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Villa Tregole

Castellina in Chianti - Siena and Chianti

14 7 7 Private Pool
Villa Tregole is a charming stone-built country house in the heart of Chianti Classico, surrounded by olive groves, vineyards, and the rolling hills of Tuscany. Located on the renowned Tregole winery, it’s ideal for families or groups seeking peace, privacy, and an authentic Tuscan experience.

The villa’s central location makes it a perfect base for exploring the region’s wineries, castles, and hilltop villages. The osteria of the nearby Castello di Fonterutoli is just minutes away by car or a scenic walk. Castellina in Chianti, with shops, cafés, and the excellent Gelateria di Castellina, is a short drive. Siena, San Gimignano, Florence, and Arezzo are also within easy reach.

Set in a quiet rural area, the villa is surrounded by well-kept gardens with mature trees. Multiple terraces and outdoor seating areas offer both sun and shade, and the large pool is perfect for relaxing.

The house includes a main villa and two separate apartments, each with its own entrance. The main villa features four upstairs bedrooms and a spacious open-plan kitchen, dining, and living area on the ground floor, opening onto a covered terrace. The two apartments each have a kitchen and living-dining area; one with two bedrooms, the other with a ground-floor bedroom.

Interiors combine terracotta floors, wood-beamed ceilings, and soft-toned décor for a warm, elegant feel.

The Tregole winery offers guided tours and tastings. A private cook can prepare Tuscan meals or pizza evenings on request. The discreet owners live next door and are happy to assist if needed.

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

4 Jul 2026 - 5 Sep 2026

7,440 Euro

5 Sep 2026 - 19 Sep 2026

5,580 Euro

19 Sep 2026 - 7 Nov 2026

4,835 Euro

7 Nov 2026 - 12 Dec 2026

4,835 Euro

12 Dec 2026 - 2 Jan 2027

5,435 Euro

2 Jan 2027 - 22 May 2027

5,435 Euro

22 May 2027 - 3 Jul 2027

6,200 Euro

3 Jul 2027 - 4 Sep 2027

8,090 Euro

4 Sep 2027 - 25 Sep 2027

6,200 Euro

25 Sep 2027 - 1 Jan 2028

5,435 Euro

Villa Facilities

Flexible dates
Washing Machine
Air-conditioning
Internet
Carbon Monoxide Detector

Villa Floor Plans

Good To Know

Usage to pay on-site: Heating Villa, Air Conditioning, EV charge point
Tourist tax: 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 !