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A historic town perched on a hillside with a prominent church tower, surrounded by lush greenery and rolling hills in the background.

Find 5 Star Hotels in Pienza from $123

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    Check prices for these dates, December 13 – 14, 2026

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    Our top choices for Pienza 5-star hotels

    1. Villa di Piazzano - Small Luxury Hotel of the World

    A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a stone building in the background.

    2. Precise Tale Poggio Alla Sala

    An aerial view of a large estate with multiple buildings, a swimming pool, and well-maintained gardens.

    3. Fonteverde Thermal Spa Resort Tuscany

    A woman sitting by a pool with a scenic view of hills and trees.

    4. Castiglion del Bosco, A Rosewood Hotel

    A villa with a swimming pool, surrounded by trees and hills.

    5. Castello di Velona Resort Thermal SPA & Winery

    A stone building with a pool overlooking a mountainous landscape.

    6. Hotel Certosa Di Maggiano

    A hotel room with a large bed, a vanity with a mirror, and a green archway.

    7. La Posta Hotel & Thermal Spa

    A pool with a tree in the center, surrounded by a deck and a view of hills in the background.

    8. Monastero di Cortona Hotel & Spa

    A terrace with sun loungers, stone walls, and potted plants.

    9. Il Falconiere - Relais e Chateaux

    A gazebo with a glass enclosure, surrounded by potted plants and wicker furniture, overlooking a scenic landscape.

    10. Castel Monastero - The Leading Hotels of the World

    A pool area with lounge chairs and umbrellas, surrounded by greenery and a historic building in the background.

    11. Borgo Sant'Ambrogio Resort

    A large estate with multiple buildings, a swimming pool, and expansive green fields.

    12. Mercure Petriolo Siena Terme Spa Hotel

    A pool with a modern water feature and a stone structure.

    13. Castello Banfi - Il Borgo - Relais et Chateaux

    A stone wall with a view of rolling hills and mountains.

    14. ADLER Thermae

    A couple in a hot spring with a large rock formation in the background.

    15. Relais La Corte dei Papi

    A grand banquet hall with ornate ceiling, long tables set for a formal event, and elaborate floral centerpieces.

    16. Podere Cavalbianco

    A stone villa with a swimming pool, outdoor seating, and a scenic sunset view.

    17. Castel Porrona Relais & Spa

    Spa treatment

    18. Agriturismo San Fabiano

    A dining area with a long table set for breakfast, featuring bread, pastries, and fruit.

    Top Pienza Hotel Reviews

    Borgo Sant'Ambrogio Resort

    A large estate with multiple buildings, a swimming pool, and expansive green fields.

    Capanna Suites

    A poolside area with lounge chairs, a table with drinks, and a view of hills.

    Lupaia

    A large estate with multiple buildings, a well-maintained garden, and a vineyard in the background.

    Locanda In Tuscany

    A rustic interior with exposed brick walls, a stone archway, and wooden furniture.

    La Posta Hotel & Thermal Spa

    A pool with a tree in the center, surrounded by a deck and a view of hills in the background.

    Relais Val d'Orcia

    Terrace/patio

    Terra Antica Resort

    Terrace/patio

    Relais Villa Grazianella - UNA Esperienze

    A spacious living room with a leather sofa, a wooden coffee table, and a view through large arched windows.

    La Locanda di San Francesco

    A crowded restaurant with brick walls and multiple tables and chairs.

    Agriturismo Merigge Wellness & Spa

    A dining table with two wine glasses, a candle, and a bottle of champagne, overlooking a swimming pool and a tree.

    Casa Franci Montalcino

    A hot tub with a view of a historic building and mountains.

    Castiglion del Bosco, A Rosewood Hotel

    A villa with a swimming pool, surrounded by trees and hills.

    Hotel Certosa Di Maggiano

    A hotel room with a large bed, a vanity with a mirror, and a green archway.

    Monastero di Cortona Hotel & Spa

    A terrace with sun loungers, stone walls, and potted plants.

    Podere San Giuseppe

    A pool surrounded by lavender and yellow flowers, with a stone wall and a building in the background.

    I Borghi dell'Eremo

    A stone building with a wooden door and a stone archway, surrounded by a garden with flowers and shrubs.

    Palazzo Pio III

    A wooden door with a metal handle, set in a stone wall with decorative carvings.

    Find out more about Pienza

    Why not request the best during your jaunt to Pienza? After all, you love the finer things in life, both at home and when you book a getaway. You'll join the multitudes of vacationers who have made Pienza so popular in the last year. There's no reason to delay a getaway to Pienza any longer. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. Our 5-star hotels in Pienza are the perfect places to relax in during your next escape. Don't wait any longer!

    Get a Great Deal on 5-Star Hotels in Pienza

    You'll have a fantastic time at one of these 5-star hotels. Excellent service, delicious meals, and attentive guest service are all at your fingertips. You're sure to find exactly the accommodation you need. You can also look forward to an outstanding experience and fantastic customer care, so get ready for a wonderful adventure. How do you want to relax? A full-body massage to help your cares fall away? A concierge to help you suggest the next attraction to visit? High thread-count sheets, lip-smacking main courses, and even a hot tub in the bathroom...these hotels will leave you amazed. Don't want to take our word for it? Explore our listings and pick the perfect accommodation for your needs.

    You won't sleep and order room service the entire time, though. Don't worry. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what's on your agenda, the 5-star hotels in Pienza are waiting for you to relax after a busy day.

    Your Getaway Starts Today

    The results are in, and Pienza 5-star hotels are the place to be when you book your next vacation. If you've been dreaming about a vacation set here, then go ahead and book it. Expedia can help you land a great deal on accommodation. It's time to indulge yourself. Opt for one of Expedia's Pienza 5-star hotels today and decompress in complete comfort tomorrow.

    Frequently Asked Questions

    What are the best 5-star hotels in Pienza?

    Offering superior amenities and services, Expedia travelers rate ADLER Spa Resort Thermae as one of the most popular 5-star hotels in Pienza. You'll be in the lap of luxury from the second you step foot into the lobby.

    How much does it cost to stay in a 5-star hotel in Pienza?

    The amount you pay for a 5-star hotel in Pienza depends on factors like when you want to go and the length of your trip. Our insider tip for bagging an awesome deal? Use our pricing filters to check out all of the available options for your selected dates.

    What makes a hotel 5 stars in Pienza?

    From fine dining venues and 24/7 fitness centers to swimming pools and luxury bedding, the 5-star experience in Pienza is all about luxury and relaxation. But it takes more than just upscale conveniences to earn a 5-star rating. Stays must also offer exceptional services like in-room massage treatments, on-site laundry and room service any time day or night.

    Are there any 5-star all-inclusive resorts in Pienza?

    Find an upscale stay that includes your lodging, meals, bar and entertainment in Pienza with the help of our filters. Search for hotels rated 5 stars and click on the "All inclusive" filter. Double-check what's included in the upfront price. This way, you're ready to take advantage of the many perks on offer from the moment you arrive.

    What are the top 5-star spa hotels in Pienza?

    ADLER Spa Resort Thermae combines upscale accommodations with relaxing wellness programs and experiences. Select from a menu of facials, massages and more at this leading 5-star spa escape in Pienza.

    Are there any 5-star vacation rentals in Pienza?

    You won't find any 5-star vacation rentals in Pienza on our site, but there are a range of other top-rated properties worth looking into. Scan through our vacation rentals in Pienza to book the best place for your getaway.

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