Save up to £750 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
Packages with flights are ATOL protected
Discover the most popular places to visit in Val d'Orcia
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.
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.
This medieval estate blends Tuscan tradition with world-renowned winemaking excellence. Sample award-winning Brunello di Montalcino while overlooking rolling vineyards from the restored 18th-century village.
Birthplace of Italy's prestigious Brunello di Montalcino wine, Tenuta Greppo has defined excellence since 1888. Tour the historic cellars and vineyards where the Biondi-Santi family's winemaking traditions thrive.
This pentagonal medieval stronghold was the final bastion of Siena's resistance against Medici conquest. Climb its historic ramparts for panoramic Tuscan views before sampling Brunello wines at the fortress enoteca.
This historic estate, a founding consortium member, produces Italy's finest Brunello di Montalcino wines. Tour the vineyard and cellars before savouring wine pairings with local cheeses amid the Tuscan countryside.
This medieval Romanesque abbey offers a serene glimpse into monastic life amid Tuscan olive groves. Explore the intricate stone carvings and listen for occasional Gregorian chants echoing through its ancient walls.
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.
"Il nostro soggiorno è stato bellissimo. Il casale è splendido, si respira un'atmosfera d'altri tempi; la nostra camera matrimoniale era ampia e pulitissima.
Anche a Novembre, la vista della campagna della Val d'Orcia che si aveva dalla camera è indimenticabile. Abbiamo fatto bene a fidarci delle foto e delle descrizioni della struttura.
Grazie per la vostra calorosa accoglienza."
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.
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.
How can I book the best ski holiday to Val d'Orcia in 2026/2027?
Search through alpine adventures on Expedia to plan your perfect snowy ski holiday in Val d'Orcia. Just choose your dates and see what’s available. You might prefer a hotel with a heated outdoor pool, or a private chalet for après ski parties; either way, use the property filters to your ideal match. If ski-in-ski-out is important, use the map view to find those idyllic slopeside properties.
How can I find cheap Val d'Orcia ski holidays?
Boot hire, lift passes, lessons: ski holidays can get pricey, quickly. To make your ski trip more affordable, book Val d'Orcia accommodation a little further from the lifts and go self-catering to cut back on eating out. Sort your search results by price to find options from . Prices and availability are subject to change. Additional terms may apply.
Can I book last-minute ski holidays to Val d'Orcia?
Use our handy last-minute deals page to look for ski holidays to Val d'Orcia at a steal. If your dates are fixed, simply input the details and see what specials are available.
What should I consider when booking family ski holidays in Val d'Orcia?
Val d'Orcia is well set up for kids. For the teeniest ski-woks, day care in the snow is a blast. As they get older, they love whizzing around on the hill in ski school. Choose a hotel near the lifts and nursery slopes to save a whole lot of ski-carrying hassle in the mornings. With all that extra time and energy, you can take your sweet time to find a family-favourite bolthole on the mountain for hot chocolate with marshmallows ski breaks.
Can I book all-inclusive ski holidays to Val d'Orcia?
All-inclusive ski holidays are fairly rare, but you can use our filter to see if there are any available in Val d'Orcia. If not, consider booking your flights and accommodation together to save money that way instead.
When's the best time of year to plan a ski trip to Val d'Orcia?
Ski season in Val d'Orcia generally starts around December and slopes off around April. Keep an eye on the snow forecasts though, as you can often find some brilliant deals at the start or end of the season, when it’s also much quieter.
How can I find the best deals on Val d'Orcia ski holiday packages?
If you can be flexible with your ski holiday dates, avoid school holidays and instead buckle up your boots at the start or end of season. Sort your search results by price and look out for self-catered accommodation to save on notoriously expensive ski-resort drinking and dining.
Can I book a Val d'Orcia ski trip with free cancellation and/or flexible dates?
If you’re not 100% sure on plans or just want peace of mind, choose a ski holiday with free cancellation. You can use our free cancellation filter to find properties in Val d'Orcia that offer it.
Why should I book a ski holiday package in Val d'Orcia with Expedia?
Schuss your way to the slopes with Expedia’s smooth booking process. From flights to hotels and even car hire, you’ll find everything you need to plan the ultimate winter wonderland ski holiday.