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.
Hotel degli Orafi

Hotel degli Orafi

Historic Centre of Florence
CA $1,900
per person
Nov 9 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.6/10 Exceptional! (1,001 reviews)
The property was beautiful, however, the toilet in my room was it functioning properly and it flooded my bathroom two nights in a row. The first night, the staff fixed it. The second night, staff simply laid towels on the floor and said someone would fix it in the morning. I had to walk on soaking wet towels to use the bathroom during the night. No offer of a reduced rate was offered. It was very frustrating!

Reviewed on Oct 4, 2026

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

Historic Centre of Florence
CA $2,001
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9.6/10 Exceptional! (600 reviews)
Extremely clean, breakfast service was awesome. Absolutely beautiful room . Shower with steam and jacuzzi settings was wonderful.

Reviewed on Oct 2, 2026

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

Cortona Old Town
CA $2,729
per person
Dec 27 - Jan 2
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
10/10 Exceptional! (337 reviews)
5 star treatment, indoor pool is a charge to use and parking is rough. Overall excellent experience. Staff is great.

Reviewed on Oct 4, 2026

Glance Hotel In Florence

Glance Hotel In Florence

Historic Centre of Florence
CA $2,347
per person
Dec 27 - Jan 2
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.4/10 Exceptional! (1,001 reviews)
Florence is a walkable city for most (uneven surfaces) making this a great location. It’s a 7 - 10 minute walk (depending on luggage) from the train station. Great rooftop pool with great views and service. The Club sandwich is among the best we have ever had. Sunset in the pool was amazing too. Breakfast was exceptional with great selection and great coffee !

Reviewed on Sep 28, 2026

Bernini Palace

Bernini Palace

Historic Centre of Florence
CA $2,405
per person
Nov 28 - Dec 4
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Florence (FLR)
9.8/10 Exceptional! (1,006 reviews)
We loved everything about this hotel. They had world class service from morning to night. We had a wonderful introduction to the hotel and a personal escort to our room. The breakfast was lovely, with a nice selection of premium products, and a beautiful dining room with china. We highly recommend Hotel Bernini, it was the perfect hotel in a perfect location.

Reviewed on Oct 3, 2026

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.

Ready to book your vacation to Pienza?

Choose your dates

Pienza Hotel Deals

Hotel Corsignano

Hotel Corsignano

Via Della Madonnina 11 Pienza SI
CA $206
CA $236 total
Nov 4 - Nov 5
includes taxes & fees
9.4/10 Exceptional! (386 reviews)
"Everything was perfect the staff the hotel."

Reviewed on Sep 24, 2026

Hotel Corsignano
Hotel San Gregorio

Hotel San Gregorio

Via Della Madonnina 4 Pienza SI
Fully refundableReserve now, pay when you stay
CA $204
CA $234 total
Oct 28 - Oct 29
includes taxes & fees
9.4/10 Exceptional! (158 reviews)
"All good"

Reviewed on Sep 30, 2026

Hotel San Gregorio
Agriturismo Il Macchione

Agriturismo Il Macchione

S.P. 71 Per S. Anna in Camprena Pienza SI
CA $242
CA $273 total
Nov 4 - Nov 5
includes taxes & fees
9.6/10 Exceptional! (76 reviews)
"멋진 곳에 자리잡은 이 농가주택은 환상적인 경험을 하게 해줬습니다. 멋진 위치와 환상적인 아침식사 멋진 스태프들. 벌써 다시 가고싶습니다. 강력히 추천합니다"

Reviewed on Oct 3, 2026

Agriturismo Il Macchione
See all 6,025 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)
Admire the arresting Renaissance façade and the interior Gothic décor of this 15th-century cathedral commissioned by Pope Pius II.
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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)
Explore the great outdoors at Historic Centre of Pienza, a lovely green space in Pienza. Discover the countryside and churches in this quaint area.
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Palazzo Piccolomini

9.4/10 (199 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.
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Monastery of Sant'Anna in Camprena

After visiting Monastery of Sant'Anna in Camprena, make a plan to see the other sights and activities in Pienza. Discover the countryside and churches in this quaint area.
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Piazza Pio II

9.2/10 (44 reviews)
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.
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Pieve di Corsignano

9.0/10 (17 reviews)
You can find out about the history of Pienza with a trip to Pieve di Corsignano. While you're here, you can savor the wineries.
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Palazzo Vescovile

9.0/10 (12 reviews)
You can find out about the history of Pienza with a trip to Palazzo Vescovile. While you're here, you can savor the wineries.
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Palazzo Borgia

8.8/10 (21 reviews)
You can study the exhibits at Palazzo Borgia, a museum with a storied past, during your trip to Pienza. While you're here, you can savor the wineries.
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What to do in Pienza

Montepulciano Wine Tasting in the Tuscan Countryside

Montepulciano Wine Tasting in the Tuscan Countryside

CA $40
per adult
Montepulciano Wine Tasting in the Tuscan Countryside
3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch

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

CA $175
per adult
98% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
Montalcino: Guided Winery Tour and Wine Tasting

Montalcino: Guided Winery Tour and Wine Tasting

CA $72
per adult
Montalcino: Guided Winery Tour and Wine Tasting
See all activities in Pienza

Frequently asked questions

How much does a Pienza vacation package cost?
You'll find cheap prices from CA $1,900 on Expedia for your Pienza escape. However, a range of factors like the length of stay, hotel choice and season will determine how much your vacation to Pienza costs.
What are the cheapest months to go to Pienza?
December, January and February are great times to look for cheap Pienza vacation packages. Choosing to travel in quieter months means you can usually find lower prices on flights and hotels.
How many days is enough for Pienza?
The ideal length for your Pienza vacation depends on what you'd like to do and see. Usually, a handful of days to a week will give you enough time to tick off all the main sights and explore some hidden treasures along the way.
Is it worth booking a vacation package to Pienza?
Well known for its walking trails, hiking and festivals, a Pienza vacation is a hit with all types of travellers. Be sure to check out top sights like Palazzo Piccolomini and Historic Centre of Pienza, and consider renting some wheels for day trips to explore even more.
How to find the best Pienza package deals?
Use Expedia's filters to help you find some unbeatable Pienza package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or search for Pienza package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Pienza vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking flights and hotels separately. Better still, you can personalize your Pienza trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Pienza?
Score incredible bargains by booking your flights early with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for an impromptu Pienza escape.
How to plan a trip to Pienza?
  1. Pick your travel dates: What you'd like to do in Pienza and your favourite season can help you decide when to travel.
  2. Work out your budget: Ensure you have enough money to pay for everything from transportation and dining out to flights and activities. Your accommodations will probably be the biggest expense during your trip to Pienza.
  3. Decide how long to go for: Now that you're more familiar with Pienza, you can work out the perfect length of your vacation. Pull together a draft itinerary and allocate enough time to cover everything you want to do.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to find a Pienza vacation package that brings all your bookings together.

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.