1/5

Castel Monastero

Tuscany, Italy • Siena • SPLURGE

avg. $498 / night

Includes $26 / night in cash back

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

LHW Leaders Club property

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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 Leading Hotels of the World

Location

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PB hotel design editorial

A medieval hamlet in the Chianti Senese, its stone tower and cluster of farm buildings dating to the eleventh century, was transformed into Castel Monastero over a multi-year restoration that preserved the settlement's agricultural character while threading in the infrastructure of a forty-room luxury hotel. The conversion retained the original pietra serena masonry and terracotta roof tiles, and the ensemble — main manor, chapel, outbuildings, and terraced grounds — still carries the silhouette of a working podere rather than a destination resort. A contemporary pavilion housing the pool deck and restaurant loggia sits lower on the hillside, its clean concrete columns in deliberate contrast to the rougher stonework above. Inside, the interiors draw on a vocabulary of aged materials layered with restraint: exposed chestnut beam ceilings, terracotta brick floors worn smooth by centuries of use, dark-stained wood headboards set against limewashed plaster walls. Guest rooms mix antique carved writing tables and button-tufted leather Chesterfield sofas with angular Artemide task lamps, the combination avoiding the dressed-up-farmhouse trap that many Tuscan conversions fall into. The wine cellar restaurant, set within a barrel-vaulted brick undercroft lit almost entirely by candlelight and wrought-iron lanterns, is among the most atmospheric dining rooms in the region — a space where the architecture does most of the work and the decoration wisely steps aside.

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About

While painters are born, travellers are made and no land has aroused the curiosity, the enthusiasm and the culture of entire generations more than Tuscany. Certainly, not all of them have had the luck to begin their journey in the enchantment of Castel Monastero. In fact a few kilometres from our village, along roads of pure delight, can be found masterpieces of art and of the highest culinary tradition.Every day, a discovery. Every day a different itinerary passing through unspoiled scenery. Every day, on your return, a massage and a candle-lit dinner. And together, over a romantic meal for two or with your friends, you will recall the frescoes of Piero della Francesca and the perfect walls of Monteriggioni, the Renaissance utopia of Pienza and the gastronomic glory of Castellina in Chianti. And again, to surprise you, there’ll be a sunset over Pitigliano and a stroll around the Etruscan necropolises of Sovana.

Amenities

Pool

Internet

Free Internet

Free Parking

Wifi

Free Wifi

Fitness center

Room service

Suites

Restaurant

Castel Monastero Reviews

821 reviews

"The staff is amazing and very attentive they speak 5 languages and always have a smile.reception was easy to reach and everything is very convenient- the spa and restaurants are all walkable"

A Tripadvisor traveler review

Dec 29, 2025

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