List your home
Apply filters
£ to

99 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
2,500 properties
Florence
980 properties
Venice, Veneto
488 properties
Trapani
476 properties
Amalfi Coast
453 properties
Lucca
438 properties
Palermo
412 properties
Cortona
411 properties
Sorrento, Campania
351 properties
Cefalu
315 properties
San Gimignano
288 properties
Taormina
275 properties
Greve in Chianti
262 properties
Massa Lubrense
245 properties
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
99 Results  |  
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

24 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

Add to shortlist

from £49 /night

£341 - £446 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
This former farm - where at the end of the 19th century pasta was produced and sold - is a green oasis in the rural village of Greve, in Chianti. Situated not far from restaurants, cafes, shops and the historic square of the village, you can enjoy its tranquil garden...  …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 5
  • Car not necessary
  • Pets welcome
  • Private garden
Apartment for 6 persons, with swimming pool , in Chianti  …see more

Featured properties

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 | 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 5
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Castellina In Chianti with 2 bedrooms sleeps 4  …see more

13 Photos

Villa | 2 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £167 /night

£1165 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
Holiday house for 6 persons, with swimming pool , in Chianti  …see more

16 Photos

Apartment | 2 Bedrooms | sleeps 5

7 Nights min stay

Add to shortlist

from £68 /night

£470 - £627 / week

View

Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • No pets allowed
  • Private garden
Attractive apartment for 5 persons, with swimming pool , in Chianti  …see more

16 Photos

Villa | 6 Bedrooms | sleeps 11

2 Nights min stay

Add to shortlist

from £432 /night

£3023 - £4763 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

20 Photos

Villa | 7 Bedrooms | sleeps 14

2 Nights min stay

Add to shortlist

from £295 /night

£2061 - £3845 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

24 Photos

Apartment | 1 Bedroom | sleeps 3

7 Nights min stay

Add to shortlist

from £41 /night

£281 - £396 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
This wonderful holiday accommodation is situated on the site of the former 12th century castle of Monte Gonzi. Occupying a strategic location between Florence and Siena, the castle once dominated this part of the Chianti region. In the construction of the current hou...  …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 5
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Castellina In Chianti with 1 bedrooms sleeps 2  …see more

21 Photos

Apartment | 1 Bedroom | sleeps 4

7 Nights min stay

Add to shortlist

from £62 /night

£434 - £578 / week

View

Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • No pets allowed
  • Private garden
Attractive apartment for 4 persons, with swimming pool , in Chianti  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 7

7 Nights min stay

Add to shortlist

from £77 /night

£536 - £702 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
This wonderful holiday accommodation is situated on the site of the former 12th century castle of Montegonzi. Thanks to its strategic location between Florence and Siena, the castle once dominated this part of the Chianti region. In the construction of the current ho...  …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 5
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Castellina In Chianti with 4 bedrooms sleeps 8  …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 5
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Castellina In Chianti with 2 bedrooms sleeps 4  …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 5
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Castellina In Chianti with 1 bedrooms sleeps 4  …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 5
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Castellina In Chianti with 2 bedrooms sleeps 4  …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 5
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Castellina In Chianti with 3 bedrooms sleeps 5  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £64 /night

£446 - £536 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
This wonderful holiday accommodation is situated on the site of the former 12th century castle of Monte Gonzi. Occupying a strategic location between Florence and Siena, the castle once dominated this part of the Chianti region. In the construction of the current hou...  …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 5
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Castellina In Chianti with 6 bedrooms sleeps 13  …see more

14 Photos

Apartment | 3 Bedrooms | sleeps 6

1 night min stay

Add to shortlist

from £134 /night

£936 - £1101 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • No pets allowed
  • Private garden
Villa Sidonia is a pleasant and spacious apartment in the characteristic style of the Tuscan countryside. It sleeps six people. It is appoximately 90 square meters (970 square feet)  …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 5
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Castellina In Chianti with 1 bedrooms sleeps 2  …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 5
  • Some pets are welcome - please contact the owner
  • Private garden
Apartment / Condo 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 5
  • 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

24 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £96 /night

£672 - £1124 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car not necessary
  • No pets allowed
Apartment for 4 persons, with swimming pool , in Chianti  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £155 /night

£1084 - £1463 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
Carming apartments in a medieval hamlet in heart of Tuscany, all the apartments have been carefully restored, swimming pool  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 12

7 Nights min stay

Add to shortlist

from £325 /night

£2270 - £4257 / week

View

Key info:

  • Nearest beach 85 km
  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
This extraordinary villa welcomes up to 12 people in its ample common areas and bedrooms, and it has a wonderful garden and swimming pool. It is ideal for large families or groups of friends.  …see more

17 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £256 /night

£1790 - £3951 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
This gorgeous house, with 5 bedrooms and 6 bathrooms can host 10 people, so it is ideal for a large group of friends. Located in Tuscany Italy, this house has a swimming pool.  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

3 Nights min stay

Add to shortlist

from £262 /night

£1831 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
This grand house, with 5 bedrooms and 5 bathrooms can host 10 people, so it is ideal for large families. Located in Tuscany Italy, this house offers a swimming Pool, an internet Connection .  …see more

24 Photos

Villa | 8 Bedrooms | sleeps 16

7 Nights min stay

Add to shortlist

from £366 /night

£2557 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
elegant house sleeps 16 people, so it is ideal for a large group of friends to enjoy an unforgettable trip to Chianti. The villa offers a swimming pool and an internet Connection.  …see more

6 Photos

House | 4 Bedrooms | sleeps 9

7 Nights min stay

Add to shortlist

from £174 /night

£1216 - £2486 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
Once a fine old 17th century Tuscan barn, this beautiful, restored property has its own private swimming pool. The house lies in its own grounds with views over Tuscany, and on a clear day the towers of San Gimignano are visible on the horizon. There is a small villa...  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £177 /night

£1237 - £1688 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
Carming apartments in a medieval hamlet in heart of Tuscany, all the apartments have been carefully restored, swimming pool  …see more

17 Photos

House | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £63 /night

£436 - £1007 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
This property is made up of three great apartments, with independent entrances, one of which is inhabited by the owners, in a beautiful and characteristic farmhouse in the heart of the Chianti Classico, set in a landscape rich in vineyards and olive groves. From here...  …see more

21 Photos

Villa | 6 Bedrooms | sleeps 12

7 Nights min stay

Add to shortlist

from £256 /night

£1790 - £3951 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
Set in Tuscany Italy, this lovely house is the perfect place for your holidays. The house has a swimming pool and an internet connection.  …see more

13 Photos

House | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £74 /night

£516 - £1066 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
This property is made up of three great apartments, with independent entrances, one of which is inhabited by the owners, in a beautiful and characteristic farmhouse in the heart of the Chianti Classico, set in a landscape rich in vineyards and olive groves. From here...  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

Add to shortlist

from £428 /night

£2995 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
This luxury villa for 8 in beautiful Chianti is ideally located between Florence and Siena. It is a truly stunning property set in peaceful grounds including a swimming pool, gardens and olive grove. Inside it is just attractive featuring 4 large en  …see more

24 Photos

Villa | 2 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £156 /night

£1089 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
This elegant house, with 2 bedrooms and 3 bathrooms can accomodate 6 people, so it is perfect for a large group of friends. Located in Tuscany Italy, this house offers a swimming Pool, air Conditioning .  …see more

24 Photos

Villa | 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 5
  • Air conditioning
  • No pets allowed
Located in Tuscany Italy, this gorgeous accommodation is the perfect place for your holidays. The accommodation features: a swimming Pool, air Conditioning .  …see more

24 Photos

Villa | 8 Bedrooms | sleeps 16

7 Nights min stay

Add to shortlist

from £381 /night

£2662 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
elegant house sleeps 16 people, so it is perfect for a large group of friends and is located in Tuscany Italy. This property is ideal if you seek a relaxing holiday. The villa features: a swimming Pool, air Conditioning, an internet Connection .  …see more

18 Photos

B&B | 13 Bedrooms | sleeps 2

1 night min stay

Add to shortlist

from £73 /night

£509 - £587 / week

View

Key info:

  • Nearest beach 50 km
  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
  • Private garden
Romantic B&B in the heart of Tuscany..... Charming farmhouse, harmoniously situated in the traditional and magical frame of the Chianti hills..  …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 5
  • 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 5
  • 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 5
  • 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 5
  • 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

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 5
  • Car essential
  • Pets welcome
CHIANTI , SWIMMING POOL , VIEW , COOKING CLASS, AGRITURISMO , NATURE , RELAX , LANDSCAPE , WINE  …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 5
  • Car essential
  • Pets welcome
WINE , CHIANTI CLASSICO , CHIANTI , COOKING CLASS , VIEWS , LANDSCAPE  …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 5
  • Car not necessary
  • Pets welcome
  • Private garden
CHIANTI , WINE , COOKING CLASS , AGRITURISMO , LANDSCAPE , VIEW  …see more

9 Photos

Farmhouse | 2 Bedrooms | sleeps 4

Min stay varies

Add to shortlist

from £74 /night

£513 - £1026 / week

View

Key info:

  • Great for children of all ages 5
  • Car essential
  • No pets allowed
WINE , CHIANTI , VIEW , LANDSCAPE , COOKING CLASS , CASTELLINA IN CHIANTI  …see more

20 Photos

Farmhouse | 6 Bedrooms | sleeps 12

7 Nights min stay

Add to shortlist

from £459 /night

£3210 - £5638 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • No pets allowed
Conveniently located in the heart of Chianti close to Siena. Practical layout. Fantastic views. Helpful owners available for assistance.  …see more