List your home
Apply filters
£ to

Holiday homes 28

Reset search

Show results on map

Filter your search

Price per night

Price per night

£ to per night

Bedrooms

Location

  • Italy Clear
  • Tuscany Clear
  • Province of Siena Clear
  • Castellina In Chianti Clear

Location

  • All locations
  • Cagnano di Sotto (1)

more +

less -

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

Filters applied: Horse riding (28)

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
28 Results   |  

Excellent 5/5 

24 Photos

Province of Siena / Castellina In Chianti

Villa / 7 Bedrooms / sleeps 14

Excellent 5/5 

5 Nights min stay

Add to shortlist

from £388 / night

£2713 - £3274 / week

View

Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
Sleeps 14 with possibility to add adjacent apartments up to total of 33. A beautiful 15th-century villa in the heart of the Chianti countryside, with 360° uninterrupted views of olives, vines and forests, with amazing sunset views over San Gimignano and the Apennine  …see more


23 Oct 2014

5/5

"Peaceful, Beautiful, Great hospitality"

Our hosts, Simon and Verity, were marvels of hosting. They made sure we were comfortable and knew the ins and outs. They were hospitable without being intrusive. A true skill. The accommodations w… More

See all reviews Continue

48 Photos

Province of Siena / Castellina In Chianti

Cottage / 2 Bedrooms / sleeps 4

4 Nights min stay

Add to shortlist

from £56 / night

£391 - £596 / 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: cou  …see more

13 Photos

Province of Siena / Castellina In Chianti

Cottage / 1 Bedroom / sleeps 2

1 night min stay

Add to shortlist

from £91 / night

£632 - £766 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
  • Private garden
Beautiful cottage with private garden and access to pool with amazing sunset views  …see more

Featured properties

11 Photos

Province of Siena / Castellina In Chianti

Villa / 4 Bedrooms / sleeps 7

3 Nights min stay

Add to shortlist

from £147 / night

£1029 - £1774 / week

View

Key info:

  • Great for children of all ages
  • Car essential
  • No pets allowed
Il Torrino is a wonderful 4 bedroom villa set within a small and perfectly kept Tuscan medieval village and situated atop a hill with stunning views over the Chianti vineyards. Once a Medieval watch tower, the property oozes character and charm, but has been completely  …see more

9 Photos

Province of Siena / Castellina In Chianti

Apartment / 1 Bedroom / sleeps 2

1 night min stay

Add to shortlist

from £97 / night

£674 - £866 / week

View

Key info:

  • Swimming pool
  • Suitable for children over 5
  • No pets allowed
Beautiful and typical apartment for 2/4 people located inside a wine farm up to a Chianti hill, close to Siena. The resort has also a restaurant that propose tuscan receipts, an enchanting swimming pool overlooking the valley  …see more

24 Photos

Province of Siena / Castellina In Chianti

Apartment / 2 Bedrooms / sleeps 8

3 Nights min stay

Add to shortlist

from £79 / night

£547 - £586 / week

View

Key info:

  • Nearest beach 90 km
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Large, elegant, comfortable apartment in incomparable surroundings. Peaceful and relaxing with spectacular scenery. 3 km from Castellina in Chianti with its medieval town centre, shops, bars, restaurants. 22 km from Siena., 37km from Florence. No neighbours or noise. P  …see more

24 Photos

Province of Siena / Castellina In Chianti

Farmhouse / 2 Bedrooms / sleeps 6

3 Nights min stay

Add to shortlist

from £122 / night

£852 - £1490 / 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

Province of Siena / Castellina In Chianti

Farmhouse / 2 Bedrooms / sleeps 6

3 Nights min stay

Add to shortlist

from £61 / night

£426 - £1064 / 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

16 Photos

Castellina In Chianti / Cagnano di Sotto

Apartment / 2 Bedrooms / sleeps 4

7 Nights min stay

Add to shortlist

from £46 / night

£318 - £462 / week

View

Key info:

  • Nearest beach 85 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
TUSCAN STYLE STONE MADE APARTMENT WITH TERRACE OUTDOOR EATING SPACE AND POOL TO SHARE WITH TWO BEDROOMS THAT CAN ACCOMMODATE 4 ADULTS, THIS HOUSE IS SURROUND BY GREEN. HEART OF CHIANTI , PEACEFUL RELAXING AREA, PERFECTLY LOCATED TO TOUR AROUND  …see more

Excellent 5/5 

24 Photos

Province of Siena / Castellina In Chianti

Villa / 3 Bedrooms / sleeps 7

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £139 / night

£969 - £1137 / week

View

Key info:

  • Nearest beach 85 km
  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
The Cypresses Villa is a real amazing place, peaceful, green, sunny, a great place for families and also for a small group of friends.There is a large list of sites to visit around, it is a perfect spot in between Sienna and Florence, an ideal postcard of Tuscany.  …see more


13 Mar 2015

5/5

"Charming staying and great location"

Cypresses Villa was the perfect house to stay for us, my wife and I had peaceful and relaxing time sitting outside, drinking a wine and reading, while the kids had great time in the fields, it was eve… More

See all reviews Continue

22 Photos

Province of Siena / Castellina In Chianti

B&B / 13 Bedrooms / sleeps 2

1 night min stay

Add to shortlist

from £61 / night

£422 - £547 / 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

29 Photos

Province of Siena / Castellina In Chianti

Apartment / 2 Bedrooms / sleeps 5

2 Nights min stay

Add to shortlist

from £91 / night

£632 - £986 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Le colline del Chianti a bordo piscina, il nostro giardino privato per le vostre cene estive, il barbecue e forno a legna, il camino, la chiesetta, i laghetti, il comfort e la pace... Chianti Suite Borgo Quornia offre tutto questo e soggiornarvi sarà un incanto!  …see more

21 Photos

Province of Siena / Castellina In Chianti

Apartment / 2 Bedrooms / sleeps 6

7 Nights min stay

Add to shortlist

from £52 / night

£358 - £706 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Granaio 2: trilocale di 85 mq. composto al pianterreno da zona pranzo-soggiorno con angolo cottura, camino e divano letto. Al piano superiore una camera matrimoniale, una camera con due letti singoli che possono essere accoppiati per formare un matrimoniale, ed un bagno  …see more

13 Photos

Province of Siena / Castellina In Chianti

Apartment / 2 Bedrooms / sleeps 4

7 Nights min stay

Add to shortlist

from £50 / night

£348 - £648 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Melograno: appartamento di mq. 75 circa composto da cucinotto, zona pranzo-soggiorno con divano letto, una camera matrimoniale, una camera con due letti accoppiabili, bagno con doccia e spazio privato esterno arredato con mobili da giardino.  …see more

17 Photos

Province of Siena / Castellina In Chianti

Apartment / 1 Bedroom / sleeps 4

7 Nights min stay

Add to shortlist

from £31 / night

£213 - £355 / week

View

Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Car advised
  • Some pets are welcome - please contact the owner
CASTELLINA IN CHIANTI  …see more

16 Photos

Province of Siena / Castellina In Chianti

Condo / 9 Bedrooms / sleeps 16

Short stays welcome

Add to shortlist

from £355 / night

£2483 / 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

13 Photos

Province of Siena / Castellina In Chianti

House / 2 Bedrooms / sleeps 6

7 Nights min stay

Add to shortlist

from £108 / night

£750 - £950 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
Italy, Tuscany, Chianti, Castellina in Chianti, Florence, swimming pool, tennis court, private garden, stunning views, Luxury interior designed, house, beautiful gardens, San Gimignano, Siena, Florence, Firenze.  …see more

16 Photos

Province of Siena / Castellina In Chianti

Castle / 2 Bedrooms / sleeps 4

3 Nights min stay

Add to shortlist

from £113 / night

£785 - £1321 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Relais chianti, luxury apartment chianti, hamlet chianti, medieval village, infinity swimming pool ,outdoor dining area , barbecue grill.  …see more

24 Photos

Province of Siena / Castellina In Chianti

Villa / 6 Bedrooms / sleeps 12

7 Nights min stay

Add to shortlist

from £472 / night

£3298 / 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

14 Photos

Province of Siena / Castellina In Chianti

Apartment / 2 Bedrooms / sleeps 5

5 Nights min stay

Add to shortlist

from £126 / night

£880 - £1160 / week

View

Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
Le Stalle is a lovely 2-bedroom apartment situated on the ground floor of Podere Patrignone, a 15th century farmhouse in the heart of Chianti, surrounded on all sides by olives, vines, hills and forest. It has a kitchen, dining area, outside porch and use of the pool.  …see more

23 Photos

Province of Siena / Castellina In Chianti

Farmhouse / 2 Bedrooms / sleeps 5

Min stay varies

Add to shortlist

Pricing unknown

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

14 Photos

Province of Siena / Castellina In Chianti

Farmhouse / 2 Bedrooms / sleeps 7

Min stay varies

Add to shortlist

Pricing unknown

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

14 Photos

Province of Siena / Castellina In Chianti

Farmhouse / 1 Bedroom / sleeps 4

Min stay varies

Add to shortlist

Pricing unknown

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

Province of Siena / Castellina In Chianti

Farmhouse / 1 Bedroom / sleeps 3

Min stay varies

Add to shortlist

Pricing unknown

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

14 Photos

Province of Siena / Castellina In Chianti

Apartment / 2 Bedrooms / sleeps 6

7 Nights min stay

Add to shortlist

from £44 / night

£308 - £611 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Tinaia: trilocale di mq.70 circa composto da zona pranzo-soggiorno con angolo cottura e divano letto, una camera matrimoniale, una camera con due letti accoppiabili, bagno con doccia e spazio privato esterno arredato con mobili da giardino.  …see more

16 Photos

Province of Siena / Castellina In Chianti

Townhouse / 1 Bedroom / sleeps 4

7 Nights min stay

Add to shortlist

from £40 / night

£279 - £519 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Quercia: appartamento di 55 mq. composto da ampio soggiorno con divano letto, angolo cottura, camera matrimoniale e bagno con doccia.  …see more

18 Photos

Province of Siena / Castellina In Chianti

Townhouse / 3 Bedrooms / sleeps 8

7 Nights min stay

Add to shortlist

from £71 / night

£497 - £887 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Alloro: appartamento di 100 mq su due piani, composto al pian terreno da zona pranzo-soggiorno con divano letto, camino e cucinotto, una camera matrimoniale, una camera con due letti singoli che possono essere accoppiati per formare un matrimoniale, ed un bagno con docc  …see more

18 Photos

Province of Siena / Castellina In Chianti

Apartment / 1 Bedroom / sleeps 4

7 Nights min stay

Add to shortlist

from £40 / night

£279 - £519 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Granaio 1: bilocale di 55 mq. composto da ampio soggiorno con divano letto, angolo cottura e camino. Al piano superiore la camera matrimoniale ed il bagno con doccia.  …see more

Don’t let an old browser slow down your holiday

Your browser is out of date and might not work well with our website. Download the latest version to speed up your hunt for the perfect holiday home.

Just click on the icons to get to the download page