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

Close

Castellina In Chianti

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this vacation rental you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

135 Vacation rentals

15

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

from $60 / night

$415 / week

Book View

from $60 / night

(5) Excellent 

48

Province of Siena / Castellina In Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 150 mi
  • Child friendly
  • Private garden

from $131 / night

$608 - $727 / week

Book View

from $131 / night

24

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

from $76 / night

$528 / week

Book View

from $76 / 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 $70 / night

$489 - $814 / week

Inquire View

from $70 / night

(2) Excellent 

24

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 $125 / night

$950 / week

Book View

from $125 / night

(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 $495 / night

$2967 - $5124 / week

Book View

from $495 / night

21

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 $144 / night

$843 - $1414 / week

Inquire View

from $144 / night

24

Vacation farmhouse with swimming pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Ask about pets
  • Private garden
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 …see more

from $617 / night

$4318 - $7583 / week

Inquire View

from $617 / night

21

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 $144 / night

$843 - $1414 / week

Inquire View

from $144 / 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

from $248 / night

$1506 / week

Book View

from $248 / 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

from $86 / night

$597 - $1782 / week

Book View

from $86 / night

22

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 $144 / night

$843 - $1414 / week

Inquire View

from $144 / 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 $83 / night

$485 - $807 / week

Inquire View

from $83 / night

22

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 $188 / night

$1097 - $1926 / week

Inquire View

from $188 / 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 $719 / night

$2870 - $4411 / week

Inquire View

from $719 / night

20

Vacation villa with swimming pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
This beautiful independent villa has a private pool and is located in a scenic position, upon the Chianti Classico hills. This rental is surrounded by olive groves, vineyards and woods and the products of the estate (wine and olive oil) are available for clients to be p …see more

from $397 / night

$2776 - $5215 / week

Inquire View

from $397 / 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

Pricing unknown

Book View

Pricing unknown

(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

from $47 / night

$326 - $489 / week

Book View

from $47 / night

14

Province of Siena / Castellina In Chianti

3 7 2 nights min

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

from $53 / night

$347 - $612 / week

Book View

from $53 / 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

from $388 / night

$1627 - $4317 / week

Book View

from $388 / 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 $80 / night

$554 - $923 / week

Inquire View

from $80 / night

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

from $136 / night

$950 / week

Book View

from $136 / 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 +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 $178 / night

$1243 - $1469 / week

Book View

from $178 / 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 $234 / night

$1632 - $2752 / week

Book View

from $234 / 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 $76 / night

$528 - $640 / week

Book View

from $76 / night

17

Farmhouse rental in Castellina In Chianti with shared pool

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
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 $98 / night

$685 - $1194 / week

Inquire View

from $98 / night

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 $161 / night

$1891 / week

Inquire View

from $161 / 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 $721 / night

$5045 / week

Inquire View

from $721 / night

17

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 $114 / night

$798 - $950 / week

Book View

from $114 / night

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 forest, olives and v …see more

from $163 / night

$977 / week

Book View

from $163 / 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

Book View

Pricing unknown

(1) Very Good 

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 $225 / night

$1573 - $2929 / week

Book View

from $225 / 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

Book View

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

Book View

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

Book View

Pricing unknown

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 $232 / night

$1388 - $1501 / week

Book View

from $232 / 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 $76 / night

$528 - $640 / week

Book View

from $76 / night

18

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 $76 / night

$532 - $646 / week

Book View

from $76 / 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

Book View

Pricing unknown

26

Vacation home in Castellina In Chianti

Province of Siena / Castellina In Chianti

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Child friendly
  • Pet friendly
Just between Florence and Siena there is the Chianti Classico. Its enchanting towns and medieval villages like Castellina in Chianti and Panzano in Chianti are surrounded by a sea of vines and olives whose slopes intermittently give way to deep forest of pines, chestnut …see more

from $323 / night

$2259 - $3227 / week

Book View

from $323 / night

1