1/5

Each hotel image sequence, including the selection and arrangement of its images, © 2026 PressBeyond. All rights reserved

PressBeyond Logo

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

Exclusive PressBeyond Benefits

Get to where you see yourself

Ultra-clean, global, hand-picked hotel curation & imagery designed to help you visualize enticing environments and the elevated social experiences they create

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

Loading map...

At a glance

A ten-room relais in converted medieval farm buildings with original stonework, whitewashed interiors, and a fireplace restaurant.

Best for: Travelers who read buildings and rural Tuscany seekers

Highlights:

  • Medieval farm buildings converted with original tufa stonework intact
  • Ten rooms with whitewashed beams, antique mirrors, aged terracotta floors
  • Restaurant in brick-arched room with stone fireplace and oil portraits
Rustic-refinedunhurried

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

No travel notes provided yet.

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

448 reviews

"We had an incredible stay at Lupaia. The service was above and beyond, our room was beautiful and comfortable, the food was so fresh and delicious, and so much more. This stay exceeded our expectations and I would definitely recommend anyone looking in this area to stay at Lupaia."

A Tripadvisor traveler review

May 23, 2026

"An unforgettable stay from start to finish. The atmosphere, the service, and every little detail made the experience feel truly special. The staff were incredibly kind and welcoming, and the accommodation was beyond amazing. Thank you for making our stay so memorable — we can’t wait to come back!"

A Tripadvisor traveler review

May 18, 2026

"There are hotels. There are boutique hotels. There are 5-star hotels. Then there's Lupaia. I wish I could write down all the small experiences and moments that made this the most special place we've ever stayed - - but then it wouldn't be special for you. We stayed 3 nights for our 10-year anniversary and spent copious amounts of time researching if we wanted something sprawling and estate-like like Castelfalfi or something trendier like Monteverde, but we landed on Lupaia because of the intimacy and beauty. I had extremely high expectations due to the reviews, the photos, the marketing and obviously the price; it was worth every cent and surpassed my expectations, which is not easy (ask my husband). Somehow it manages to feel like your own, private multi-million dollar Tuscan vacation home while also surpassing every need before you even ask with the most exceptional service. How an experience can be so warm, understated and natural while also going above and beyond in every moment is a formula that not many can cultivate. Thank you to the team and owners and staff on your approach to hospitality. We will never forget it."

A Tripadvisor traveler review

May 07, 2026

"Magical place! Located in the hills down a very long gravel road in one of the best parts of Tuscany. Great base for day trips. Breathtaking views and attentive, warm service. They use Whatsup to communicate with you, and are always super responsive. Our room was comfortable, spacious, and clean. Great bathroom, with ample storage and counter space. This place is exceptional!"

A Tripadvisor traveler review

May 03, 2026

"Lupaia is an amazing hotel! Very beautyful, very pieceful, very private. The pool area was really nice. The staff is bespoke in every aspect! The restaruant and the food are gorgeous! Our stay was fabolus and we are defenately coming back."

A Tripadvisor traveler review

May 01, 2026

Guest photos

Guest photo
Guest photo
Guest photo
Guest photo
Guest photo

+76

Reviews and certain descriptive content powered by

Policies