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Villa Tregole

Castellina in Chianti - Siena and Chianti

14 7 7 Private Pool
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, side table, 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, washing machine.

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 tables, wardrobe, day bed, chair, air conditioning.

En-suite Bathroom
Shower, sink, WC, bidet.

Bedroom 4
Double bed (cannot be converted into twin beds), bedside tables, wardrobe, chair, luggage stand, round table, air conditioning.

En-suite Bathroom
Large shower, sink, WC.

Apartment 1
Ground Floor

Lounge/ Kitchen

Sofa, two armchairs, coffee table, open fireplace, chest of drawers, fully equipped kitchen, fridge/ freezer, gas hob with 4 rings, table, 4 chairs, door to terrace.

Bedroom 5
Double bed (cannot be converted into twin beds), cupboard, built-in bookshelf, chair, luggage stand, air conditioning.

En-suite Bathroom
Large shower, sink, bidet, WC.

First Floor

Small Lounge

Sofa, armchairs, 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, chair, 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.

Bathroom
Sink, WC, shower.

Bedroom 7
Double bed (cannot be converted into twin beds), bedside tables, cupboard, chair, luggage stand, air conditioning.

Bathroom
Bathtub with shower attachment, sink, WC.

Private 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: No
Furnished: Sunlounger and gazebo
Cleansed: Chlorine-free
Distance from villa: 50meters

Price & Availability

Date Ranges

7 night price

21 Mar 2026 - 23 May 2026

4,835 Euro

23 May 2026 - 4 Jul 2026

5,580 Euro

4 Jul 2026 - 5 Sept 2026

7,440 Euro

5 Sept 2026 - 19 Sept 2026

5,580 Euro

19 Sept 2026 - 7 Nov 2026

4,835 Euro

7 Nov 2026 - 12 Dec 2026

4,835 Euro

12 Dec 2026 - 2 Jan 2027

5,580 Euro

Villa Facilities

Flexible dates
Washing Machine
Air-conditioning
Internet
Terrace

Villa floor plans

Good To Know

Usage to pay on-site: Heating Villa, Air Conditioning
Tourist tax to pay on-site: 1.50 € per person, per night for the first 7 nights, some exemptions apply.
Meet and greet: Arrival time is 16:00 - 19:00. Departure time is before 10:00. 

Villa Location

Distance

Airports:

Distances and driving time

  • Airport Florence: 62km - 1h 00m
  • Airport Pisa: 108km - 1h 36m
  • Airport Perugia: 137km - 1h 40m

Towns with Amenities:

Distances and driving time

  • Castellina in Chianti: 5km - 0h 09m
  • Ambra: 8km - 0h 15m
  • Castellina Scalo: 15km - 0h 17m

Guest Reviews

Jane

July 28, 2023

Group of friends

United Kingdom

Tregole is in the most beautiful location with all of the amenities you could want. The outside area is spectacular with a wonderful feeling of calm and tranquility. The rooms are airy and bedrooms have air conditioning. We were a group of 13 celebrating my husbands birthday and it was perfect. We visited Sienna and Florence, all within an hour’s journey( Florence a little further). The pool area was brilliant!We walked to the local village through the woods and ate in the local restaurant but we loved Castellina in Chianti for eating out which is about a 5 minute drive away. We took advantage of the home made pizza night and Italian dinner in Tregole itself provided by the owners which was just brilliant along with their wine produced on their vineyard which was excellent.

To Tuscany team comments for this review:

Thank you very much for your wonderful review. We are delighted that you had a lovely time at Tregole and happy to hear that it was the perfect place to celebrate your husband’s birthday. We hope to see you in Tuscany again soon !