List your home
Apply filters
£ to

43 Holiday homes in Castellina in Chianti

Reset search

Show results on map

Also consider

Coastal Cottages
222 properties
Sardinia
478 properties
Tuscany
3,181 properties
Lake Garda Area
103 properties
Lake Como Area
494 properties
Sicily
634 properties
Rome
2,495 properties
Florence
983 properties
Venice, Veneto
498 properties
Trapani
482 properties
Amalfi Coast
452 properties
Lucca
439 properties
Palermo
412 properties
Cortona
411 properties
Sorrento, Campania
351 properties
Cefalu
315 properties
San Gimignano
289 properties
Taormina
276 properties
Greve in Chianti
262 properties
Massa Lubrense
245 properties

Filters applied: Pets allowed (43)

To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more
43 Results  |  
24 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

Add to shortlist

from £536 /night

£3750 / week

View

Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Just 4 km from Castellina in Chianti Villa Rosa boasts unique views over the Chianti countryside from its romantic terrace and from whole of the villa. The classically furnished interior complete the picture.  …see more

24 Photos

Farmhouse | 2 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £74 /night

£513 - £1496 / week

View

Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Pets welcome
www.ilcellese.it  …see more

13 Photos

Farmhouse | 2 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £74 /night

£513 - £1026 / week

View

Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
CHIANTI , TOSCANA , AGRITURISMO , WINE , COOKING CLASS , LANDSCAPE , VIEW , SWIMMING POOL  …see more

Featured properties

12 Photos

Farmhouse | 3 Bedrooms | sleeps 6

4 Nights min stay

Add to shortlist

from £90 /night

£627 - £1052 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Castellina In Chianti with 3 bedrooms sleeps 6  …see more

19 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

Add to shortlist

from £85 /night

£589 - £759 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Castellina In Chianti with 1 bedrooms sleeps 2  …see more

9 Photos

House | 3 Bedrooms | sleeps 7

7 Nights min stay

Add to shortlist

from £12 /night

£81 - £1355 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
This typical country house is located in the heart of Chianti Classico, near the famous town of Castellina.  …see more

12 Photos

Farmhouse | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £73 /night

£510 - £888 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Castellina In Chianti with 2 bedrooms sleeps 4  …see more

20 Photos

House | 3 Bedrooms | sleeps 6

1 night min stay

Add to shortlist

from £182 /night

£1270 - £1670 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Villa Arnica A is a characteristic and welcoming ancient tuscan country house surrounded by vineyards and olive groves. It sleeps six people. From Villa Arnica A you will enjoy a charming view of the Chianti hills  …see more

10 Photos

Apartment | 3 Bedrooms | sleeps 5

7 Nights min stay

Add to shortlist

from £56 /night

£389 - £600 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Apartment for 5 persons, with swimming pool , in Chianti  …see more

12 Photos

Farmhouse | 5 Bedrooms | sleeps 10

3 Nights min stay

Add to shortlist

from £262 /night

£1831 - £2742 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Castellina In Chianti with 5 bedrooms sleeps 10  …see more

11 Photos

Farmhouse | 2 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £156 /night

£1089 - £1331 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Castellina In Chianti with 2 bedrooms sleeps 6  …see more

12 Photos

Farmhouse | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £117 /night

£816 - £1433 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Castellina In Chianti with 2 bedrooms sleeps 4  …see more

12 Photos

Farmhouse | 2 Bedrooms | sleeps 4

4 Nights min stay

Add to shortlist

from £90 /night

£627 - £1052 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Castellina In Chianti with 2 bedrooms sleeps 4  …see more

12 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

Add to shortlist

from £74 /night

£513 - £589 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Castellina In Chianti with 1 bedrooms sleeps 2  …see more

12 Photos

Farmhouse | 3 Bedrooms | sleeps 5

3 Nights min stay

Add to shortlist

from £122 /night

£851 - £984 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Castellina In Chianti with 3 bedrooms sleeps 5  …see more

20 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

Add to shortlist

from £93 /night

£648 - £763 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Castellina In Chianti with 2 bedrooms sleeps 4  …see more

20 Photos

Villa | 7 Bedrooms | sleeps 14

2 Nights min stay

Add to shortlist

from £294 /night

£2055 - £3833 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
Villa Solara is a beautiful, modern villa, offering spectacular views of the surrounding countryside. Set within well-kept, private grounds and with easy access to local amenities, the villa is a perfect place for family or cultural holidays.  …see more

12 Photos

Farmhouse | 4 Bedrooms | sleeps 8

3 Nights min stay

Add to shortlist

from £139 /night

£968 - £1113 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Castellina In Chianti with 4 bedrooms sleeps 8  …see more

11 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

Add to shortlist

from £59 /night

£412 - £509 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Castellina In Chianti with 1 bedrooms sleeps 2  …see more

12 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

Add to shortlist

from £70 /night

£488 - £597 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Castellina In Chianti with 1 bedrooms sleeps 2  …see more

16 Photos

Villa | 6 Bedrooms | sleeps 11

2 Nights min stay

Add to shortlist

from £431 /night

£3014 - £4749 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
Food and wine-lovers wanting a memorable holiday in Tuscany shouldn't look any further than Villa Fermini. This beautiful farmhouse lies at the centre of an agricultural estate that produces excellent Chianti Classico wines and extra virgin olive oil.  …see more

12 Photos

Farmhouse | 2 Bedrooms | sleeps 4

4 Nights min stay

Add to shortlist

from £90 /night

£627 - £1052 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Castellina In Chianti with 2 bedrooms sleeps 4  …see more

12 Photos

Farmhouse | 6 Bedrooms | sleeps 13

7 Nights min stay

Add to shortlist

from £505 /night

£3529 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Castellina In Chianti with 6 bedrooms sleeps 13  …see more

12 Photos

Farmhouse | 5 Bedrooms | sleeps 8

7 Nights min stay

Add to shortlist

from £428 /night

£2995 - £4355 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Castellina In Chianti with 5 bedrooms sleeps 8  …see more

23 Photos

Farmhouse | 1 Bedroom | sleeps 4

3 Nights min stay

Add to shortlist

from £112 /night

£783 - £968 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Castellina In Chianti with 1 bedrooms sleeps 4  …see more

24 Photos

Cottage | 2 Bedrooms | sleeps 4

5 Nights min stay

Add to shortlist

from £102 /night

£709 - £1084 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • Pets welcome
Cottage Rosemaryandnbsp;is a picturesque stone cottage in the magnificent Chianti hills and valleys. Surrounded by magnificent vineyards and silvery olive groves, the cottage expands on one level and can accommodate up toandnbsp;five peopleandnbsp;in its lovely  …see more

16 Photos

Villa | 4 Bedrooms | sleeps 8

2 Nights min stay

Add to shortlist

from £255 /night

£1779 - £3242 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
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  …see more

24 Photos

Farmhouse | 3 Bedrooms | sleeps 6

5 Nights min stay

Add to shortlist

from £148 /night

£1035 - £1362 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • Pets welcome
Offering accommodations in a gorgeous ancient building formerly used as a monastery, this beautiful Tuscan villa features aandnbsp;large dining room, a fireplace, and simple kitchen.andnbsp; It can accommodate up toandnbsp;8 peopleandnbsp;with itsandnbsp;four bedrooms  …see more

12 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

Add to shortlist

from £111 /night

£771 - £888 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Castellina In Chianti with 2 bedrooms sleeps 4  …see more

12 Photos

Apartment | 2 Bedrooms | sleeps 4

Very Good 4.5/5 

3 Nights min stay

Add to shortlist

from £52 /night

£363 - £605 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Apartment / Condo in Castellina In Chianti with 2 bedrooms sleeps 4  …see more

12 Photos

Farmhouse | 6 Bedrooms | sleeps 12

7 Nights min stay

Add to shortlist

from £459 /night

£3210 - £5638 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Monteriggioni with 6 bedrooms sleeps 12  …see more

12 Photos

Farmhouse | 1 Bedroom | sleeps 2

3 Nights min stay

Add to shortlist

from £67 /night

£468 - £585 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Castellina In Chianti with 1 bedrooms sleeps 2  …see more

11 Photos

Apartment | 1 Bedroom | sleeps 6

7 Nights min stay

Add to shortlist

from £63 /night

£435 - £666 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Apartment for 6 persons, with swimming pool , in Chianti  …see more

20 Photos

House | 2 Bedrooms | sleeps 4

1 night min stay

Add to shortlist

from £125 /night

£870 - £1330 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Villa Arnica B is a graceful cottage surrounded by vineyards and olive groves. It sleeps four people. From Villa Arnica B you will enjoy a thrilling view of the Chianti hills and of the vineyards. Villa Arnica B is 100 square meters (1076 square feet)  …see more

12 Photos

Farmhouse | 8 Bedrooms | sleeps 16

7 Nights min stay

Add to shortlist

from £381 /night

£2662 - £2904 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Castellina In Chianti with 8 bedrooms sleeps 16  …see more

24 Photos

Cottage | 2 Bedrooms | sleeps 4

4 Nights min stay

Add to shortlist

from £68 /night

£471 - £556 / week

View

Key info:

  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
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 woods, olive trees and enchanting hills. Pets by arrangement. Not included: county tax 1,5 euro per person per day (up to seven days)  …see more

15 Photos

Apartment | 2 Bedrooms | sleeps 3

Min stay varies

Add to shortlist

Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
We are in the nature close to a river but at the same time near the village where you will find supermarket, shops and restaurants. In 20 mins walking distance you can also reach a public swimming pool of the village. Large garden all around and a spacius terrace with parasol, sunbeds sun chairs and table Free car parking!  …see more

14 Photos

Farmhouse | 2 Bedrooms | sleeps 7

Min stay varies

Add to shortlist

from £98 /night

£684 - £1197 / week

View

Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
WINE , CHIANTI , DOCG, VIEW , LANDSCAPE , AGRITURISMO  …see more

16 Photos

Condo | 9 Bedrooms | sleeps 16

Min stay varies

Add to shortlist

from £428 /night

£2992 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Pets welcome
  • Private garden
Arrivo: Sabato pomeriggio dalle 5 p.m. alle 8 p.m., Partenza: Sabato mattina entro le ore 10 a.m. * Esiste la possibilità di unire i due appartamenti * In dotazione: Tv Satellitare, riscaldamento autonomo, biancheria e cucina completamente attrezzata. * Aria condizi  …see more

14 Photos

Farmhouse | 1 Bedroom | sleeps 4

Min stay varies

Add to shortlist

from £74 /night

£513 - £984 / week

View

Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
WINE , CHIANTI CLASSICO , CHIANTI , COOKING CLASS , VIEWS , LANDSCAPE  …see more

18 Photos

Farmhouse | 1 Bedroom | sleeps 3

Min stay varies

Add to shortlist

from £49 /night

£342 - £813 / week

View

Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
CHIANTI , SWIMMING POOL , VIEW , COOKING CLASS, AGRITURISMO , NATURE , RELAX , LANDSCAPE , WINE  …see more

23 Photos

Farmhouse | 2 Bedrooms | sleeps 5

Min stay varies

Add to shortlist

from £86 /night

£599 - £1112 / week

View

Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
CHIANTI , WINE , COOKING CLASS , AGRITURISMO , LANDSCAPE , VIEW  …see more

20 Photos

House | 4 Bedrooms | sleeps 5

Very Good 4/5 

Min stay varies

Add to shortlist

Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
CASALTA di PESA: Beautiful stone Tuscan hamlet in 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 beauties of the surrounding landscape. Casalta di Pesa is an Holiday Home surrounded by vineyards, just outside Castellina in Chianti  …see more