Tuscany, Italy

Villa La Cipresseta

Low season per night from$2,343


Country with crystals


Grape expectations





Set on a hill in Italy’s wine-producing region of Chianti, luxury five-bedroom residence ​Villa La Cipresseta​ breathes fresh life into a former Tuscan farmhouse. The building retains its original Mediaeval stone walls, but within, the dark ages are well and truly gone thanks to a few glamorous crystal chandeliers in the rustic-chic rooms. Inside, the interiors have been lovingly restored to reflect the original Tuscan architecture – expect terracotta tiles and beamed ceilings. Enjoy barbecues on the terrace, lazy afternoons by the heated pool and restful nights in opulent antique bed heads – but don’t miss the chance to raise a glass to Chianti’s vineyards. 

Smith Extra

Get this when you book through us:

A set of Aesop bath products

First Glance

  • This traditional Tuscan farmhouse turned luxury five-bedroom villa retains atmospheric traces of former life; exposed stone walls, terracotta-tiled floors and beamed ceilings, plus one-off antiques and elegant furnishings.
  • The upstairs living room is divided in two, so guests can watch TV and movies, without disturbing others in the quieter reading and relaxing area.
  • Enjoy family meals in the fully-equipped kitchen, or dine in the elegant upstairs dining room.

Villa highlights

  • Rustic-chic Tuscan farmhouse
  • Secluded vine-draped terrace
  • Private heated pool

Sleeping arrangements

  • One of the five bedrooms has a king-size bed and the other four can be set up either with a queen-size bed or twins.
  • Each bedroom has access to a private bathroom with a shower (four of these are ensuite bathrooms).
  • Three of the bedrooms on the lower level have direct access to the gardens and one of the upper-floor rooms has a private terrace overlooking the garden and surrounding countryside.

Key kit

  • Free WiFi
  • TV
  • DVD player
  • Air-conditioning
  • SONOS music system
  • Charcoal barbecue
  • Gym
  • Boules
  • Table tennis
  • Daily housekeeping service
  • Laundry room
  • Safe


  • Paved with local pietra serena stones, the outdoor pool is set on the terrace, surrounded by 10 cushioned sunloungers, umbrellas, a pergola and some naturally shaded areas.
  • Cypress trees, vines and flowers encircle the space, making for a relaxing place to sit.
  • The pool can be heated, on request, for €60 a day.


  • Blooming flowers and verdant foliage are dotted around the secluded terrace and privacy is ensured by the twisting Cypress trees, a quintessential Tuscan staple.
  • There’s parking for four cars.


  • The hilltop town of Castellina in Chianti is less than a 10-minute drive away.
  • Florence, Siena and Pisa airports are all just over an hour away. Our Smith24 team are on hand round-the-clock to book your flights.

The Guestbook

Whenever you book a stay at a Smith hotel or villa, we’ll invite you to review it when you get back. Read what other Smith members had to say in Villa La Cipresseta’s Guestbook below.
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