50 Best Vacation Rentals in Castellina In Chianti - Holiday Lettings - Cabins

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Castellina In Chianti

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153 Vacation rentals

20

Province of Siena / Castellina In Chianti

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly

 …see more

from $134 / night

$934 / week

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from $134 / night

(2)  

30

Province of Siena / Castellina In Chianti

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden

 …see more

from $149 / night

$586 - $885 / week

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from $149 / night

(5) Excellent 

48

Province of Siena / Castellina In Chianti

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Nearest beach 150 mi
  • Child friendly
  • Private garden

 …see more

from $129 / night

$609 - $726 / week

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from $129 / night

8

Vacation villa with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
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 $222 / night

$1548 - $2882 / week

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from $222 / night

24

Vacation villa rental

Province of Siena / Castellina In Chianti

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 120 mi
  • Swimming pool
  • Child friendly
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 $709 / night

$4963 / week

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from $709 / night

(2) Very Good 

100

Castellina In Chianti Vacation villa rental

Province of Siena / Castellina In Chianti

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • 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 $421 / night

$2454 - $3675 / week

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from $421 / night

100

Vacation villa with swimming pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

5 8 7 nights min

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • 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 $517 / night

$3613 - $5253 / week

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from $517 / night

(2) Excellent 

22

Province of Siena / Castellina In Chianti

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly

 …see more

from $46 / night

$321 - $481 / week

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from $46 / night

24

Vacation farmhouse with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 120 mi
  • Swimming pool
  • Child friendly
Sergio is a two storey ground floor apartment at the one end of the main building. It has a private furnished terrace that overlooks the olive groves, vineyards ande the picturesque countryside.Entry is directly into the main living room, complete with a wood burnin  …see more

Pricing unknown

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Pricing unknown

(1) Excellent 

24

Villa rental in Castellina In Chianti with shared pool

Province of Siena / Castellina In Chianti

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
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 $487 / night

$2919 - $5041 / week

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from $487 / night

16

Province of Siena / Castellina In Chianti

9 16 Min stay varies

  • 9 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

Pricing unknown

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Pricing unknown

16

Vacation castle with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
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 $169 / night

$1181 - $1637 / week

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from $169 / night

16

Castellina In Chianti Vacation villa rental

Province of Siena / Castellina In Chianti

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
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 abu  …see more

from $675 / night

$2698 - $4409 / week

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from $675 / night

(1) Very Good 

24

Vacation apartment with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
Bed places: 6 +1Four rooms, 90 sqm, fully equipped kitchen and living room, 3 double bedrooms (one with high window). Inside, each bedroom has TV and bathroom with shower (total 3 baths). On the ground floor with a private terrace with tables, chairs and umbrellas.  …see more

from $177 / night

$1233 - $1457 / week

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from $177 / night

13

Vacation farmhouse in Castellina In Chianti

Province of Siena / Castellina In Chianti

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 120 mi
  • Swimming pool
  • Child friendly
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

23

Vacation farmhouse rental

Province of Siena / Castellina In Chianti

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 120 mi
  • Swimming pool
  • Child friendly
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

13

Vacation cottage with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Private garden
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 $161 / night

$961 / week

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from $161 / night

14

Province of Siena / Castellina In Chianti

3 7 2 nights min

  • 3 bedrooms
  • Sleeps 7
  • 2 nights min
  • Child friendly

 …see more

from $52 / night

$341 - $602 / week

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from $52 / night

100

Vacation villa with swimming pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

8 16 7 nights min

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • 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 $485 / night

$3391 - $3401 / week

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from $485 / night

14

Vacation farmhouse rental

Province of Siena / Castellina In Chianti

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 120 mi
  • Swimming pool
  • Child friendly
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

(3) Very Good 

24

Province of Siena / Castellina In Chianti

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Nearest beach 85 mi
  • Swimming pool
  • Child friendly

 …see more

from $245 / night

$1711 / week

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from $245 / night

13

Home rental in Castellina In Chianti with shared pool

Province of Siena / Castellina In Chianti

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • 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 $105 / night

$731 / week

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from $105 / night

18

Vacation farmhouse in Castellina In Chianti

Province of Siena / Castellina In Chianti

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 120 mi
  • Swimming pool
  • Child friendly
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

100

Vacation apartment with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
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 $122 / night

$852 - $1412 / week

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from $122 / night

(2) Excellent 

20

Vacation farmhouse in Castellina In Chianti

Province of Siena / Castellina In Chianti

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
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 $232 / night

$1620 - $2731 / week

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from $232 / night

14

Castellina In Chianti Vacation apartment rental

Province of Siena / Castellina In Chianti

2 5 5 nights min

  • 2 bedrooms
  • Sleeps 5
  • 5 nights min
  • Nearest beach 80 mi
  • Swimming pool
  • Child friendly
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  …see more

from $230 / night

$1377 - $1489 / week

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from $230 / night

16

Province of Siena / Castellina In Chianti

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from $246 / night

$1495 / week

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from $246 / night

18

Castellina In Chianti Vacation farmhouse rental

Province of Siena / Castellina In Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
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 $140 / night

$830 - $1391 / week

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from $140 / night

14

Vacation farmhouse rental

Province of Siena / Castellina In Chianti

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 120 mi
  • Swimming pool
  • Child friendly
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

15

Apartment rental in Castellina In Chianti with shared pool

Province of Siena / Castellina In Chianti

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
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 acco  …see more

from $75 / night

$523 - $635 / week

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from $75 / night

(3) Excellent 

24

Castellina In Chianti Vacation apartment rental

Province of Siena / Castellina In Chianti

2 8 4 nights min

  • 2 bedrooms
  • Sleeps 8
  • 4 nights min
  • Nearest beach 90 mi
  • Child friendly
  • Private garden
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 $134 / night

$934 / week

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from $134 / night

17

Castellina In Chianti Vacation farmhouse rental

Province of Siena / Castellina In Chianti

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
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 $140 / night

$830 - $1391 / week

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from $140 / night

18

Castellina In Chianti Vacation farmhouse rental

Province of Siena / Castellina In Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
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 $140 / night

$830 - $1391 / week

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from $140 / night

100

Vacation apartment with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
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 into apa  …see more

from $198 / night

$1383 - $2279 / week

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from $198 / night

100

Vacation villa with swimming pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 85 mi
  • Swimming pool
  • Child friendly
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

Pricing unknown

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Pricing unknown

100

Vacation apartment with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
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 $230 / night

$1607 - $2742 / week

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from $230 / night

(2) Very Good 

23

Apartment rental in Castellina In Chianti with shared pool

Province of Siena / Castellina In Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Welcoming accommodation situated in a small hamlet of 7 houses on the Chianti Classico hills. This apartment is on the second floor of an ancient farmhouse and it is in convenient location for visiting the Chianti region with its charming villages as well as Tuscany’  …see more

from $83 / night

$481 - $801 / week

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from $83 / night

100

Vacation apartment with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Swimming pool
  • Child friendly
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 $130 / night

$904 - $1487 / week

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from $130 / night

36

Province of Siena / Castellina In Chianti

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Pet friendly

 …see more

from $138 / night

$961 - $1388 / week

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from $138 / night

(4) Very Good 

28

Province of Siena / Castellina In Chianti

5 15 Min stay varies

  • 5 bedrooms
  • Sleeps 15
  • Min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly

 …see more

from $230 / night

$1600 - $4770 / week

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from $230 / night