
Villa Castello
Castiglion del Bosco · Sleeps 6

Historic Estate
Cortona
Sleeps 18 · 9 bed · 10 bath
Represented by Exclusive Tuscany
18 guests · 9 bedrooms · 10 bathrooms
Price on enquiry
A personal reply from Smaranda within 24 hours. No obligation.
Keep this house
The essence
At the foot of the Etruscan hill town of Cortona, Villa della Cappella is a 17th-century villa restored over two years into a private retreat for eighteen guests across nine bedrooms. More than 1,000 square metres of frescoed ceilings, terracotta floors and antique furniture open onto a fully fenced seven-thousand-square-metre park — lawns, centuries-old trees, potted lemons and an oleander-lined drive leading to the pool and a stone gazebo built for long, unhurried dinners.


























































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The distinction
A genuine 17th-century restoration: frescoed vaulted ceilings, painted walls and terracotta floors across more than 1,000 square metres, overseen by architects and interior designers for two full years.
A private chapel on the grounds — Villa della Cappella is licensed and set up for weddings, not just large enough to host one, with a run of five-star guest reviews naming the hosts by name.
The ground floor is one grand frescoed salon with an antique billiards table; upstairs, nine panoramic bedrooms with romantic four-poster beds and marble en-suite bathrooms.
The house
Nine bedrooms across the upper floors, each with a four-poster bed, its own character, and a marble en-suite bathroom. The ground floor is dominated by a single grand salon — vaulted, frescoed ceilings, painted walls, and an antique billiards table — built for a whole group to gather in one room rather than scatter across several. A games room adds board games and ping pong for the days when the weather keeps everyone inside.
The setting
At the foot of Cortona's walls, in the hamlet of Ossaia, with the town's cafés, boutiques and restaurants a short walk or drive away. Montepulciano is thirty-five minutes, Siena under an hour, and the hill towns of the Val d'Orcia — Pienza, Montalcino — an easy morning's drive. Villa Bramasole, the villa made famous by Under the Tuscan Sun, is nearby but is a separate, distinct property.
Where it sits
Approximate location: the nearest village, not the house itself. The exact address comes with your booking confirmation.

Living here
The completely fenced park — lawns, century-old trees, potted lemon trees and an oleander-lined drive — wraps a large pool and jetted jacuzzi, with a stone gazebo furnished for al fresco lunches and dinners a few steps away. It is a house built as much for a wedding as for a holiday: the private chapel, the grand salon and the grounds are all sized for a full celebration, and the family who run it handle vendors and logistics directly rather than through an agency.
Pricing
Villa della Cappella is available to book through us directly. Tell us your dates and party, and we’ll reply within 24 hours with the exact rate and availability, with no obligation.
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