Castellaccio 144

San Donato in Poggio, Chianti

A classic Chianti villa with pool and tennis court

A classic Chianti villa, Castellaccio is nestled in one of nature's amphitheatres, surrounded by gently rising hills of green and the occasional distant villa. Inspired perhaps by the lay of the land and certainly assisted by gifted gardeners, its owners have created a property that stretches languidly over many levels and invites free flowing movement from one to another. With accommodation in the main house and a spacious barn, this is an excellent place for a group of friends or a multi-generational family to find space for joyous gathering or tranquil retreat.

From the entrance to the fenced property, wide banks of rosemary and lavender and tall flowering shrubs draw you along the path to an umbrella-shaded panoramic terrace whose tables are a natural venue for al fresco meals. Wide staircases flanking the terrace lead up to a larger flagstone terrace between the barn and the house, the stone facade of which is softened and shaded by the wooden pergola draped with roses and white wisteria and furnished with wicker sofas.

Nice little touches

  • Tasty light fare at the restaurant at the top of the road is in walking distance
  • Great spots for meals al fresco - on the dining terrace overlooking the pool and sheltered under the pines near the BBQ
  • Beautifully landscaped gardens lend a touch of color in all seasons

Good to know

  • Mobile phone coverage is better outside from some points in the garden, hence the availability of an in-house phone for local calls.
  • The last part of the approach road is best taken in low gear, slow and steady, both heading down and back up.


As is natural in this part of the world, entry into a house through its kitchen, and Castellaccio's has long marble counters, built-in appliances, a handy breakfast table and a wood stove. Doors from the kitchen lead to an attractive dining room with a table for 10, off of which is a small office with a single bed and access to the inner courtyard.

Off the dining room, a corridor, brightened by the arched glass doors from the court, provides access to the upper floor bedrooms, a colorful tiled shower room and the large living room. With an ancient pietra serena fireplace, deep sofas covered in warm russet fabrics and painted wooden furniture, this is a room to retire to at the end of the day and relive the day's adventures.

The furnished inner courtyard, partially open to the sun but closed off by a huge wooden door, is another great place for dinner as it is steps away from the pizza oven. Also off the courtyard is the laundry and an external staircase to a loggia with bistro table and chairs which in turn accesses the upper floor bedrooms. There is a beautiful double bedroom with fireplace, which shares a large bathroom with the smaller adjoining twin/double bedroom, as well as another bathroom and a third bedroom under strong chestnut eaves, which can be a double or twin as desired. Both bathrooms have clawed tubs and roomy showers, and all bedrooms are nicely furnished with country antiques and attractive spreads.

Across the terrace from the house are arched doors to the stone barn whose wide entryway features an Arabian-style double bed behind drapes to one side and a large shower room behind an antique turquoise door to the other. A few steps lead down to an enormous sitting room with a tall stone fireplace and generous sofas that invite lounging. There is a handy kitchenette in the corner and wide French doors out to a patio whose travertine table, nearby barbecue and hammock strung in the shade of tall trees all suggest an ideal place for a summer meal.

Steps away is a gate to one of the hidden joys of the property, a long arboured walkway whose sides and hanging vines spill over with seasonal colour and perfume, and at the end of which is another surprise, a regulation tennis court. Steps from the limonaia lead down to the long pool with a furnished pergola at one end and a living area under the trees at the other.


Villa Type

  • Villas with pools
  • Private pool
  • Recommended
  • Multi-gen villa

Villa Details

  • Private pool
  • Fireplace
  • Central heating (extra)

Bedrooms and Bathrooms

  • 1 double bedroom on the 1st floor of the main house with ensuite bathroom with separate shower
  • 2 twin/double bedrooms on the 1st floor of the main house with shared bathroom with separate shower
  • 1 single bed in the ground floor study, utilized on request
  • 1 shower room on the ground floor of the main house
  • 1 double bed and shower room in the barn annex
  • Insect screens on some bedroom windows and mosquito nets
  • Portable fan in each bedroom
  • 2 hair dryers available

Kitchen equipment

  • Oven
  • Italian coffee maker
  • Dishwasher
  • Kettle
  • Toaster


  • 1 baby bed and 1 high chair available on request
  • Dvd player
  • Fireplaces
  • Wifi internet
  • Telephone for local calls
  • Iron and ironing board
  • Cd player/radio
  • Tv with satellite
  • Washing machine


  • Swimming pool (5 x 15 m; depth 1-1.5 m)
  • Barbecue
  • Pizza oven
  • Furnished gardens and terraces


  • Swimming pool with step entry set below the level of the house with living areas at opposite ends of the pool
  • Tennis court on site, with a few so-so rackets available

What's included

  • Pool towels provided
  • Mid-week cleaning
  • Final cleaning included

Extras on request

  • Arrival groceries available on request
  • Catering available on request
  • Cooking lessons available on request
  • Extra cleaning and linen change available
  • Babysitting occasionally available


Click on any photo to enter gallery

Where is Castellaccio?

Getting here

  • Florence airport: 40 mins
  • Pisa airport: 1 hr 20 mins
  • Rome airport: 3 hrs 15 mins

Around Castellaccio

In walking distance, albeit uphill, from the house there is a bar/enoteca at the crossroads of Sicelle, but when energy and an adventuring spirit draw visitors further afield, know that there is a short-cut drive to the famous Chiantigiana, the scenic road leading through the most well-known Chianti villages.

Wine tasting, lively village markets and summer concerts and exhibitions are easily within reach. And tucked away in the hills as it may seem, Castellaccio is actually not far from the highway that puts you equidistant to medieval Siena or Renaissance Florence. Step out to savour culture-rich history and still make it home for a poolside sunset and a glass of red - that is a Tuscan holiday.


  • Bar, restaurants, shopping san donato in poggio, 5km
  • Chianti villages panzano 8km,
  • Radda in chianti 20km
  • Greve in chianti 15km
  • San gimignano 32km
  • Florence 42km
  • Siena 50 km

Local Towns and Places to Visit

Click on any photo to enter gallery

From € 454 per day

How to book

Is Castellaccio perfect for you?

You can check availability and pricing here:
Check calendar
this will go to our sister site, - where you can place a hold on the dates you're interested in.

Ask us for more details - all our agents visit our villas and know the areas. You can ring us or fill in our wishlist form

Not sure?

It can often be faster to contact us to ask for advice - we visit all the houses so can give you first hand advice based on your wishlist. Once you find a villa you like we can hold dates for you for up to 48 hours while you check flights or make sure everybody is on board.

Found it? Everybody on board?

When you want to secure your booking you can login and pay the deposit (30% of total) via our secure servers or ring us directly. The balance will then be due 10 weeks before you travel. You can select the currency you want to pay in when booking - that rate is then guaranteed.

For more details see our Booking Conditions.

Any more questions?

Please ring us with any queries - there are a lot of answers in our FAQ page too. If you want to keep searching, have a look at our suggestions below!

Ask a Specialist

Dan Wrightson
UK and Europe
UK Head Office: Dan Wrightson
+44 (0)20 8444 9500
Manuela Vernaccini
Denmark and Scandinavia
Ponti & Sofia: Manuela Vernaccini
New Zealand
Eurovillas and Tours: Michelle
Tel. +64 9 302 1505
Neville and Jenny Reid
Neville and Jenny Reid
+1 416-424-2190
Julie Silberman
USA East & Florida
Julie Silberman
+1 561-312-0953
Hugh and Barbara Barton
US East
Barton & Barton: Hugh and Barbara Barton
Tel. +1 703 370 3868
All Payments are secured by
  • American Express icon
  • Visa icon
  • MasterCard icon
  • Xero icon
  • PayPal icon