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155 Holiday homes

Travellers going to Castellina In Chianti are booking September dates now. Secure your holiday home today and have the perfect trip.

1 / 100

Castellina - small - Castellina In Chianti apartment sleeps 2

Province of Siena / Castellina In Chianti

1 bedroomSleeps 23 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Swimming pool; Great for children of all ages ; No pets allowed;
These apartments are ideal for a romantic escape in Tuscany. Both apartments comes with fire burning fireplace, a small but refined living room with sofa bed an equipped kitchenette and a double king size bedroom and bathroom with shower. Both apartments have windows op  …see more

from £95 / night

£665 - £940 / week

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from £95 / night

1 / 100

Castellina - middle - Castellina In Chianti apartment sleeps 5

Province of Siena / Castellina In Chianti

2 bedroomsSleeps 53 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min stay
Key info: Swimming pool; Great for children of all ages ; No pets allowed;
Some of the middle  size apartments are located in the old school for children of the hamlet while some others are located in the old house of the estate ranger and in the oldest building of the farm called Darios House. All middle size apartment two double bedroom  …see more

from £101 / night

£706 - £1010 / week

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from £101 / night

(2) Excellent 

1 / 48

Province of Siena / Castellina In Chianti

2 bedroomsSleeps 44 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min stay
Key info: Nearest beach 150 km; Great for children of all ages ; Car essential;
 …see more

from £100 / night

£459 - £542 / week

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from £100 / night

(1) Excellent 

1 / 12

Villa Masseto - Castellina In Chianti villa sleeps 10

Province of Siena / Castellina In Chianti

5 bedroomsSleeps 107 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
Beautiful independent restored villa (400 sqm) sleeping 10 with private pool, astro turf tennis court, daily maid service, gardens. Located in panoramic position on a Chianti Hillside only 5km from Castellini in Chianti. The private swimming pool (6/10m) is situated on  …see more

from £393 / night

£2750 - £3167 / week

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from £393 / night

(2) Very Good 

1 / 100

Castellina In Chianti 81687 - Castellina In Chianti villa sleeps 10

Province of Siena / Castellina In Chianti

5 bedroomsSleeps 10Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
The villa dating back to the first 800 as is present in the Catasto Leopoldino (the first inventory in Tuscany), it has been restructured maintaining it Tuscan typical style with ceilings with beams in wood and floors in cooked and window "mandorlate" that the  …see more

from £327 / night

£1910 - £2862 / week

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from £327 / night

(1) Very Good 

1 / 30

Province of Siena / Castellina In Chianti

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; No pets allowed;
 …see more

from £58 / night

£462 - £1438 / week

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from £58 / night

1 / 100

Castellina In Chianti 48549 - Castellina In Chianti villa sleeps 8

Province of Siena / Castellina In Chianti

5 bedroomsSleeps 87 nights min stay

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
Beautiful stone farmhouse with private pool situated in quiet and panoramic location. This villa is nestling deep amidst the Chianti Classico hills and woods and is the ideal place to spend a relaxing holiday in close contact with nature. A large 8000 square-meter garde  …see more

from £402 / night

£2813 - £4090 / week

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from £402 / night

1 / 100

Ester - Castellina In Chianti villa sleeps 12

Province of Siena / Castellina In Chianti

5 bedroomsSleeps 127 nights min stay

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Nearest beach 85 km; Swimming pool; Great for children of all ages ;
ExteriorsLocated in the heart of the Chianti region, this extraordinary villa boasts views over the hills, the valleys and the countryside at its fullest. It is situated very close to Castellina in Chianti, a town in the province of Siena with ancient constructions, an  …see more

from £335 / night

£2345 - £3401 / week

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from £335 / night

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Castellina - large - Castellina In Chianti apartment sleeps 6

Province of Siena / Castellina In Chianti

2 bedroomsSleeps 63 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Swimming pool; Great for children of all ages ; No pets allowed;
All the large apartments are located in Dario's House that is the oldest building of the Hamlet. This beautiful stone building that imposes its structure on the Valley was an old watch little fortified house. The building has been carefully restored and divided int  …see more

from £155 / night

£1080 - £1435 / week

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from £155 / night

1 / 100

Castellina - Torre - Castellina In Chianti apartment sleeps 6

Province of Siena / Castellina In Chianti

2 bedroomsSleeps 63 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Swimming pool; Great for children of all ages ; No pets allowed;
Torre is an old stone tower converted in a independent small villa. The accommodation has two nice double bedrooms and two bathrooms, a little studio, kitchen, sitting room, and a big living room with double sofa bed and working fireplace.This small villa in Tuscany is  …see more

from £180 / night

£1255 - £1616 / week

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from £180 / night

1 / 100

Castellina In Chianti 46441 - Castellina In Chianti villa sleeps 16

Province of Siena / Castellina In Chianti

8 bedroomsSleeps 167 nights min stay

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
Beautiful restored farmhouse with swimming-pool situated in the heart of the Chianti Classico area, a few kilometers away from Castellina in Chianti. This property is quietly situated on a large 220-hectare farming estate producing excellent wines. Tastefully furnished,  …see more

from £379 / night

£2648 - £3009 / week

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from £379 / night

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Villa Rosa - Castellina In Chianti villa sleeps 12

Province of Siena / Castellina In Chianti

6 bedroomsSleeps 127 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Nearest beach 120 km; Swimming pool; Great for children of all ages ;
Everything about this property is classically Tuscan. If you dream of typical Tuscany as breathtaking panoramas, misty hills covered in precision lines of vineyards, olive groves, gravel roads and driveways shadily lined with pointy cypress trees, and grand villas with  …see more

from £554 / night

£3875 / week

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from £554 / night

(2) Very Good 

1 / 20

LYRA apartment @ CASALTA DI PESA - Castellina In Chianti house sleeps 5

Province of Siena / Castellina In Chianti

4 bedroomsSleeps 5Min stay varies

  • 4 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 100 km; Swimming pool; Great for children of all ages ;
Beautiful stone Tuscan hamlet dating back to the 16th century and nestling deep among the splendid Chianti Classico vineyards. This property still shows the blazon of the astronomer Galileo Galilei who stayed in this hamlet many years and drew inspiration from the beau  …see more

from £102 / night

£675 - £1142 / week

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from £102 / night

1 / 13

La Tinaia - beautiful 1 bedroom cottage & garden

Province of Siena / Castellina In Chianti

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Not suitable for children; No pets allowed;
Podere Patrignone is a beautiful old 15th Century estate ('podere') which has been lovingly and tastefully restored. Patrignone is set on top of it's own hill reached by a long, winding private road that ends at Patrignone. It is set in 150 acres of fores  …see more

from £127 / night

£757 - £933 / week

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from £127 / night

1 / 16

Luxury Chianti apartment with shared pool, private garden, barbecue

Province of Siena / Castellina In Chianti

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
Come to the heart of the Chianti region to discover a wonderfully charming inn and agritourism facility that offers hotel-like amenities in elegant apartment suites, set in the evocative atmosphere of the Tuscan hills. Resting on a rolling hill, the Borgo is located  …see more

from £132 / night

£922 - £1552 / week

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from £132 / night

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Siena Chianti Farmhouse Flat - Castellina In Chianti apartment sleeps 8

Province of Siena / Castellina In Chianti

2 bedroomsSleeps 8Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Nearest beach 90 km; Great for children of all ages ; Car essential;
Immersed in the country but within walking distance of Castellina in Chianti, a 150 sq.m. apartment in an old stone, Chianti farmhouse with its own big, enclosed private garden. The rooms are all large, the ceilings are beamed and terracotta tiled, floors terracotta til  …see more

from £96 / night

£671 - £730 / week

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from £96 / night

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ANDROMEDA - CASALTA DI PESA - Castellina In Chianti villa sleeps 6

Province of Siena / Castellina In Chianti

4 bedroomsSleeps 6Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Great for children of all ages ; Some pets are welcome - please contact the owner; Private garden;
Beautiful stone Tuscan hamlet dating back to the 16th century comprising 8 accommodations and nestling deep among the splendid Chianti Classico vineyards. This property still shows the blazon of the astronomer Galileo Galilei who stayed in this hamlet many years and dre  …see more

from £117 / night

£680 - £1375 / week

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from £117 / night

1 / 13

Il Granaio - Castellina In Chianti house sleeps 6

Province of Siena / Castellina In Chianti

2 bedroomsSleeps 67 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car not necessary;
Luxury interior designed 2 bedroom house in stunning position in Chianti countryside with a private garden (half acre) and 2 terccaces. Shared swimming pool and tennis courts within a medieval village setting. 12km from Castellina in Chianti, 7km from Poggibonsi. Stunn  …see more

from £83 / night

£575 - £940 / week

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from £83 / night

(2) Excellent 

1 / 20

Casa del Fico - Castellina In Chianti farmhouse sleeps 6

Province of Siena / Castellina In Chianti

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
The house forms part of the oldest wing of Le Bagnaie, a 300 year old farm on a secluded hilltop, which was converted into 8 privately owned houses in 1990. All are beautifully restored in traditional rustic style, with exposed beams, old terracotta floors and open fir  …see more

from £165 / night

£1150 - £1950 / week

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from £165 / night

1 / 8

Il Torrino - Castellina In Chianti villa sleeps 7

Province of Siena / Castellina In Chianti

4 bedroomsSleeps 7Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
Inside, the property is set over 3 floors. On the ground floor, there is an open plan living and dining area, a separate well equipped kitchen, bathroom and 2 double bedrooms. A spiral staircase leads guests up the watchtower to a pretty single bedroom. Another spiral s  …see more

from £179 / night

£1250 - £2084 / week

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from £179 / night

1 / 16

Villa Fontana - Castellina In Chianti villa sleeps 8

Province of Siena / Castellina In Chianti

4 bedroomsSleeps 82 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
This beautiful, detached stone farmhouse, situated near Castellina in Chianti, was restored in 1995. Surrounded by ample private grounds, it sits in a panoramic position and is reached by its own driveway.The garden spaces and external paved terraces are all abundantly  …see more

from £526 / night

£2103 - £3756 / week

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from £526 / night

1 / 25

Province of Siena / Castellina In Chianti

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Ask owner if suitable for children; Some pets are welcome - please contact the owner; Private garden;
 …see more

from £68 / night

£471 - £589 / week

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from £68 / night

1 / 16

Province of Siena / Castellina In Chianti

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Pets welcome;
 …see more

from £194 / night

£1177 / week

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from £194 / night

1 / 15

Apartment 507 - Castellina In Chianti apartment sleeps 2

Province of Siena / Castellina In Chianti

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; No pets allowed;
Bed places : 2Two Rooms, 40 sqm, a kitchen and tv, a double bedroom, a bathroom with shower. The apartments are at the first floor. On the ground floor externally there are tables, chairs and umbrellas for common use. Can host one more child (max 12 years) with accommod  …see more

from £59 / night

£409 - £496 / week

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from £59 / night

(1) Excellent 

1 / 24

Villa Patrignone 7 bedroom Tuscany villa with pool

Province of Siena / Castellina In Chianti

7 bedroomsSleeps 14Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
Key info: Nearest beach 90 km; Swimming pool; Great for children of all ages ;
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  …see more

from £380 / night

£2280 - £3936 / week

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from £380 / night

(4) Very Good 

1 / 8

Province of Siena / Castellina In Chianti

2 bedroomsSleeps 57 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Pets welcome;
 …see more

from £110 / night

£757 - £1093 / week

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from £110 / night

1 / 14

Le Stalle, Podere Patrignone - Castellina In Chianti apartment sleeps 5

Province of Siena / Castellina In Chianti

2 bedroomsSleeps 55 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 5 nights min stay
Key info: Nearest beach 80 km; Swimming pool; Great for children of all ages ;
Rather unglamorously, this apartment used to house livestock owned by the tenant farmers. However, the transformation could not be more complete. Two large beautiful arched windows are the main feature of this bright 2-bedroom apartment.A covered entrance leads to a ver  …see more

from £180 / night

£1075 - £1388 / week

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from £180 / night

1 / 18

FORNO AGRITURISMO IL CELLESE - Castellina In Chianti farmhouse sleeps 3

Province of Siena / Castellina In Chianti

1 bedroomSleeps 3Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
Key info: Nearest beach 120 km; Swimming pool; Great for children of all ages ;
Located between Florence and Siena, its undulating hills evoke the refined country life of antiquity while maintaining its beauty and balance. Along its extensive terrain, oak forests alternate with cypress, vineyards and centennial olive trees. Here, the best Tuscan w  …see more

Pricing unknown

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1 / 100

Castellina In Chianti 44148 - Castellina In Chianti villa sleeps 6

Province of Siena / Castellina In Chianti

2 bedroomsSleeps 67 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
Beautiful independent villa with swimming-pool situated near Castellina in Chianti, in the heart of the Chianti Classico area. This property was recovered by restoring the outbuilding of an ancient manor house. The restoration was very accurate and aimed to preserve the  …see more

from £155 / night

£1083 - £1324 / week

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from £155 / night

1 / 23

FIENILE AGRITURISMO IL CELLESE - Castellina In Chianti farmhouse sleeps 5

Province of Siena / Castellina In Chianti

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 120 km; Swimming pool; Great for children of all ages ;
Located between Florence and Siena, its undulating hills evoke the refined country life of antiquity while maintaining its beauty and balance. Along its extensive terrain, oak forests alternate with cypress, vineyards and centennial olive trees. Here, the best Tuscan w  …see more

Pricing unknown

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Pricing unknown

1 / 13

CISPIANO AGRITURISM IL CELLESE - Castellina In Chianti farmhouse sleeps 6

Province of Siena / Castellina In Chianti

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 120 km; Swimming pool; Great for children of all ages ;
Located between Florence and Siena, its undulating hills evoke the refined country life of antiquity while maintaining its beauty and balance. Along its extensive terrain, oak forests alternate with cypress, vineyards and centennial olive trees. Here, the best Tuscan w  …see more

from £125 / night

£500 - £1250 / week

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from £125 / night

1 / 14

LOFT AGRITURISMO IL CELLESE - Castellina In Chianti farmhouse sleeps 4

Province of Siena / Castellina In Chianti

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 120 km; Swimming pool; Great for children of all ages ;
Located between Florence and Siena, its undulating hills evoke the refined country life of antiquity while maintaining its beauty and balance. Along its extensive terrain, oak forests alternate with cypress, vineyards and centennial olive trees. Here, the best Tuscan w  …see more

Pricing unknown

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Pricing unknown

1 / 16

Province of Siena / Castellina In Chianti

9 bedroomsSleeps 16Min stay varies

  • 9 bedrooms
  • Sleeps 16
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £417 / night

£2917 / week

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from £417 / night

1 / 14

NICCHIE AGRITURISMO IL CELLESE - Castellina In Chianti farmhouse sleeps 7

Province of Siena / Castellina In Chianti

2 bedroomsSleeps 7Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
Key info: Nearest beach 120 km; Swimming pool; Great for children of all ages ;
Located between Florence and Siena, its undulating hills evoke the refined country life of antiquity while maintaining its beauty and balance. Along its extensive terrain, oak forests alternate with cypress, vineyards and centennial olive trees. Here, the best Tuscan w  …see more

Pricing unknown

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Pricing unknown

(2) Excellent 

1 / 24

Province of Siena / Castellina In Chianti

3 bedroomsSleeps 77 nights min stay

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min stay
Key info: Nearest beach 85 km; Swimming pool; Great for children of all ages ;
 …see more

from £191 / night

£1336 / week

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from £191 / night

1 / 10

15462-Apartment Chianti - Castellina In Chianti apartment sleeps 5

Province of Siena / Castellina In Chianti

3 bedroomsSleeps 57 nights min stay

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car not necessary;
Three Bedroom Ground Floor Apartment Chianti<br><br>Castellina is a charming apartment, part of a farmhouse situated in beautiful Chianti countryside. The apartment opens onto its own lovely shaded terrace with table and chairs for dining al fresco, and ther  …see more

from £56 / night

£391 - £803 / week

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from £56 / night

1 / 22

46441001 - Castellina In Chian - Castellina In Chianti farmhouse sleeps 16

Province of Siena / Castellina In Chianti

8 bedroomsSleeps 167 nights min stay

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Some pets are welcome - please contact the owner;
Beautiful restored farmhouse with swimming-pool situated in the heart of the Chianti Classico area, a few kilometers away from Castellina in Chianti. This property is quietly situated on a large 220-hectare farming estate producing excellent wines. Tastefully furnished,  …see more

from £379 / night

£2648 - £3610 / week

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from £379 / night

1 / 14

Province of Siena / Castellina In Chianti

3 bedroomsSleeps 7Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
Key info: Great for children of all ages ; No pets allowed;
 …see more

from £41 / night

£269 - £630 / week

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from £41 / night

1 / 18

59736001 - Castellina In Chian - Castellina In Chianti farmhouse sleeps 4

Province of Siena / Castellina In Chianti

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Some pets are welcome - please contact the owner;
Beautiful stone Tuscan hamlet dating back to the 16th century comprising 8 accommodations and nestling deep among the splendid Chianti Classico vineyards. This property still shows the blazon of the astronomer Galileo Galilei who stayed in this hamlet many years and dre  …see more

from £111 / night

£654 - £1098 / week

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from £111 / night

(2) Excellent 

1 / 17

Province of Siena / Castellina In Chianti

1 bedroomSleeps 47 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Ask owner if suitable for children; Car advised;
 …see more

from £37 / night

£253 / week

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from £37 / night

Top Destination reviews

Farm holidays in Chianti
A Christams dream

This year my husband and I decided to spend Christmas on our own, in the Chianti countryside. La Capanna delle Cozzole is just the perfect location: very quiet, romantic and private location. In the village you can find top quality food, wine and d … see more

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