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Villa Delle Upupe
Castellina in ChiantiCastellina in Chianti·Siena
From € 930,00 /night
Property Type:  Independent Villa

Cod: ESR 11
200 m²
House
300 m²
Land
7
Rooms
8
Sleeps
4
Bedrooms
5
Bathrooms
From € 930,00 /night
200 m²
House
300 m²
Land
7
Rooms
8
Sleeps
4
Bedrooms
5
Bathrooms

About the property

Villa delle Upupe is located approximately 2 km from the borgo of Castellina in Chianti, in the hilly green countryside between Siena and Florence in the heart of Chianti Classico, a beautiful region famous throughout the world for its picture-postcard views and for the excellence of its wines. It enjoys a privileged position on top of a hill, overlooking the beautiful landscape dotted with olive trees and vines and is surrounded by dense wooded vegetation, ideal for taking long walks in close contact with nature.

Discover the Villa
Inside the exposed stone exterior is a fascinating interior: every room, from the warm intimate bedrooms to the cosy living area, has been designed with great attention to detail, with fine furnishings and accessories, combined with beautiful upholstery that recalls the unmistakable hues of the Sienese countryside. The result of shrewd restoration, this farmhouse reinterprets classic Tuscan architecture, adapting to the sloping terrain due to which both floors have outside access, especially on the lower floor where the brightly-lit rooms of the living area open out to the private garden, an authentic corner of tranquillity enriched by an attractive pergola for relaxing outdoors and by a beautiful swimming pool nestling in the vineyards that produce one of the finest wines in Chianti Classico. We are, in fact, within the Castellare di Castellina, a prestigious and well established farm estate which covers an area of about 80 hectares and which produces excellent extra virgin olive oil and some of the most select wines of Chianti. The winery, open for tasting and for the sale of wine and olive oil, is about 2 km from the farmhouse. Not far from the property is the scenic Chiantigiana, a panoramic bridge that connects Siena to Florence, which you can take to make day trips to the well-known localities of Radda, Gaiole, Greve and Panzano, rich in art treasures, churches and Renaissance villas perched on scenic hills. N.B. The house has a separate entrance and is about 50 m from the owners' villa from which it is separated by hedge screens to ensure maximum privacy.

 

VILLA DELLE UPUPE HAS BEEN SUBJECTED TO A CHECK-UP BY A TECHNICAL RESPONSIBLE BEFORE THE BEGINNING OF THE SEASON, TO ENSURE CONSISTENCY OF THE DESCRIPTION, ACCESSORIES LISTED ON THIS PAGE AND THEIR PRESENT STATE OF OPERATION/MAINTENANCE, TO GUARANTEE QUALITY, CLEANLINESS AND COMFORTS TO ALL CLIENTS WHO WILL STAY HERE.

 

Interior:

The house has two floors which follow the natural slope of the terrain and are connected by both internal and external staircases. The main entrance is on the ground floor which is composed of two double bedrooms and one twin bedroom, all with private bathrooms (two with shower and one with tub and shower). Going down to the lower floor, you come to an elegant living room with ornamental fireplace and the dining room, both facing the back garden. From the dining room, a few steps lead down to the kitchen and to a room used as both pantry and laundry. This floor is completed by a bedroom (with double divisible bed) with ensuite bathroom with shower and a toilet.

 

Park:

The house is surrounded by a peaceful garden that adapts to the sloping surface of the property and is one with the beautiful setting of vineyards, woods and hills that delimit it naturally. The vegetation composed of lavender bushes, wild roses, jasmine, strawberry trees, herbs and borders of rosemary, which frame the dry stone walls and short stone paths, is the backdrop to the panoramic pergola just outside the living room French windows and to the exclusive pool, the perfect spot from which to admire the beautiful sunset over the Chianti hills.Please notice that photos are taken in spring, therefore flower blossoming, and the colours of the gardens' grass could be different at the moment of your arrival at the villa.

 

Swimming Pool:

The rectangular-shaped swimming pool is located behind the villa, on lower terracing, and is reached down a few steps near the pergola. Lined in grey PVC, it measures 3 x 9 m with the depth ranging from 1.40 to 1.60 m and fits perfectly into the natural landscape that surrounds it. There are three steps for easy access to the water and it has chlorine purification. The sunbathing area, in part paved in stone around the pool and in part lawn, is provided with sunbeds and umbrellas and is bounded on one side by dry stone walls and on the other by a thick screen of vines. There is also a cold-water shower. The pool will be available from the last Saturday in April to the first Saturday in October.

Features

Swimming pool
Private garden
Private parking
Pet friendly
Air Conditioning
Wi-Fi

Location

Nearby

  • Florence: Approximately 50 kilometers (31 miles).
  • Rome: Approximately 250 kilometers (155 miles).
  • Milan: Approximately 330 kilometers (205 miles).
  • Naples: Approximately 450 kilometers (280 miles).
  • Venice: Approximately 300 kilometers (186 miles).
  • Turin: Approximately 400 kilometers (248 miles).
  • Bologna: Approximately 120 kilometers (75 miles).
  • Pisa: Approximately 100 kilometers (62 miles).
  • Genoa: Approximately 260 kilometers (162 miles).
  • Siena: Approximately 20 kilometers (12 miles).

Places of interest

Castellina in Chianti is a picturesque village located in the heart of the Chianti region in Tuscany, known for its rich history, charming medieval architecture, and stunning views of vineyards and olive groves. The area is famous for its wine production, particularly Chianti Classico, and offers a wealth of attractions for visitors interested in history, culture, and gastronomy. Here are some points of interest in and around Castellina in Chianti:

  • Rocca di Castellina: A historic 14th-century fortress with a panoramic tower that houses the Museo Archeologico del Chianti Senese, displaying Etruscan, Roman, and medieval artifacts.
  • Via delle Volte: An ancient underground street running along the medieval walls of Castellina. Today, it’s a charming pedestrian path lined with shops, restaurants, and artisan workshops.
  • Church of San Salvatore: A medieval church in the town center, known for a 15th-century wooden crucifix and its simple yet elegant design.
  • Etruscan Tomb of Montecalvario: An ancient Etruscan tomb from the 6th century BC located just outside Castellina, consisting of four burial chambers around a central mound.
  • Castello di Fonterutoli: A historic estate and winery near Castellina, owned by the Mazzei family since 1435. The estate offers tours, wine tastings, and stunning views of the vineyards.
  • Castello di Brolio: An ancient castle near Gaiole in Chianti, known for producing Chianti Classico wine and its historical significance in the region.
  • Pieve di San Leonino: An 11th-century Romanesque church near Castellina, renowned for its architecture and ancient interior frescoes.
  • Chianti Sculpture Park: An outdoor contemporary art museum in Pievasciata, featuring sculptures by international artists integrated into the natural landscape.
  • Greve in Chianti: A charming town in Chianti, famous for its main square, Piazza Matteotti, surrounded by wine bars, and the annual Chianti Classico Wine Festival.
  • Radda in Chianti: A hilltop village near Castellina with a well-preserved historic center, including the Palazzo del Podestà and the Church of San Niccolò.
  • Panzano in Chianti: A village near Castellina, famous for the butcher shop of Dario Cecchini and its scenic views of the Chianti countryside.
  • Badia a Passignano: A historic abbey near Tavarnelle Val di Pesa, surrounded by vineyards, known for the monks' wine production and serene atmosphere.
  • Val d'Elsa: A nearby valley with rolling hills, medieval towns, and scenic landscapes, including towns like San Gimignano, Monteriggioni, and Colle di Val d'Elsa.
From € 930,00 /night

Price Table

April 2026
€ 862.00
Price per day (Minimum stay: 5 nights)
May 01st - 23rd, 2026
€ 997.50
Price per day (Minimum stay: 5 nights)
May 23rd - June 27th, 2026
€ 1,223.00
Price per day (Minimum stay: 5 nights)
June 27th - Aug. 29th, 2026
€ 1,429.00
Price per day (Minimum stay: 5 nights)
Aug. 29th - Sept. 26th, 2026
€ 1,223.00
Price per day (Minimum stay: 5 nights)
October 2026
€ 862.00
Price per day (Minimum stay: 5 nights)

Get in touch

Things to know

Minimum stay: 5
Check in: 04.00 pm
Check in: 10.00 am
users
Maximum guests: 8
Pets allowed

Policy

ALL FEATURES

BATHROOM

Shower
Bathtub
Toiletries
Hair dryer
Washer
Iron

ENTERTEINMENT

Cable / Satellite TV

FAMILY

Crib
High chair

HEATING & AIR CONDITIONING

Air conditioning
Floor heating
Floor cooling
Fireplace
Mosquito nets

INTERNET & WORKSPACE

Wi-Fi

KITCHEN & DINING ROOM

Refrigerator
Oven
Microwave
Dish & Silverware
Dishwasher
Coffee maker

PROPERTY CARACTERISTICS

Private parking
Private garden
    Pet friendly

OUTDOOR

Patio
Garden backyard
Outdoor furniture
Swimming pool

SERVICES

Flexible check-in and check-out

Price Includes

Price not Includes

  • Mandatory extra cleaning in case of animals (€ 50,00/week or part of week/animal)
  • Tourism tax (€ 2,00 per person per day for the first 7 days. Please note that children under 14 years old will not pay).

Extra Services

  • extra cleaning (€ 22,00/hour/cleaner), extra linen change (€ 15,00 per person),
  • Home Chef
  • Experiences

Booking & Cancellation

To book this villa, please contact us to confirm availability for your desired dates.
Once the availability of the dates has been confirmed, you will receive a quote. you will have to pay 30% of the deposit + any management fees and policies, the balance must be paid no later than 60 days before check in. In the case of an "underdated" booking, i.e. a delay of less than 60 days between the booking date and the start date of the stay, the payment required will be 100%

Cancellation of a reservation, even if replaced by another, involves the payment of the following penalties:

30% of the total booking price (rental price relating to the booking period) plus EV booking fees in the case of booking cancellation communicated before (and no later than) the 60th day from the start of the stay;

60% of the total booking price (rental price relating to the booking period) plus EV booking fees in the case of booking cancellation communicated between the 59th and 30th day from the start of the stay;

80% of the total booking price (rental price relating to the booking period) plus EV booking fees in the case of booking cancellation communicated between the 29th and 15th day from the start of the stay;

100% of the total booking price (rental price relating to the booking period) plus EV booking fees in the case of booking cancellation communicated within 14 days before the start of the stay.

* In case of cancellation of the booking for justified reasons, these penalties are covered by the EuropAssistance insurance policy signed at the time of booking, as regulated by the "Cancellation Insurance Conditions".

**The “Booking Fees” are never refundable.

Get in touch

Get in touch

EXTRA SERVICES

  • extra cleaning (€ 22,00/hour/cleaner), extra linen change (€ 15,00 per person),
  • Home Chef
  • Experiences

Search your dream House

Category
Tipologia
Price
Price
Surface
Superficie
Bed
Camere da Letto New
Bathroom
Bagni New

Ameneties

Svimming pool
Aria condizionata
Parcheggio privato
Giardino privato
Riscaldamento

About this space

Castellina in Chianti is a picturesque village located in the heart of the Chianti region in Tuscany, known for its rich history, charming medieval architecture, and stunning views of vineyards and olive groves. The area is famous for its wine production, particularly Chianti Classico, and offers a wealth of attractions for visitors interested in history, culture, and gastronomy. Here are some points of interest in and around Castellina in Chianti:

  • Rocca di Castellina: A historic 14th-century fortress with a panoramic tower that houses the Museo Archeologico del Chianti Senese, displaying Etruscan, Roman, and medieval artifacts.
  • Via delle Volte: An ancient underground street running along the medieval walls of Castellina. Today, it’s a charming pedestrian path lined with shops, restaurants, and artisan workshops.
  • Church of San Salvatore: A medieval church in the town center, known for a 15th-century wooden crucifix and its simple yet elegant design.
  • Etruscan Tomb of Montecalvario: An ancient Etruscan tomb from the 6th century BC located just outside Castellina, consisting of four burial chambers around a central mound.
  • Castello di Fonterutoli: A historic estate and winery near Castellina, owned by the Mazzei family since 1435. The estate offers tours, wine tastings, and stunning views of the vineyards.
  • Castello di Brolio: An ancient castle near Gaiole in Chianti, known for producing Chianti Classico wine and its historical significance in the region.
  • Pieve di San Leonino: An 11th-century Romanesque church near Castellina, renowned for its architecture and ancient interior frescoes.
  • Chianti Sculpture Park: An outdoor contemporary art museum in Pievasciata, featuring sculptures by international artists integrated into the natural landscape.
  • Greve in Chianti: A charming town in Chianti, famous for its main square, Piazza Matteotti, surrounded by wine bars, and the annual Chianti Classico Wine Festival.
  • Radda in Chianti: A hilltop village near Castellina with a well-preserved historic center, including the Palazzo del Podestà and the Church of San Niccolò.
  • Panzano in Chianti: A village near Castellina, famous for the butcher shop of Dario Cecchini and its scenic views of the Chianti countryside.
  • Badia a Passignano: A historic abbey near Tavarnelle Val di Pesa, surrounded by vineyards, known for the monks' wine production and serene atmosphere.
  • Val d'Elsa: A nearby valley with rolling hills, medieval towns, and scenic landscapes, including towns like San Gimignano, Monteriggioni, and Colle di Val d'Elsa.

Aabout this Space

Villa delle Upupe is located approximately 2 km from the borgo of Castellina in Chianti, in the hilly green countryside between Siena and Florence in the heart of Chianti Classico, a beautiful region famous throughout the world for its picture-postcard views and for the excellence of its wines. It enjoys a privileged position on top of a hill, overlooking the beautiful landscape dotted with olive trees and vines and is surrounded by dense wooded vegetation, ideal for taking long walks in close contact with nature.

Inside the exposed stone exterior is a fascinating interior: every room, from the warm intimate bedrooms to the cosy living area, has been designed with great attention to detail, with fine furnishings and accessories, combined with beautiful upholstery that recalls the unmistakable hues of the Sienese countryside. The result of shrewd restoration, this farmhouse reinterprets classic Tuscan architecture, adapting to the sloping terrain due to which both floors have outside access, especially on the lower floor where the brightly-lit rooms of the living area open out to the private garden, an authentic corner of tranquillity enriched by an attractive pergola for relaxing outdoors and by a beautiful swimming pool nestling in the vineyards that produce one of the finest wines in Chianti Classico. We are, in fact, within the Castellare di Castellina, a prestigious and well established farm estate which covers an area of about 80 hectares and which produces excellent extra virgin olive oil and some of the most select wines of Chianti. The winery, open for tasting and for the sale of wine and olive oil, is about 2 km from the farmhouse. Not far from the property is the scenic Chiantigiana, a panoramic bridge that connects Siena to Florence, which you can take to make day trips to the well-known localities of Radda, Gaiole, Greve and Panzano, rich in art treasures, churches and Renaissance villas perched on scenic hills. N.B. The house has a separate entrance and is about 50 m from the owners' villa from which it is separated by hedge screens to ensure maximum privacy.

 

VILLA DELLE UPUPE HAS BEEN SUBJECTED TO A CHECK-UP BY A TECHNICAL RESPONSIBLE BEFORE THE BEGINNING OF THE SEASON, TO ENSURE CONSISTENCY OF THE DESCRIPTION, ACCESSORIES LISTED ON THIS PAGE AND THEIR PRESENT STATE OF OPERATION/MAINTENANCE, TO GUARANTEE QUALITY, CLEANLINESS AND COMFORTS TO ALL CLIENTS WHO WILL STAY HERE.

 

Interior:

The house has two floors which follow the natural slope of the terrain and are connected by both internal and external staircases. The main entrance is on the ground floor which is composed of two double bedrooms and one twin bedroom, all with private bathrooms (two with shower and one with tub and shower). Going down to the lower floor, you come to an elegant living room with ornamental fireplace and the dining room, both facing the back garden. From the dining room, a few steps lead down to the kitchen and to a room used as both pantry and laundry. This floor is completed by a bedroom (with double divisible bed) with ensuite bathroom with shower and a toilet.

 

Park:

The house is surrounded by a peaceful garden that adapts to the sloping surface of the property and is one with the beautiful setting of vineyards, woods and hills that delimit it naturally. The vegetation composed of lavender bushes, wild roses, jasmine, strawberry trees, herbs and borders of rosemary, which frame the dry stone walls and short stone paths, is the backdrop to the panoramic pergola just outside the living room French windows and to the exclusive pool, the perfect spot from which to admire the beautiful sunset over the Chianti hills.Please notice that photos are taken in spring, therefore flower blossoming, and the colours of the gardens' grass could be different at the moment of your arrival at the villa.

 

Swimming Pool:

The rectangular-shaped swimming pool is located behind the villa, on lower terracing, and is reached down a few steps near the pergola. Lined in grey PVC, it measures 3 x 9 m with the depth ranging from 1.40 to 1.60 m and fits perfectly into the natural landscape that surrounds it. There are three steps for easy access to the water and it has chlorine purification. The sunbathing area, in part paved in stone around the pool and in part lawn, is provided with sunbeds and umbrellas and is bounded on one side by dry stone walls and on the other by a thick screen of vines. There is also a cold-water shower. The pool will be available from the last Saturday in April to the first Saturday in October.