Villa Castrum

Tuscany, Italy

  • 10
  • 5
  • 4
  • Magnificent 5-bedroom villa
  • Part of a beautifully restored historic hamlet
  • In the heart of Chianti
  • Spacious and comfortable
  • Enchanting walled garden
  • Private pool
  • Simpson family extras available

Advance Registration... select your dates and reserve your 2023 holiday online, with a fully refundable deposit of £500.

This imposing villa stands on the hilltop site of the 1,000-year-old Castle of Cortine, deep in the heart of Tuscan Chianti. Part of the sprawling Canonica di Cortine estate, Villa Castrum is set in its own gated grounds with private gardens and secluded swimming pool reserved exclusively for villa guests. The entire region is dotted with ruined castles and fortifications that bear witness to its turbulent medieval history, but visitors today will find an eminently more civilised landscape of rolling hills, olive groves and, of course, the vineyards that produce some of Italy’s best-known wines.

With its solid stone walls and lofty beamed ceilings, Villa Castrum has been tastefully restored to create comfortable accommodation for up to 10 guests. However, the adjoining self-contained apartment, Il Palagetto, can also be booked on request to accommodate larger groups of up to 14. It creates a flexible space for two families or a multi-generational get together and meals are made easy with the option to enjoy breakfasts, light lunches and dinners in the estate dining room (payable locally with advance booking advisable).

Your hosts, Lucia and Stefano, are on hand to provide any day-to-day assistance, and can help you organise a range of holiday-enhancing experiences, from a private chef and beauty treatments to wine tastings or an unforgettable vintage Fiat 500 tour of the Chianti countryside.

The local area

For a meal with celebrity cachet, your nearest restaurant is less than 1.6km away and once hosted George Clooney. It’s easily walkable, but the road isn’t paved or lit at night, so a long lunch rather than dinner is the better bet.

Otherwise, the nearest village is San Donato in Poggio, 2.5km away, where you’ll find basic shops and a handful of small restaurants. More extensive facilities are on offer at Barberino Val d'Elsa just a 15-minute drive from the villa. This medieval gem overlooks the Elsa River valley and is typical of the many authentically unspoilt smaller towns in this area. The big names are not far away, however, with no less than seven UNESCO World Heritage Sites within convenient driving distance. Florence, Siena, San Gimignano and Greve are all under an hour’s drive, while Pisa, Lucca, Volterra and the seaside resort of Versilia can be reached in 60 to 90 minutes by car.

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  • 5-bedroom villa (sleeps 2-10)

Ground floor

  • Large sitting room with piano and fireplace
  • Dining room
  • TV room
  • Kitchen includes hob, electric oven, filter coffee machine, fridge-freezer, dishwasher
  • Double bedroom with en-suite shower room
  • Shower room
  • Separate WC

First floor

  • Master bedroom with en-suite bathroom
  • Double bedroom with en-suite shower room
  • Twin bedroom
  • Twin bedroom (can be configured into a double if required) open to small balcony with garden view
  • Bathroom

Il Palagetto

Please ring for a price if you wish to include Il Palagetto in your holiday

  • 2-bedroom apartment (sleeps 2-4)
  • Open plan dining/kitchen area; French doors open to outdoor dining area under olive trees
  • Kitchen includes hob, electric oven, filter coffee machine, fire place (decorative), fridge-freezer, dishwasher, washing machine
  • Double bedroom
  • Twin bedroom
  • Shower room
  • Separate WC


  • Complimentary WiFi
  • Satellite TV
  • Air-conditioning in all bedrooms
  • Central heating (payable locally)
  • Barbecue
  • Outdoor dining area
  • Private swimming pool 15m x 8m (depth 1.50m throughout)
  • The door adjoining the main villa and Il Palegetto can be locked when not in use.
  • In Italy, a daily tourist tax applies for the first week of your stay only, which means that an average of €1.50 per person (12+ years) may be charged. This should be paid in cash to your villa or hotel owner during your stay.
  • Due to the cooler temperatures, the swimming pool will be closed from 30 September until the end of the season
  • Security deposit (£750) required 3 weeks prior to departure.
  • Our Covid-19 pledge means your holiday is fully protected. However, there may be special conditions surrounding flexible booking at this property. For further details, please visit: /covid-pledge-flexible-booking.

Simpson family extras

  • Complimentary cot and highchair available
  • Car seats and booster seats can be provided at a supplement, subject to availability
  • To pre-book any of our family extras please call 020 8392 5747


  • All properties with WiFi are able to support basic functionality such as web browsing and checking emails. We aim to offer an uninterrupted service but sometimes due to factors beyond our control reliability can be affected.

Access times

  • Check in time – 4:00pm - 8:00pm
  • Check out time – 10:00am


  • Restaurant 20min walk
  • San Donato in Poggio 5min drive
  • Radda in Chianti 30min drive
  • Greve in Chianti 30min drive
  • San Gimignano 35min drive
  • Gaiole in Chianti 40min drive
  • Siena 50min drive
  • Florence 1hr 10min drive
  • Pisa airport 1hr 30mins drive


This property is priced on an accommodation-only basis. To view details of recommended flights please click here.

Car hire

We are happy to arrange your car hire in Italy; please click here to view options and prices. All hire cars booked with us include: 

  • Fully inclusive insurance, with zero excess*
  • Free additional driver

When you book your car with us, we'll also make sure the paperwork is done in advance, leaving you free to simply check and sign for the vehicle when you arrive. For further information regarding travel arrangements click here.

* For this particular destination, the undercarriage is not included in the cover.



Customer feedback

Nice hosts. Large, interesting villa with nice atmosphere.
Simpson Traveller – July 2019

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From the moment you arrive in Tuscany, you are invited to share in its grand passions and indulgent pleasures – world-famous wine, mouth-watering food and epic histories. Each of Tuscany’s ten provinces has its own unique personality, but wherever you stay, you’ll find yourself surrounded by a verdant patchwork of olive groves, cypress trees and vineyards. From the birthplace of the Renaissance, Florence, to the narrow streets of hilltop San Gimignano, Tuscany makes for a stunning escape. 

To complete the picture, explore our collection of handpicked villas and charming apartments.

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Read more on our Tuscany region page

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