7 nights from
$6,102 to $9,389
Tregole, Castellina in Chianti - Siena and Chianti
The vine-clad hills of Chianti are the classic image of Tuscany and the beautiful backdrop for Villa Tregole. Here in the heart of the Classico vineyards, a working winery has been turned, in part, into a supremely comfortable property where groups of friends or extended family can gather.
You could easily immerse yourself in the rural solitude of this peaceful retreat, where the sound of the winery’s activity provides a gentle distraction and a cultural connection. You might only stray from your lounger to enjoy a tasting of the owner’s wines, or to trace the path through the woods for lunch at the restaurant in Fonterutoli. Yet there are so many nearby temptations for an outing – the Classico wineries, the historic towns of Castellina and Radda, the charming city of Siena, and some fantastic mountain biking and walking terrain.
This handsome stone property is next to the welcoming owner’s home yet completely private. It’s such a clever choice for get-togethers. Inside the main house, a spacious living room leads to a large kitchen-diner. The four bedrooms, all en-suite, are on the first floor, away from the hubbub. Two separate apartments offer a little more privacy for those who like their space. Throughout the rooms, prettily decorated in pastel shades, you’ll find the traditional features of a Tuscan country home – large fireplaces, terracotta floors, wooden beams, vaulted ceilings, shuttered windows.
All three dwellings have private entrances, yet spill out onto open and covered terraces that take full advantage of the villa’s setting on a ridge. Here you can dine on feasts of your own making – or created to order by the owners – while gazing at the rolling hills laced with olive groves and oak woods. Below is a luxurious pool with a wraparound sundeck – yet another place from which to indulge in this villa’s main pursuit, the idle contemplation of dreamy views.
Ground floor
Lounge/ Diner/ Kitchen
Two sofas, armchairs, coffee table, two wicker chairs, side table, Smart TV, dining table with 14 chairs, open fireplace, desk, Welsh dresser, fully equipped kitchen, fridge/ freezer, gas hob with 5 rings, two French doors to garden and terrace, terrace with a large tables and chairs.
Bathroom
WC, sink.
First Floor
Bedroom 1
Pair of twin beds (can be converted into a double if requested when booking), bedside table, wardrobe, chair, table, air conditioning.
En-suite Bathroom
Shower, sink, bidet, WC.
Bedroom 2
Double bed (cannot be converted into twin beds), bedside tables, corner wardrobe, table, chair, air conditioning.
En-suite Bathroom
Shower, sink, WC.
Bedroom 3
Double bed (cannot be converted into twin beds), bedside table, wardrobe, chair, round table, air conditioning.
En-suite Bathroom
Shower, sink, WC.
Bedroom 4
Double bed (cannot be converted into twin beds), bedside tables, wardrobe, sofa, chair, chest of drawers, luggage stand, air conditioning.
En-suite Bathroom
Large shower, sink, bidet, WC.
Apartment 1
Ground Floor
Lounge/ Kitchen
Sofa, two armchairs, coffee table, TV, open fireplace, chest of drawers, round table, fully equipped kitchen, fridge/ freezer, gas hob with 4 rings, table, 4 chairs, French door to terrace.
Bedroom 5
Double bed (cannot be converted into twin beds), bedside tables, cupboard, built-in bookshelf, chair, luggage stand, air conditioning.
En-suite Bathroom
Large shower, sink, bidet, WC.
First Floor
Small Lounge
Sofa, armchair, wooden chest, side table.
Bedroom 6
Pair of twin beds (can be converted into a double if requested when booking), bedside tables, wardrobe, luggage stand, air conditioning.
En-suite Bathroom
Shower, sink, bidet, WC.
Apartment 2
Ground Floor
Lounge/ Diner
2 Sofas, coffee table, TV, open fireplace, table, 3 chairs, French door to terrace, terrace with table and chairs.
Kitchen
Fully equipped kitchen, fridge/ freezer, Welsh dresser, gas hob with 4 rings.
Bedroom 7
Double bed (cannot be converted into twin beds), bedside tables, cupboard, chair, luggage stand, air conditioning.
En-suite Bathroom
Bathtub with shower attachment, sink, WC.
Pool
Length: 14 meters
Width: 7 meters
Depth: 1.20 - 2.20 meters
Entrance: Roman steps
Opening times: 15th May to end of Sept
Fenced: Yes
Furnished: Sunlounger and gazebo
Cleansed: Chlorine-free
Distance from villa: 50meters
Facilities
Villa rates
- 2023
House rules
The Security Deposit is €500 payable only in Euro cash is required on arrival. You will be reimbursed on check-out should no damage occur during your stay
Tourist tax: 1,50 € per person, per night for the first 7 nights, some exemptions apply.
Charged based on usage: Heating Villa, Air Conditioning
Arrival guide
Meet and greet
Arrival time is 16:00 - 19:00. Departure time is before 10:00.
Approach road: Unpaved, even
Parking: Private, onsite parking - 10 uncovered spaces

Let us help you with your enquiry
1-929-445-5929 Toll Free
Layout (500 sqm)
































Villa location
Guest reviews: Tregole
Edith and Sofia, our hosts, were the most remarkable mother-daughter team -- friendly, accommodating, just wonderful. The location is simply spectacular -- not only are the views amazing, but no matter how hot it is anywhere there is always a breeze. Castellina, a fantastic little town, is five minutes away; Florence and Siena are easily accessible. This might be the most beautiful part of Chianti period. Last but not least, the outdoor space is wonderful for pure relaxation -- huge pool, many places to sit and read, and views onto other wine estates that cheer the eye (even before you start drinking the local wine!). We loved it and will definitely come back!- Castellina, Radda, SIena, Florence obviously worth visiting - Antica Trattoria della Torre in Castellina, L'alberghaccio of castellina, are two local stand outs; having said that we didn't have a bad meal. - We visited the Antinori winery which was both amazing and had a fabulous restaurant; I also recommend their agriturismo for fantastic food.

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