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

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Castellina In Chianti

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6,338 Vacation rentals

44

Vacation villa with swimming pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

6 13 1 night min

  • 6 bedrooms
  • Sleeps 13
  • 1 night min
  • Nearest beach 110 mi
  • Swimming pool
  • Child friendly
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 landsc …see more

from $684 / night

$4,790 - $7,307 / week

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from $684 / night

25

Apartment rental in Castellina In Chianti

Province of Siena / Castellina In Chianti

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Nearest beach 90 mi
  • Child friendly
  • Private garden
Lovely apartment of 40 square meters. Carefully renovated according to the ancient Tuscan traditions. This is one of the two apartments which make up the old barn. Nestled in the heart of Chianti Classico, well studied in details, comfortable and suitable for singles …see more

from $68 / night

$473 / week

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from $68 / night

14

Apartment rental in Castellina In Chianti

Province of Siena / Castellina In Chianti

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Child friendly
Confortevole e moderna mansarda tra le incantevoli colline del Chianti. Al 1° piano si trovano una cucina spaziosa , il soggiorno ed un piccolo bagno provvisto di lavatrice. Al 2° piano, mansardato, si trovano le tre camere da letto , tutte arredate con mobili modern …see more

from $97 / night

$613 - $914 / week

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from $97 / night

46

Vacation apartment in Castellina In Chianti

Province of Siena / Castellina In Chianti

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Nearest beach 85 mi
  • Child friendly
  • Private garden
Lovely apartment of 85 square meters. Carefully renovated according to the ancient Tuscan traditions. This is one of the two apartments which make up the old barn. Nestled in the heart of Chianti Classico, well studied in details, comfortable and suitable for singles, …see more

from $86 / night

$602 / week

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from $86 / night

(6) Excellent 

Certificate of Excellence

48

Vacation cottage in Castellina In Chianti

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
Traditional, independent house in peaceful countryside in the heart of Chianti La Capanna delle Cozzole is located close to Castellina in Chianti, only a 30 minute drive from Siena, Florence and San Gimignano. It is set perfectly in the lush countryside between ancient …see more

Certificate of Excellence

from $148 / night

$688 - $811 / week

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Responds fast!
avg. 3 hours 17 minutes

from $148 / night

(5) Very Good 

29

Castellina In Chianti Vacation villa rental

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
Our villa located within walking distance from Tregole in the famous wine region of Chianti Classico, has five spacious bedrooms and three bathrooms. The villa is centrally located between vineyards, olive groves and woods that make staying in an area of ​​tranquility, …see more

from $490 / night

$1,596 - $5,055 / week

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Responds fast!
avg. 3 hours 13 minutes

from $490 / night

(3) Very Good 

24

Vacation villa rental

Province of Siena / Castellina In Chianti

3 7 5 nights min

  • 3 bedrooms
  • Sleeps 7
  • 5 nights min
  • Nearest beach 85 mi
  • Swimming pool
  • Child friendly
Cypressess Villa is a unique house, a spacious stone made house surrounded by green and peaceful land, ideal for those who like outdoor activities but suitable for those who like to stay home and cook his meal made with fresh products available in the neighborhood or en …see more

from $332 / night

$2,088 / week

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Responds fast!
avg. 1 hour 45 minutes

from $332 / night

(2) 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 $560 / night

$3,359 - $5,801 / week

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from $560 / night

13

Castellina In Chianti Vacation barn rental

Province of Siena / Castellina In Chianti

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Private garden
Our apartment is' ideal for a relaxing holiday in Chianti. The apartment and 'a portion of a typical Tuscan barn, bright, surrounded by vineyards, olive trees and all around the wood, with a lovely terrace from which you can' appreciate all the facets of the Tuscan coun …see more

from $86 / night

$553 / week

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from $86 / night

(2) Excellent 

16

Castellina In Chianti Vacation apartment rental

Province of Siena / Castellina In Chianti

2 8 3 nights min

  • 2 bedrooms
  • Sleeps 8
  • 3 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 $154 / night

$1,075 / week

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from $154 / night

17

Vacation apartment with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
The apartment is located within a typical Tuscan farmhouse in the small village of Tregole, about 5 km from Castellina in Chianti. Nestled in the beautiful hills of the Chianti area for a relaxing holiday by the pool or as a starting point for day trips to Siena, San Gi …see more

from $96 / night

$671 / week

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from $96 / night

(1) Very Good 

12

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 +1 Four 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 $203 / night

$1,677 / week

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from $203 / night

16

Vacation villa in Castellina In Chianti

Province of Siena / Castellina In Chianti

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
I enrolled in January 2016. It is an ancient villa in Chianti between Siena and Florence stone on two floors. Entrance hall, large living room, dining room, kitchen, two bathrooms, three bedrooms (7 beds). Antique Tuscan style décor. Large three-storey garden with barbe …see more

from $246 / night

$1,535 / week

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Responds fast!
avg. 2 hours 27 minutes

from $246 / night

(2) Very Good 

20

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’ mo …see more

from $79 / night

$553 - $921 / week

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from $79 / night

(4) Very Good 

32

Vacation apartment with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Located in the heart of Chianti, just 8 Km from the castle of Monteriggioni and at 4 Km from Castellina in Chianti is Chianti suite Quornia Village, finely arredanto apartment, nestled in the charming villa of Quornia Village, ancient rural village made entirely of ston …see more

from $85 / night

$602 - $1,771 / week

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from $85 / 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 to a v …see more

from $264 / night

$1,585 - $2,131 / week

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from $264 / night

13

Vacation cottage with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • 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 its own hill reached by a long, winding private road that ends at Patrignone. It is set in 150 acres of forest, olives and vi …see more

from $185 / night

$1,124 - $1,364 / week

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from $185 / night

30

Vacation apartment with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
In the prestigious area of Chianti, the most visited in Tuscany, you will find this charmimg 80 m2 appartment in a lovely hamlet with all the conforts you need in order to truly enjoy your holidays and relax in our swimming pool and tennis court with stunning views. T …see more

from $182 / night

$980 - $1,820 / week

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from $182 / 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 $255 / night

$1,785 / week

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from $255 / night

(1) Very Good 

8

Vacation villa with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

4 7 2 nights min

  • 4 bedrooms
  • Sleeps 7
  • 2 nights min
  • 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 $255 / night

$1,781 - $3,316 / week

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Responds fast!
avg. 3 hours 15 minutes

from $255 / night

9

Vacation farmhouse rental

Province of Siena / Castellina In Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • 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

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

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

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

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

17

Farmhouse 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 apartment in an ancient hamlet of houses nestling deep amidst the Chianti Classico hills, within the Sant’Agnese natural preserve. This hamlet, offering beautiful views over the surrounding landscape, has been recently restored preserving its original architec …see more

from $110 / night

$775 - $1,351 / week

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from $110 / night

12

Vacation b&b with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
A renovated former farm, rooms for 2 persons with separate entrance, each with bathroom and air conditioned, equipped with every comfort. Coffee facilities. Courtesy set Presence of the owners in the outdoor pool with sun loungers. Breakfast buffet with homemade product …see more

from $111 / night

$774 / week

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from $111 / night

14

Vacation apartment with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 90 mi
  • Swimming pool
Come and soak up poolside serenity in the country; and discover a local treasure trove of Tuscan cities! Situated in a farmhouse in the beautiful Tuscan countryside, this mezzanine apartment provides a great base from which to relax and explore the nearby famous cities …see more

from $85 / night

$590 - $823 / week

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from $85 / 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

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

10

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
Bed places : 4 Three rooms, 60 square meters, with kitchen and TV, 2 double bedrooms (one with high window), a bathroom with shower. The apartment is at the first floor. On the ground floor there are tables, chairs and umbrellas for common use outdoors. It is pos …see more

from $129 / night

$1,075 / week

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from $129 / night

16

Vacation condo with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

9 16 Min stay varies

  • 9 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
With a little imagination we have converted the old Cottage in a beautiful home and a wonderful convent Millennium apartments used to farm. The hut, which is divided into two apartments, is situated at the top of the hill from which opens a rich landscape of vineyards, …see more

Pricing unknown

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Pricing unknown

18

Apartment rental in Castellina In Chianti with shared pool

Province of Siena / Castellina In Chianti

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
In the heart of Chianti, a former farmhouse restored with every comfort. The structure is divided into rooms and apartments with kitchen, all with private entrance. It is a short distance from Siena, San Gimignano, Florence. Outdoor swimming pool, air conditioning, heat …see more

from $234 / night

$1,634 / week

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from $234 / night

20

Vacation farmhouse with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
This is an impressive complex made up of nine apartments located on a beautiful hill within the famous Chianti Classico zone. The two “Marinella” apartments are positioned near the swimming pool and each has its own private and furnished outdoor area. The two apartmen …see more

from $79 / night

$553 - $921 / week

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from $79 / night

20

Vacation farmhouse with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
This is an impressive complex made up of nine apartments located on a beautiful hill within the famous Chianti Classico zone. The two “Marinella” apartments are positioned near the swimming pool and each has its own private and furnished outdoor area. The two apartmen …see more

from $90 / night

$627 - $1,044 / week

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from $90 / night

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 : 2 Two 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 $86 / night

$731 / week

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from $86 / night

11

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
Bed places : 4 Three rooms, 55 sqm, consisting of small kitchen and TV, 2 double bedrooms, a bathroom with shower. The apartment is at the first floor. On the ground floor there are tables, chairs and umbrellas for common use. Prices include: Bed and bathro …see more

from $129 / night

$1,075 / week

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from $129 / night

11

Vacation apartment with shared pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
Bed places: 3 Two rooms, 42 sqm, kitchen with wall bed (to be open in the evening and close in the morning), TV, a double bedroom, 2 bathrooms with shower. On the ground floor front with table, chairs and umbrella. Prices include: Bed and bathroom linen and …see more

from $111 / night

$946 / week

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from $111 / night

23

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 : 2 Two 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 $93 / night

$774 / week

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from $93 / night

9

Apartment rental in Castellina In Chianti with shared pool

Province of Siena / Castellina In Chianti

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
Bed places : 2+2 60 square meters, consisting of kitchen, living room with sofa bed and foldaway bed, TV, a double bedroom, a bathroom with shower. On the ground floor front with table, chairs and umbrella. It is possible to accommodate a + child (max 12 years) w …see more

from $129 / night

$1,075 / week

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from $129 / night