to private country clubs. Visitors can indulge in wellness experiences and explore the picturesque surroundings, making it a perfect destination for a memorable tourist journey. With its blend of relaxation and entertainment, Pienza promises an enchanting holiday for all who venture there.

Shopping

Pienza offers a delightful shopping experience with local stores like RI Crea RE, perfect for unique souvenirs. If you're up for a drive, Valdichiana Outlet Village, located 19.3km away, features a variety of shops for fashion and lifestyle items.

Recreation

Relax at the Parco Piscine Capenti Outdoor Pool, a family-friendly aquatic centre 25.7km from Pienza, or indulge in luxury at the Chapel of Our Lady of Vitaleta, a private club just 3.2km away. Experience wellness and relaxation at the Terme di Chianciano spa, located 11.3km from Pienza.

Adventure

Experience the thrill of ziplining at Saltalbero Adventure Park, located 24.1km from Pienza, surrounded by stunning landscapes. Enjoy family fun at Tavernelle Aquatic Park, 37.0km away, with exciting water attractions. For winter sports, head to the Macinaie Ski Lift, 20.9km from Pienza, perfect for skiing adventures.

Nightlife

Pienza's nightlife offers a charming atmosphere with quaint wine bars and rustic trattorias. Visit the Enoteca di Pienza for exquisite local wines, and enjoy traditional Tuscan dishes at La Porta. For a more vibrant scene, head to Bar del Corso for cocktails and mingling with locals under the stars.

*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 the heart of Tuscany, is an idyllic destination for outdoor enthusiasts and romantics alike. Visitors can explore charming piazzas, ancient monasteries, and soothing hot springs, while indulging in the rich culture and scenic beauty the area has to offer. Key attractions include the stunning Pienza Cathedral, making it a perfect spot for those seeking a blend of cultural experiences and natural delights.

  • Pienza Cathedral: Nestled in the heart of Pienza, this stunning cathedral showcases exquisite Renaissance architecture and offers a serene atmosphere. Its intricate interior and cultural significance make it a must-visit for art and history enthusiasts.
  • Palazzo Avignonesi: Located 9.7km from Pienza, this charming piazzaSquare is rich in culture and city vibes. It serves as a lively gathering place, surrounded by beautiful buildings and offering a taste of local life, perfect for people-watching and enjoying a leisurely stroll.
  • Palazzo Borgia: Situated within Pienza, this historicBuilding is a true gem, reflecting the city's rich past. Its elegant architecture and cultural aura make it an ideal spot for those interested in exploring the history of the region.

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

  • 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.

Top hotels in Pienza

Hotel San Gregorio

Hotel San Gregorio

Via Della Madonnina 4 Pienza SI
€206
6 Oct - 7 Oct
includes taxes & fees
9.4/10 Exceptional! (157 reviews)
"Quaint but modern hotel walking distance to all - good breakfast and service in hotel restaurant. Spacious rooms with air conditioning (which gets turned off when staff cleans room - call desk to turn back on), safe, and bathroom with tub- but no shower curtain- took a while to learn how to negotiate ..."

Reviewed on 17 Sept 2026

Hotel San Gregorio
Hotel Corsignano

Hotel Corsignano

Via Della Madonnina 11 Pienza SI
€192
19 Oct - 20 Oct
includes taxes & fees
Hotel Corsignano
Agriturismo Il Macchione

Agriturismo Il Macchione

S.P. 71 Per S. Anna in Camprena Pienza SI
€212
15 Oct - 16 Oct
includes taxes & fees
Agriturismo Il Macchione
See all 6,026 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.

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.
See properties
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.
See properties

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.
See properties

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.
See properties

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.
See properties

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.
See properties

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.
See properties

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.
See properties

What to do in Pienza

Montepulciano Gran Tour

Montepulciano Gran Tour

€15
per adult
Montepulciano Gran Tour
3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch

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

€109
per adult
98% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
Chianciano Terme: Sensory Spa Admission Ticket

Chianciano Terme: Sensory Spa Admission Ticket

€59
per adult
Chianciano Terme: Sensory Spa Admission Ticket
See all activities in Pienza

Frequently asked questions

How much does a Pienza holiday package cost?
You can snap up a holiday package to this popular destination from €576 on Expedia. However, how much your holiday to Pienza costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Pienza?
You can usually find lower rates and better availability in December, January and February. Browse our cheap Pienza holiday packages and you could score some great off-season discounts.
How many days is enough for Pienza?
The ideal length for your Pienza holiday depends on what you'd like to see. Typically, a few days to a week will give you time to check out all the top attractions and explore some hidden spots along the way.
Is it worth booking a holiday package to Pienza?
Pienza has everything you need for an amazing break — walking trails, hiking and festivals are just the start. Whether you want to visit sights like Palazzo Piccolomini and Historic Centre of Pienza, or take the road less traveled, you'll have plenty to experience on your Pienza holiday.
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 holiday package as soon as possible.
Is it cheaper to book a Pienza holiday as a package?
You can enjoy significant savings on your Pienza retreat by booking a personalised holiday package. Click on the "Package" heading, then enter your destination and travel dates to see the best airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a holiday 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: The things you plan to do in Pienza and your preferred season will help you decide when to go.
  2. Budget wisely: As well as the price of your stay, you should factor in other expenses too. These include transportation, food and flights. Also, put aside a little extra for unexpected expenses that may come up during your trip to Pienza.
  3. Decide how long to go away for: Now that you know more about Pienza, you can figure out the perfect length of your break. Pull together a draft plan and give yourself enough time to cover everything you want to do.
  4. Bundle your airfare and accommodation: After you've settled on your trip dates and duration, lock in the right Pienza holiday package for you.

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.