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Lupaia

Tuscany, Italy • Siena • SPLURGE

avg. $603 / night

Includes $32 / night in cash back

Cash back is redeemable via Virtual Visa, Venmo, or bank transfer starting 24-48 hours after check-out

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Cash back

5% cash back on all completed stays (redeemable via Virtual Visa, Venmo, or bank transfer starting 24-48 hours after check-out)

Credit card points

Credit and debit card charges are processed directly by the hotel (i.e. not PressBeyond), meaning that any travel-specific credit card points or incentives that you normally get as a cardholder for direct hotel bookings are preserved

Hotel loyalty points

Points accrual and status eligibility with major hotel loyalty programs: Marriott Bonvoy, Hilton Honors, World of Hyatt, and others

Free breakfast

Breakfast-included rate options available

Room upgrades

Complimentary room upgrades (subject to property availability)

Extend your stay

Early check-in and late check-out (subject to property availability)

Part of Small Luxury Hotels

Location

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PB hotel design editorial

Perched on a hillside between Montepulciano and Torrita di Siena, a cluster of medieval stone farm buildings that had stood largely untouched for centuries was converted into Lupaia, a ten-room relais that treats its age not as a problem to be solved but as the entire point. The exterior stonework — rough-coursed tufa and brick, terracotta roof tiles, a wrought-iron pergola threaded with climbing vines — was left to carry its centuries of weather and repair, lit at dusk with ground-level uplights that turn the facade the color of warm embers. The pool terrace, edged in pale travertine, sits at the property's edge where the land drops away into rolling pasture and cypress-lined ridgelines, the geometry of the water the only thing about the composition that feels deliberately designed. Inside, each room arrives at a slightly different character while sharing the same vocabulary: whitewashed timber beam ceilings, antique gilt mirrors, floors alternating between aged terracotta tile and bleached wide-plank oak. One room pairs a tartan-upholstered headboard with blue-lacquered bedside lamps and a partially open bathroom dressed in navy-and-white chequerboard tile; another layers floral cushions and striped linen curtains beneath vaulted plaster ceilings. The restaurant, framed by a full brick arch and gathered around a massive stone fireplace with a rough-hewn timber lintel, hangs oil portraits alongside gilded mirrors and sets its tables on worn oak boards over a crimson rug — the atmosphere closer to a Sienese family home than a country hotel.

Travel notes

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About

Overlooking the rolling hills of Tuscany, set between Montepulciano and Pienza, Lupaia is an ancient farm estate dating back to 1622. Today, operating as a boutique hotel, it features a unique combination of nature and history, blended in total harmony. Set on a small hilltop, all rooms enjoy enchanting views over the surrounding hills and medieval villages. Each accommodation has an independent entrance and either a private terrace or garden, featuring all modern comforts, while being unique in style, decoration and details. Facilities include a restaurant, outdoor swimming pool, gym and a reading room. Various exclusive activities, like cooking classes and the Sunset Negroni experience, are available to ensure a truly memorable stay.

Amenities

Pool

Free Parking

Pets Allowed

Room service

Breakfast Included

Internet

Suites

Free Internet

Restaurant

Bar/Lounge

Lupaia Reviews

442 reviews

"This beautiful property is nestled in the hills outside Montepulciano. It is quiet, secluded and perfect for soul rejuvenation. The grounds are filled with gorgeous trees, plants, flowers and gardens that supply the chefs with fantastic produce. On the grounds there are many little sitting areas to choose from for peaceful solitude or to enjoy a cocktail. Your garden suite “Orto” was not only spacious, it was like a comfortable hug! It had its own outdoor chairs for relaxing and an umbrella table and chairs. The service was impeccable!!! Everyone…from reception to servers to housekeeping to restaurant to groundskeepers were delightful. I’ve never found better in my extended travels. Take time for one of their cooking classes! You won’t be disappointed…Chef Marco was amazingly fun to spend the afternoon with in the kitchen. This place has nailed all the finest and tiniest of details you could possibly imagine. You won’t be disappointed."

A Tripadvisor traveler review

Apr 16, 2026

"​Lupaia is nothing short of extraordinary. A serene sanctuary set amid the rolling hills of Tuscany, reached by a gravel road that instantly signals your arrival somewhere truly special. From the moment we made our reservation to our final farewell, every aspect of our stay felt seamless and personal. Traveling with family, we stayed in both a junior suite and a garden room, each beautifully appointed and thoughtfully designed to reflect the rustic elegance of the property. What truly sets Lupaia apart is its impeccable service. Every staff member greeted us with genuine warmth, creating the sense that we were not just guests, but welcomed friends. The thoughtful use of WhatsApp communication during our stay was a standout touch​,​ effortlessly connecting us with the team whether we were on the property or exploring nearby towns, always ready with recommendations or assistance. Every detail at Lupaia feels intentionally curated to elevate the experience, from the tranquil surroundings to the refined yet relaxed atmosphere. The restaurant is equally remarkable. Each evening’s tasting menu showcases fresh, local ingredients in inventive and ever-changing ways, making every dinner ​​distinctive. The à la carte lunch menu was a wonderful option, especially as we were traveling with a child who preferred something more flexible. The wine pairings were exceptional, and the bar program deserves special praise, particularly the Negronis, which were the best we’ve ever had. Lupaia is more than a luxury hotel; it is an experience defined by beauty, thoughtfulness, and a rare sense of genuine hospitality."

A Tripadvisor traveler review

Apr 10, 2026

"A Tuscan Gem. Never tire of this place - It’s beauty, comfort and hospitality. Can’t wait to be back ✨"

A Tripadvisor traveler review

Mar 21, 2026

"Absolutely spectacular from every perspective. This place is simply magic. I spend a lot of time researching and seeking out great hotels. Travel is very important to us, and equally as important is to stay in really great places. We were told about Lupaia by travel guide, Antonella Piredda (who is fabulous) and was this ever a great recommendation. The room (Nido Junior Suite) was a dream. Beautiful and comfortable and spacious. The breakfast was outstanding. The staff were friendly and SO attentive. Just go. It’s definitely a splurge, but you will absolutely not regret it."

A Tripadvisor traveler review

Dec 13, 2025

"Amazing experience across the board. Property and staff were exceptional. Everything from the scenery, location and food exceeded our expectations. We will be back."

A Tripadvisor traveler review

Nov 18, 2025

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