Entire home
Villa Tregole, Castellina in Chianti, Siena and Chianti
Castellina in Chianti villa with private pool
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Reviews
1010 out of 10
Exceptional
Entire home
Popular amenities
- Pool
- Kitchen
- Washer
- Air conditioning
- Outdoor Space
- Barbecue grill
Explore the area

Castellina in Chianti, Siena and Chianti
- Piazza di Santa Maria NovellaPlace, Piazza di Santa Maria Novella
- Cathedral of Santa Maria del FiorePlace, Cathedral of Santa Maria del Fiore
- Ponte VecchioPlace, Ponte Vecchio
- Florence (FLR-Peretola)Airport, Florence (FLR-Peretola)
Room options
About the area
Castellina in Chianti
In Castellina in Chianti .Within 3 miles (5 km) of this Castellina in Chianti villa, you'll find Mazzei Winery and Walls of Monteriggioni. Archaeological Museum of Chianti and City Hall Castellina In Chianti are also within 3 miles (5 km).
Getting around
- Monteriggioni Badesse Station - 15 min drive
- Florence Airport, Peretola (FLR) - 56 min drive
Restaurants
- Dievole Wine Resort - 27 min drive
- Osteria Il Re Gallo - 10 min drive
- Albergo Casafrassi - 12 min drive
- Taverna di Vagliagli - 22 min drive
- Taverna Squarcialupi - 11 min drive
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
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
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Property amenities
Pool/Spa
- Private pool
Internet
- Available in the villa: Internet access
Kitchen
- Coffee/tea maker
- Cookware, dishware, and utensils
- Dishwasher
- Microwave
- Oven
- Refrigerator
- Stovetop
Bedrooms
- 7 bedrooms
- Bedsheets provided
Bathroom
- 7 bathrooms
- Hair dryer
- Towels provided
Living spaces
- Fireplace
- Living room
Entertainment
- TV
Outdoor areas
- Barbecue grill
- Garden
Laundry
- Laundry facilities
- Washing machine
Work spaces
- Desk
Comfort
- Air conditioning
Pets
- No pets allowed
Suitability/Accessibility
- Smoking not allowed
Location highlights
- In a rural location
Things to do
- Cycling nearby
Safety features
- Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
- Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)
General
- Garden
- Unit size: 5,382 square feet
Policies
Check-in
Check-in time starts at 4:00 PM
Minimum check-in age: 18
Check-out
Check-out before 10:00 AM
Special check-in instructions
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Rules
Tourist tax: 1.50 € per person, per night for the first 7 nights, some exemptions apply.
High chair: 2 available on request, no extra cost
Baby: 2 available on request, no extra cost
Charged based on usage: Heating Villa, Air Conditioning, EV charge point
Final clean: included - provided by local supplier
Pets
- No pets allowed
Children and extra beds
- Children are welcome.
Events
No events 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
Onsite 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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
- This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. Onsite parties or group events are strictly prohibited.
Property Registration Number IT052005B5RPP9LFRY
We should mention
- All guests (including children) need to be present at check-in to show their government-issued photo ID or passport.
- Onsite cash transactions can't exceed EUR 5000, due to national regulations. For more details, please contact the property using information in the booking confirmation.
Property is also known as
1454A