Title: Pienza Vacation Packages & Trips 2026 from CA $1,434 | Expedia.ca [Pienza Travel Guide](https://expedia.ca/Pienza.dx6023645)[Hotels in Pienza](https://expedia.ca/Pienza-Hotels.d6023645.Travel-Guide-Hotels)[Vacation Rentals in Pienza](https://expedia.ca/Pienza-Vacation-Rentals.d6023645.Travel-Guide-VacationRentals)[Flights to Pienza](https://expedia.ca/Cheap-Flights-To-Pienza.d6023645.Travel-Guide-Flights)[Things to do in Pienza](https://expedia.ca/Things-To-Do-In-Pienza.d6023645.Travel-Guide-Activities)[Pienza Car Rentals](https://expedia.ca/Car-Rentals-In-Pienza.d6023645.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6023645/9d678ea5-9752-4000-8f7c-af307fb65e61.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Pienza Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 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 #### 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](https://www.expedia.ca/Pienza-Cathedral-Pienza.d6105122.Vacation-Attraction), [Palazzo Piccolomini](https://www.expedia.ca/Palazzo-Piccolomini-Pienza.d6105120.Vacation-Attraction) and [Chapel of our Lady of Vitaleta](https://www.expedia.ca/Chapel-Of-Our-Lady-Of-Vitaleta-San-Quirico-dOrcia.d553248623503682429.Vacation-Attraction). 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 La Scaletta Al Ponte Vecchio](https://images.trvl-media.com/lodging/2000000/1610000/1604300/1604285/9b3b942d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel La Scaletta Al Ponte Vecchio Historic Centre of Florence CA $1,434 per person Mar 23 - Mar 29 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Florence (FLR) 8.8/10 Excellent! (939 reviews) The room was fantastic! Reviewed on Jan 10, 2026 ![Villa Cora](https://images.trvl-media.com/lodging/1000000/30000/22600/22579/bc8037ee_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Villa Cora Oltrarno CA $3,314 per person Mar 21 - Mar 27 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Florence (FLR) 9.8/10 Exceptional! (467 reviews) Nice property and staff. Reviewed on Nov 13, 2025 ![Art Atelier](https://images.trvl-media.com/lodging/5000000/4060000/4053100/4053096/64645dd6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Art Atelier Historic Centre of Florence CA $1,570 per person Mar 8 - Mar 14 found 24 hours ago Roundtrip non-stop flight included Montreal (YUL) to Florence (FLR) 9.2/10 Wonderful! (1,001 reviews) The room was spacious and the terrace was very nice. The hotel is in walking distance to all the attractions and train station. Reviewed on Jan 6, 2026 ![Il Rivalta - Place of Charme](https://images.trvl-media.com/lodging/46000000/45800000/45790300/45790281/a67d0954_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Il Rivalta - Place of Charme Historic Centre of Florence CA $3,608 per person Feb 14 - Feb 20 found 22 hours ago Roundtrip non-stop flight included Hamilton (YHM) to Florence (FLR) 9.2/10 Wonderful! (420 reviews) Excellent hotel with Excellent location and Excellent staff and Excellent rooms Reviewed on Jan 1, 2026 ![The Moon Boutique Hotel & Spa](https://images.trvl-media.com/lodging/23000000/22260000/22255000/22254976/205f9600_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Moon Boutique Hotel & Spa Historic Centre of Florence CA $1,600 per person Mar 8 - Mar 14 found 24 hours ago Roundtrip non-stop flight included Montreal (YUL) to Florence (FLR) 9.6/10 Exceptional! (495 reviews) The spa was wonderful though the jacuzzi could be hotter I think! The only complaint was that the bed wasn’t very comfortable (it was pretty hard) and the pillows were rather flat. Reviewed on Jan 2, 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: ](https://www.expedia.ca/Pienza-Cathedral-Pienza.d6105122.Vacation-Attraction)** 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: ](https://www.expedia.ca/Terme-Di-Montepulciano-Spa-Montepulciano.d6169786.Vacation-Attraction)** 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: ](https://www.expedia.ca/Palazzo-Ricci-Montepulciano.d553248621532500182.Vacation-Attraction)** 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. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | ---------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------- | | January | 39.4°F (4.1°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | | February | 40.6°F (4.8°C) | Light Rain | Mostly Sunny | Average | Slightly Low | | March | 45.0°F (7.2°C) | Light Rain | Mostly Sunny | Average | Average | | April | 50.9°F (10.5°C) | Light Rain | Mostly Sunny | Slightly High | Average | | May | 57.4°F (14.1°C) | Light Rain | Mostly Sunny | Average | Average | | June | 66.7°F (19.3°C) | Light Rain | Sunny | Average | Slightly High | | July | 73.0°F (22.8°C) | No Rain | Sunny | Average | Slightly High | | August | 73.0°F (22.8°C) | No Rain | Sunny | Slightly High | Slightly High | | September | 64.8°F (18.2°C) | Light Rain | Mostly Sunny | Slightly High | Average | | October | 56.7°F (13.7°C) | Light Rain | Mostly Sunny | Average | Average | | November | 48.6°F (9.2°C) | Light Rain | Mostly Sunny | Slightly Low | Average | | December | 42.1°F (5.6°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly 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 Relais II Chiostro di Pienza](https://images.trvl-media.com/lodging/1000000/900000/893100/893017/ef61d192_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Relais II Chiostro di Pienza Corso Rossellino 26 Pienza SI 8.6/10 Excellent! (614 reviews) A little tired, extremely clean, with an amazing staff Reviewed on Jan 1, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=26%2F01%2F2026&endDate=27%2F01%2F2026&selected=893017&PinnedHotelID=893017&HadPinnedHotel=true®ionId=6023645) [](https://expedia.ca/Hotel-Search?startDate=26%2F01%2F2026&endDate=27%2F01%2F2026&selected=893017&PinnedHotelID=893017&HadPinnedHotel=true®ionId=6023645) ![Hotel San Gregorio](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/9fda43a3_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel San Gregorio Via Della Madonnina 4 Pienza SI Fully refundableReserve now, pay when you stay 9.2/10 Wonderful! (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 [Get rates](https://expedia.ca/Hotel-Search?startDate=26%2F01%2F2026&endDate=27%2F01%2F2026&selected=2692135&PinnedHotelID=2692135&HadPinnedHotel=true®ionId=6023645) [](https://expedia.ca/Hotel-Search?startDate=26%2F01%2F2026&endDate=27%2F01%2F2026&selected=2692135&PinnedHotelID=2692135&HadPinnedHotel=true®ionId=6023645) ![Hotel Corsignano](https://images.trvl-media.com/lodging/3000000/2530000/2525700/2525690/e0c5b2be_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Corsignano Via Della Madonnina 11 Pienza SI CA $293 CA $333 total Feb 7 - Feb 8 includes taxes & fees 9.4/10 Exceptional! (328 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 [](https://expedia.ca/Hotel-Search?startDate=07%2F02%2F2026&endDate=08%2F02%2F2026&selected=2525690&PinnedHotelID=2525690&HadPinnedHotel=true®ionId=6023645) [See all 5,887 properties in Pienza](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=13%2F01%2F2026&endDate=14%2F01%2F2026®ionId=6023645) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### Discover the most popular places to visit in Pienza ![Cathedral of Pienza featuring religious elements, a church or cathedral and heritage elements](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/208000/208193-Cathedral-Of-Pienza.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Pienza Cathedral Admire the arresting Renaissance façade and the interior Gothic décor of this 15th-century cathedral commissioned by Pope Pius II. [](https://expedia.ca/Pienza-Cathedral-Pienza.d6105122.Vacation-Attraction) #### Art Studio di Adelina Quadri You can spend an afternoon browsing the exhibits at Art Studio di Adelina Quadri during your travels in Monticchiello. While you're here, you can savor the wineries. [](https://expedia.ca/Art-Studio-Di-Adelina-Quadri-Pienza.d553248621562145321.Vacation-Attraction) ### What to do in Pienza ![3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch](https://mediaim.expedia.com/localexpert/47282553/e14b5a73-0ff4-428f-a567-234540a94e59.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch CA $143 per adult **100%** of travellers recommend [](https://expedia.ca/things-to-do/from-rome-bagnoregio-orvieto-day-trip-with-tuscany-wine-tasting-lunch.a47282553.activity-details) ![Seggiano: Guided Tour of the Olive Grove and Food Tasting](https://mediaim.expedia.com/localexpert/48314154/3c3e6332-4460-423d-8ee4-7953fc5d8637.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Seggiano: Guided Tour of the Olive Grove and Food Tasting CA $40 per adult [](https://expedia.ca/things-to-do/seggiano-guided-tour-of-the-olive-grove-and-food-tasting.a48314154.activity-details) ![Montalcino: Guided Winery Tour and Wine Tasting](https://mediaim.expedia.com/localexpert/44628122/e1c18867-816c-4ff5-aaae-8b2f08187f9c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Montalcino: Guided Winery Tour and Wine Tasting CA $72 per adult [](https://expedia.ca/things-to-do/montalcino-guided-winery-tour-and-wine-tasting.a44628122.activity-details) [See all activities in Pienza](https://expedia.ca/things-to-do/search?rid=6023645) ## Explore a world of travel with Expedia - 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