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Tregole, Castellina in Chianti - Siena and Chianti

7 bedrooms 7 bathrooms 14 guests Private Pool 5 - Superb - Superb 5

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


Facilities

Washing Machine
Air-conditioning
Internet
Terrace
Garden
Barbecue
Lounge
Fire place
TV
Kitchen
Oven
Filter coffee maker
Stove top
Microwave
Dishwasher
Espresso maker
Dishes/Utensils
Ensuite bathrooms
Hairdryer
Fridge/ Freezer
Infant bed/chair
Bed linen and towels
Pool towels
Fenced property
No pets
No smoking

Villa rates

  • 2024
  • 2025
Date range
7 night price
23 Mar - 25 May 2024
$6,527
25 May - 06 Jul 2024
$7,533
06 Jul - 07 Sep 2024
$10,044
07 Sep - 21 Sep 2024
$7,533
21 Sep - 09 Nov 2024
$6,527
09 Nov - 14 Dec 2024
$6,527
14 Dec - 28 Dec 2024
$7,533
Date range
7 night price
28 Dec - 04 Jan 2025
$7,533
04 Jan - 22 Mar 2025
$6,527
22 Mar - 24 May 2025
$6,527
24 May - 05 Jul 2025
$7,533
05 Jul - 06 Sep 2025
$10,044
06 Sep - 20 Sep 2025
$7,533
20 Sep - 08 Nov 2025
$6,527
08 Nov - 13 Dec 2025
$6,527
13 Dec - 03 Jan 2026
$7,533

House rules

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


Layout (500 sqm)

Ground floor
Lounge
Kitchen
Bathroom
Terrace
Dining Room
Annex ground floor
Lounge
Kitchen
Bathroom
Bedroom
Terrace
Annex 2 ground floor
Lounge
Kitchen
Bathroom
Bedroom
Terrace
WC
Closed - no entry
Annex first floor
Lounge
Bathroom
Bedroom
First floor
Bathroom
Bathroom
Bathroom
Bathroom
Bedroom
Bedroom
Bedroom
Bedroom

Villa location

The nearest airports:
  • Airport Florence: 62km - 1h 00m
  • Airport Pisa: 108km - 1h 36m
  • Airport Perugia: 137km - 1h 40m
The nearest local amenities:
  • Castellina in Chianti: 5km - 0h 09m
  • Ambra: 8km - 0h 15m
  • Castellina Scalo: 15km - 0h 17m
The closest town with shops to Tregole is Castellina in Chianti, which is 5km away. This market town also has a good selection of restaurants.

Guest reviews: Tregole

5/5 Score from 3 reviews - Superb (3 Client reviews)
Jane
July 2023
Group of friends
Warrington, United Kingdom Warrington, United Kingdom
Guest villa score
5/5
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!
Local attractions 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 !

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Any duration

Duration (weeks)

Any size

Number of Guests

adults Ages 16+

children Ages 2 - 15

infants Under 2


7 nights from
$6,527 to $10,044

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