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Castellina In Chianti Luxury Holiday Rentals

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    Travellers to Castellina In Chianti are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    27 Matching Rentals in Castellina In ChiantiView all 183 rentals
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    15 Bedrooms, 15 Bathrooms, Sleeps 33 Quick View
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    7 Bedrooms, 9 Bathrooms, Sleeps 14 Quick View
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    Vrijstaande villa met zwembad en pizzaoven voor acht personen.1 / 29
    (5)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Central Heating
    • Patio
    • Private Outdoor Pool (Unheated)
    • Mountain Views
    • Washer
    • Wi-Fi
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 August 2016
    This house is really something. Conveniently located between Siena, Florence and Pisa I don't think you would find a finer spot in Tuscany. And the place itself: fantastic. You...
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    53011, Castellina In Chianti, Province of Siena
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 8
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    Studio, 5 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
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    • Cable/satellite TV
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    • Central Heating
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This large, stone-built farmhouse, dating back to the 16th century, is located on a well-known wine estate near Siena. The estate produces Chianti Classico wines. Ideal for a large family, this six bedroom farmhouse is built around an internal courtyard and is fully equipped with modern amenities...
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    53011, Castellina In Chianti, Province of Siena
    Holiday Rental House - 5 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    About this property
    Villa Gaiole features all the comforts and a wonderful panoramic Tuscan Villa in Chianti between Siena and Florence, with private pool, air conditioning, total privacy, and a lovely park.
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    53013, Castellina In Chianti, Province of Siena
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    La Corte di Campalli1 / 28
    (3)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
    • Housekeeping Included
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    • Balcony
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    • Terrace
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    Pet friendly
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    Reviewed 8 July 2018
    There cannot be a more beautiful place in Tuscany — or anywhere for that matter. This historic property is surrounded by hills and vineyards that one sees in paintings of...
    Reviewed 7 January 2013
    Our children have grown up withing the walls of Corte di Campalli. It is the perfect villa to share with family, freinds, young and old. My 88 year old grandmother even...
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    About this property
    Whether you’re a connoisseur of wine or simply enjoy a glass with dinner, a stay at La Corte di Campalli in Chianti is an unforgettable experience. Located on a large wine estate, the six-bedroom farmhouse was built in the 16th century and restored in 2002. The property offers an up-close look at...
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    50050, Fonterutoli, Castellina In Chianti
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    6 Bedroom Countryside Villa with Expansive Views1 / 36
    (4)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Central Heating
    • Grill
    • Private Outdoor Pool (Unheated)
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    • Cable/satellite TV
    • Patio
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 August 2014
    I stayed with my family at this beautiful villa. The setting is lovely on a hilltop, set amongst an active farm of olive trees and many vines. It was very helpful to have Elvira...
    Reviewed 22 October 2013
    My husband & I were 2 of 10 friends that stayed at this beautiful villa for a week in September. Simonetta & her family welcomed us with open arms & wonderful cheese...
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    About this property
    This beautiful property belongs to the Campalli estate, a huge farm of 750 acres that produces Chianti Classico wine, and includes the Castle of Campalli.The 360° view from each point on the estate ranges over endless rolling hills, vineyards and olive groves. On a clear day it is possible to see...
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    53011, Fonterutoli, Castellina In Chianti
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    6 Bedrooms, 5 Bathrooms, Sleeps 13 Quick View
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    • Washer
    • Cable/satellite TV
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Set in the heart of the magical Chianti Classico region, this wonderful 6 BD – 5 BA Villa dates back to the 15th century and is strategically located with a short distance from the lively village of Castellina in Chianti. Surrounded by an exceptionally beautiful landscape, the property is perfect...
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    53011, Castellina In Chianti, Province of Siena
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 13
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    8 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • Washer
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    Pet friendly
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    About this property
    Owner's description: Main Description : Casale il Poggino, located in a hilly position in the heart of the Chianti Classico, consists of two units, the farmhouse which is divided into three apartments (for 14 people) communicating with each other from the outside and the annex (for 02 people)...
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    53011, Fonterutoli, Castellina In Chianti
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 16
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    8 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • Internet Access
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    About this property
    Owner's description: Outside this property, located in a hilly position in the heart of the Chianti Classico, consists of two units, the farmhouse which is divided into three apartments (for 14 people) communicating with each other from the outside and the annex (for 02 people) country house 'this...
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    53011, Fonterutoli, Castellina In Chianti
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 16
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    Villa Delle Upupe 81 / 48
    (1)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Mountain Views
    • Private Outdoor Pool (Unheated)
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    • Secure Parking
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 June 2017
    We stayed in the villa for 15 days and enjoyed every moment. The house is spacey, comfortable, clean and has a good atmosphereThe garden and pool are phenomenal, the views are...
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    About this property
    RECEPTIVE STRUCTURE. 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...
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    53011, Castellina In Chianti, Province of Siena
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    About this property
    Villa Lucia in Chianti is right in the heart of Tuscany, the ideal location for exploring the region and has a beautiful formal Italian garden and a private pool. A whole range of activities can be organized to make your stay extra special.
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    50021, Castellina In Chianti, Province of Siena
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Villa Patrignone 7 bedroom Tuscany villa with pool1 / 24
    (2)Excellent
    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Patio
    • Grill
    • Balcony
    • Mountain Views
    • Wi-Fi
    • Secure Parking
    • Shared Outdoor Pool (Unheated)
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 October 2014
    Our hosts, Simon and Verity, were marvels of hosting. They made sure we were comfortable and knew the ins and outs. They were hospitable without being intrusive. A true skill...
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    About this property
    Villa Patrignone has 7 large double bedrooms, each with private bathroom, a cavernous kitchen-dining room with large fireplace, and a lovely living room, with high vaulted ceilings, comfortable sofas and a library. The house was built sometime in the 1500s and still has most of its original...
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    53011 SI, Castellina In Chianti, Province of Siena
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    Villa Patrignone - a beautiful large Tuscany Villa1 / 38
    (26)Excellent
    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Internet Access
    • Balcony
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Mountain Views
    • Patio
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 September 2018
    Nine of us, four children and five adults, just returned from an Italian adventure of a lifetime. The highlight of our trip (agreed by all) was a wonderful week at Podere...
    Reviewed 4 June 2016
    Our family stayed in the main villa for 11 days at the beginning of August. We rented 6 of the 7 bedrooms for our wide-ranging group (a baby, 2 eight-year olds, a teen, 2 in...
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    About this property
    Villa Patrignone has 7 large double bedrooms, each with private bathroom, a cavernous kitchen-dining room with large fireplace, and a lovely living room, with high vaulted ceilings, comfortable sofas and a library. The house was built sometime in the 1500s and still has most of its original...
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    53011, Castellina In Chianti, Province of Siena
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    5 Bedrooms, 3 Bathrooms, Sleeps 15 Quick View
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    • Wi-Fi
    • Washer
    • Central Heating
    • Mountain Views
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Cable/satellite TV
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    View all property information
    Location Information
    53011, Castellina In Chianti, Province of Siena
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 15
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    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Internet Access
    • Grill
    • Air Conditioning
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description: Pool will be open on: 27 Apr 2018 22:00:00 \r\nPool will be close on: 28 Sep 2018 22:00:00 \r\nCleaning is from Monday to Friday (also on Saturday for stays longer than 1 week). Internet wi-fi. Villa Belvedere is a large and attractive stone farmhouse, lying within the old...
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    53011, Castellina In Chianti, Province of Siena
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Air Conditioning
    • Parking
    • Washer
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The villa in Chianti (400 m2) was built in the early 16th century as an ancient oratory. In 1876 it underwent its first transformation into a farmhouse and only today, thanks to a skilful restoration project that brought the structure back to its original beauty, a country villa rental has been...
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    53011, Castellina In Chianti, Province of Siena
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Farmhouse Rental in Chianti Area of Tuscany - Villa Adelina1 / 46
    (7)Very good
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Central Heating
    • Private Outdoor Pool (Unheated)
    • Washer
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the heart of the Chianti, this farmhouse is situated on a beautiful and renowned wine estate that offers more than the typical Tuscan experience. Not only are there panoramic views of the rolling hills covered with vineyards and olive groves, but there is also the perk of being able to...
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    53011, Castellina In Chianti, Province of Siena
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    Farmhouse Rental in Chianti Area of Tuscany - Casa Luciana1 / 26
    (18)Excellent
    5 Bedrooms, 7 Bathrooms, Sleeps 10 Quick View
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    • Central Heating
    • Cable/satellite TV
    • Grill
    • Washer
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 June 2013
    I rented this villa for a week so that my we could share Italy with my kids, their spouses and their young children. We needed a place with adequate bedrooms and bathrooms. Casa...
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    About this property
    Located in the heart of the Chianti, this farmhouse is situated on a beautiful and renowned wine estate that offers more than the typical Tuscan experience. Not only are there panoramic views of the rolling hills covered with vineyards and olive groves, but there is also the perk of being able to...
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    Location Information
    53011, Castellina In Chianti, Province of Siena
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 10
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    5 Bedrooms, 7 Bathrooms, Sleeps 10 Quick View
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    About this property
    Owner's description: Large stone-built farmhouse (480 m2) completely restored farmhouse, situated inside a large property which covers an area of about 460 hectares near Castellina in Chianti in a peaceful and panoramic position amidst the vineyards and gently rolling hills of Chianti Classico...
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    53011, Castellina In Chianti, Province of Siena
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description: The villa in Chianti (400 m2) was built in the early 16th century as an ancient oratory. In 1876 it underwent its first transformation into a farmhouse and only today, thanks to a skilful restoration project that brought the structure back to its original beauty, a country...
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    Location Information
    53011, Fonterutoli, Castellina In Chianti
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Air Conditioning
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description: Main Description : The Capanna Leopoldina, dating back to the first half of the 18th century as marked on the first Tuscan land register, has been completely restored and now offers 5 bedrooms and 5 bathrooms, while maintaining its typical Tuscan style with wood beamed ceilings...
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    53011, Castellina In Chianti, Province of Siena
    Condo/Apartment - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Balcony
    • Grill
    • Patio
    • Central Heating
    • Housekeeping Included
    • Terrace
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    From 2017 for the months of May and June only we are offering the entire main building of Le Ripe which includes the Stalle, the Loggia and the Main house, where we live during the rest of the year. While guests stay in the main building your hosts will lodge in the nearby Fienile. This special...
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    53011, Castellina In Chianti, Province of Siena
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description: Historical 18th Century villa with outbuilding, on two floors, 340 sq. m. with 5 double bedrooms and 4 bathrooms capable of holding up to 10 persons. The villa has a large terraced and enclosed park with a private swimming pool, an outdoor eating area with stonework barbecue,...
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    53011, Castellina In Chianti, Province of Siena
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, 7 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Air Conditioning
    • Grill
    • Parking
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Large stone-built farmhouse (480 m2) completely restored farmhouse, situated inside a large property which covers an area of about 460 hectares near Castellina in Chianti in a peaceful and panoramic position amidst the vineyards and gently rolling hills of Chianti Classico (350 m a.s.l.) between...
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    53011, Castellina In Chianti, Province of Siena
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 10
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    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
    • Grill
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description: Main Description : Beautiful stone holiday home set on a hilltop in the heart of the Chianti Classico region and a mere 5km form the charming town of Castellina in Chianti. This very spacious property will delight guests by its level of comfort despite being hundreds of years...
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    53011, Castellina In Chianti, Province of Siena
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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