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Villa Tregole, Castellina in Chianti, Siena and Chianti
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Reviews
10 out of 10
Exceptional
7 bedrooms7 bathroomsSleeps 14500 sq m
Popular amenities
Explore the area

Castellina in Chianti, Siena and Chianti
- City Hall Castellina In Chianti8 min drive
- Mazzei Winery8 min drive
- Walls of Monteriggioni9 min drive
- Siena (SAY-Ampugnano)38 min drive
Rooms & beds
7 bedrooms (sleeps 14)
7 bathrooms
Bathroom 1
Bathroom 2
Bathroom 3
Bathroom 4
Bathroom 5
Bathroom 6
Bathroom 7
Spaces
Kitchen
Garden
About this property
Villa 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, 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
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
Property manager
To Tuscany
Premier Host
Languages
English
Add dates for prices
Amenities
Pool
Kitchen
Washer
Air conditioning
Outdoor space
Barbecue grill
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House Rules
Check in after 4:00 PM
Minimum age to rent: 18
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets allowed
Smoking
Smoking is not permitted
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
Property Registration Number IT052005B5RPP9LFRY
We should mention
All guests, including children, must be present at check-in and show their government-issued photo ID card or passport
Cash transactions at this property cannot exceed EUR 5000, due to national regulations; for further details, please contact the property using the information in the booking confirmation
About the area
Castellina in Chianti
Located in Castellina in Chianti, this villa is in a rural area. Castellina Fortress and Walls of Monteriggioni are local landmarks, and some of the area's activities can be experienced at Mazzei Winery and Casa Vinicola Luigi Cecchi. Looking to enjoy an event or a game while in town? See what's happening at Palasport Mens Sana or Siena Stadium.

Castellina in Chianti, Siena and Chianti
What's nearby
- City Hall Castellina In Chianti - 8 min drive - 4.9 km
- Mazzei Winery - 8 min drive - 2.5 km
- Casa Vinicola Luigi Cecchi - 9 min drive - 5.1 km
- Walls of Monteriggioni - 9 min drive - 6.0 km
- Monteriggioni Castle - 22 min drive - 16.9 km
Getting around
Restaurants
- Bar Italia - 8 min drive
- Ristorante Albergaccio di Castellina - 10 min drive
- Taverna Squarcialupi - 9 min drive
- Tre Porte - 9 min drive
- Made in Chianti - 10 min drive
Frequently asked questions
Reviews
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About the host
Hosted by To Tuscany

Languages:
English
Premier Host
They consistently provide great experiences for their guests
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