Horse riding holiday villas and apartments Gaiole in Chianti | Holiday Lettings

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  • Italy
  • Tuscany
  • Province of Siena
  • Gaiole in Chianti

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  • Lecchi (6)
  • Montefienali (1)
  • Montegrossi (1)

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45 Holiday homes

Filters applied: Horse riding (45)

Travellers going to Gaiole in Chianti are booking August dates now. Secure your holiday home today and have the perfect trip.

(2) Excellent 

1 / 18

Tuscany / Province of Siena / Gaiole in Chianti

2 bedroomsSleeps 27 nights min stay

  • 2 bedrooms
  • Sleeps 2
  • 7 nights min stay
Key info: Swimming pool; Suitable for children age 5+; Pets welcome;
 …see more

from £75 / night

£525 - £800 / week

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from £75 / night

(32) Excellent 

1 / 24

1 bedroom luxury apartment with Private Garden, Gaiole in Chianti

Tuscany / Province of Siena / Gaiole in Chianti

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Not suitable for children; Car advised;
Surrounded by the famous rolling hills covered with vineyards and olive groves, which give the name to some of the most prestigious Chianti wine is Borgo di Gaiole. The apartment is on the ground floor as you enter the Borgo, private and self contained around 60sq meter  …see more

from £90 / night

£630 - £770 / week

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from £90 / night

(5) Very Good 

1 / 23

Spacious Chianti apartment with pool access, terrace and outdoor dining area

Tuscany / Province of Siena / Gaiole in Chianti

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 0 km; Swimming pool; Great for children of all ages ;
This is a spacious fully furnished 2 bedroom apartment in Borgo di Gaiole in the village of Gaiole in Chianti. Gaiole is in the heart of the Chianti Classico Region of Tuscany.The property has stunning views over the village and to the vineyards overlooking the village  …see more

from £100 / night

£600 - £850 / week

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from £100 / night

(14) Excellent 

1 / 22

Casacorvo Minore *Late Booking Discounts*

Tuscany / Province of Siena / Gaiole in Chianti

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 80 km; Swimming pool; Great for children of all ages ;
Set in the Chianti Hills just 30 mins from Siena is Borgo di Gaiole, situated on the edge of Gaiole in Chianti, one of the historic 'Chianti League' townships.The Borgo comprises the best of old and new. Built in traditional Tuscan architectural style with sol  …see more

from £85 / night

£525 - £725 / week

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from £85 / night

(11) Excellent 

1 / 27

Villa LisiDor, luxury Tuscany cottage in Chianti

Tuscany / Province of Siena / Gaiole in Chianti

4 bedroomsSleeps 107 nights min stay

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Nearest beach 110 km; Swimming pool; Great for children of all ages ;
VILLA LISIDOR: FULLY RENOVATED WITH ALL NEW AMENITIES. The habitable area is doubled: from 150 square meters to 300 square meters. On GROUND FLOOR, which is at garden level, is a large sitting room with Tv Sat area, a dining room in front of the pool, a professional  …see more

from £395 / night

£2763 - £4250 / week

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from £395 / night

1 / 24

Casa Chianti - Gaiole in Chianti apartment sleeps 3

Tuscany / Province of Siena / Gaiole in Chianti

1 bedroomSleeps 37 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 7 nights min stay
Key info: Nearest beach 105 km; Swimming pool; Great for children of all ages ;
A cosy and lovingly furnished 1 bedroom apartment located in the spectacular Borgo di Gaiole, a popular hamlet just a short walk from the centre of the renown Gaiole in Chianti, right in the heart of the Chianti region, and only 20 minutes away from the wonderful SienaT  …see more

from £43 / night

£300 - £517 / week

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from £43 / night

1 / 18

Tuscany / Province of Siena / Gaiole in Chianti

3 bedroomsSleeps 5Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Great for children of all ages ; Car advised; Some pets are welcome - please contact the owner;
 …see more

from £46 / night

£300 - £500 / week

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from £46 / night

1 / 22

Casa Borgo - Gaiole in Chianti apartment sleeps 4

Tuscany / Province of Siena / Gaiole in Chianti

1 bedroomSleeps 47 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 7 nights min stay
Key info: Nearest beach 105 km; Swimming pool; Great for children of all ages ;
This beautiful and tastefully furnished 1 bedroom apartment is located in the spectacular Borgo di Gaiole, a popular hamlet just a short walk from the centre of the renown Gaiole in Chianti, right in the heart of the Chianti region, and only 20 minutes away from the won  …see more

from £43 / night

£300 - £575 / week

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from £43 / night

1 / 24

Casa Corte - Gaiole in Chianti apartment sleeps 6

Tuscany / Province of Siena / Gaiole in Chianti

2 bedroomsSleeps 67 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 105 km; Swimming pool; Suitable for children age 5+;
This beautiful and tastefully furnished 2 bedroom apartment is located in the spectacular Borgo di Gaiole, a popular hamlet just a short walk from the centre of the renown Gaiole in Chianti, right in the heart of the Chianti region, and only 20 minutes away from the won  …see more

from £47 / night

£325 - £692 / week

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from £47 / night

(12) Excellent 

1 / 23

Casacorvo Maggiore: *Eroica Weekend Available*

Tuscany / Province of Siena / Gaiole in Chianti

3 bedroomsSleeps 84 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
A spacious well furnished three double bedroom, two bathroom apartment with an eight seating dining room and large lounge, just a few minutes stroll from the restaurants, cafes and wide range of services provided by Gaiole village. Outside, enjoy a game of boules in the  …see more

from £165 / night

£1000 - £1500 / week

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from £165 / night

(3) Very Good 

1 / 24

Villa Gaiole - Gaiole in Chianti villa sleeps 8

Tuscany / Province of Siena / Gaiole in Chianti

3 bedroomsSleeps 87 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Nearest beach 107 km; Swimming pool; Great for children of all ages ;
Beautiful Family Villa in Borgo di Gaiole, surrounded by the Chianti hills covered in vineyards and olive groves, just a 100 meters walk from the quiet village of Gaiole in Chianti, a typical Tuscan hamlet with restaurants, shops and amenities, an ideally located betwee  …see more

from £81 / night

£567 - £1359 / week

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from £81 / night

1 / 17

Galassia 22 - Gaiole in Chianti apartment sleeps 4

Tuscany / Province of Siena / Gaiole in Chianti

2 bedroomsSleeps 46 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 6 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
The natural extension of the existing village of Gaiole in Chianti. The 'village-inside-the village' concept that is unique of its kind. The village concept that becomes an integral part of Gaiole in Chianti. Details and the architecture are carefully planned.  …see more

from £109 / night

£659 / week

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from £109 / night

(1) Excellent 

1 / 20

Casa Giardino - Gaiole in Chianti apartment sleeps 3

Tuscany / Province of Siena / Gaiole in Chianti

1 bedroomSleeps 37 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 7 nights min stay
Key info: Nearest beach 105 km; Swimming pool; Great for children of all ages ;
A cosy and lovingly furnished 1 bedroom apartment located in the spectacular Borgo di Gaiole, a popular hamlet just a short walk from the centre of the renown Gaiole in Chianti, right in the heart of the Chianti region, and only 20 minutes away from the wonderful SienaT  …see more

from £43 / night

£300 - £517 / week

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from £43 / night

1 / 16

Tuscany / Province of Siena / Gaiole in Chianti / Lecchi

5 bedroomsSleeps 181 night min stay

  • 5 bedrooms
  • Sleeps 18
  • 1 night min stay
Key info: Nearest beach 130 km; Swimming pool; Great for children of all ages ;
 …see more

from £325 / night

£2246 - £2584 / week

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from £325 / night

1 / 19

Tuscany / Province of Siena / Gaiole in Chianti / Lecchi

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Suitable for children age 5+; Some pets are welcome - please contact the owner;
 …see more

from £60 / night

£425 - £867 / week

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from £60 / night

(1) Excellent 

1 / 22

Tuscany / Province of Siena / Gaiole in Chianti

6 bedroomsSleeps 147 nights min stay

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
 …see more

from £239 / night

£1667 - £2667 / week

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from £239 / night

1 / 24

Ancient castle in the heart of Tuscany, 6 bedrooms

Tuscany / Province of Siena / Gaiole in Chianti / Lecchi

6 bedroomsSleeps 147 nights min stay

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
A dive into an ancient culture in the heart of Tuscany, the Chianti Classico.Il Castello Medievale is situated in a medieval hamlet, constructed of white stone, built around 1000AD, surrounded by forests and olive groves, immersed in a magical atmosphere of tranquility.  …see more

from £400 / night

£2800 - £4309 / week

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from £400 / night

(1) Good 

1 / 23

castello in Chianti conte - Lecchi apartment sleeps 5

Tuscany / Province of Siena / Gaiole in Chianti / Lecchi

2 bedroomsSleeps 53 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min stay
Key info: Swimming pool; Suitable for children age 5+; Car essential;
This lovely 11th century castle for holiday rental in the Chianti Classico area is a tiny, medieval hamlet located at 10 km from Gaiole in Chianti. Built around the year 1000 by the noble family of Guidi, today it is an esteemed wine estate with self catering holiday ap  …see more

from £84 / night

£434 - £575 / week

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from £84 / night

1 / 25

Podere Scopeto - Gaiole in Chianti farmhouse sleeps 12

Tuscany / Province of Siena / Gaiole in Chianti

6 bedroomsSleeps 123 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 3 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
Podere Scopeto is a former Chianti hill farm on the west-facing slopes of the Montagni di Chianti. The present owners bought it some 15 years ago and restored the farmhouse and a separate self-contained studio for family holidays. It has kept its family feel and charm.  …see more

from £350 / night

£2300 - £2800 / week

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from £350 / night

(11) Very Good 

1 / 24

Villa PetrAlexa, Tuscany cottage in Chianti area

Tuscany / Province of Siena / Gaiole in Chianti

3 bedroomsSleeps 77 nights min stay

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min stay
Key info: Nearest beach 110 km; Swimming pool; Great for children of all ages ;
Come to enjoy the typical architecture of Tuscany houses! Villa PetrAlexa is an antic, now renovated barn, with natural stone, original beam ceilings and glass doors which offer a pleasing mix in a comfortable, spacious environment spread over two floors with a wide at  …see more

from £172 / night

£1200 - £2000 / week

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from £172 / night

(1) Good 

1 / 25

castello in Chianti ginestra - Lecchi apartment sleeps 5

Tuscany / Province of Siena / Gaiole in Chianti / Lecchi

2 bedroomsSleeps 53 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
This lovely 11th century castle for holiday rental in the Chianti Classico area is a tiny, medieval hamlet located at 10 km from Gaiole in Chianti. Built around the year 1000 by the noble family of Guidi, today it is an esteemed wine estate with self catering holiday ap  …see more

from £84 / night

£434 - £575 / week

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from £84 / night

1 / 48

Tuscany / Province of Siena / Gaiole in Chianti

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Nearest beach 100 km; Swimming pool; Great for children of all ages ;
 …see more

from £87 / night

£609 - £771 / week

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from £87 / night

1 / 48

Bed & Breakfast La Cerreta - Gaiole in Chianti b&b sleeps 10

Tuscany / Province of Siena / Gaiole in Chianti

5 bedroomsSleeps 10Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Ask owner if suitable for children; Some pets are welcome - please contact the owner;
This beautifull restructured 16th century house sits on a hillside and dominates the sorrounding countryside as far as the eye can see. Nestled in the heart of Chianti our B&B is perfectly located for the week-end break, walking or cycling holidays as well as trekking a  …see more

from £59 / night

£0 / week

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from £59 / night

(1) Excellent 

1 / 12

Il Mulinaccio - Gaiole in Chianti farmhouse sleeps 18

Tuscany / Province of Siena / Gaiole in Chianti

5 bedroomsSleeps 18Min stay varies

  • 5 bedrooms
  • Sleeps 18
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
On entering the property, guests will find a welcoming living area, furnished with sofas around a traditional, focal fireplace. The kitchen is adjacent to this room. The kitchen is a typical Tuscan kitchen, well-equipped with plenty of pots and pans for those that enjoy  …see more

from £465 / night

£3250 - £4500 / week

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from £465 / night

(2) Excellent 

1 / 45

Tuscany / Province of Siena / Gaiole in Chianti

3 bedroomsSleeps 7Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
Key info: Nearest beach 75 km; Swimming pool; Great for children of all ages ;
 …see more

from £125 / night

£0 / week

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from £125 / night

(1) Very Good 

1 / 11

Tuscany / Province of Siena / Gaiole in Chianti

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Great for children of all ages ; No pets allowed;
 …see more

from £67 / night

£400 - £625 / week

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from £67 / night

(1) Very Good 

1 / 17

Villa Brolio - Gaiole in Chianti villa sleeps 12

Tuscany / Province of Siena / Gaiole in Chianti

6 bedroomsSleeps 127 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Nearest beach 125 km; Swimming pool; Great for children of all ages ;
The building of Villa Brolio was originally an old XII century watchtower later transformed into a mill and finally restored to become a villa. The restoration works have been done preserving carefully all the ancient characteristics such as the outside stones, the vau  …see more

from £225 / night

£1575 - £3459 / week

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from £225 / night

(9) Very Good 

1 / 58

Villa Albizi Holidayhome Gaiole in Chianti Tuscany

Tuscany / Province of Siena / Gaiole in Chianti / Montefienali

7 bedroomsSleeps 18Min stay varies

  • 7 bedrooms
  • Sleeps 18
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
NEW MANAGEMENT from Summer 2015 Villa Albizi Tuscany life and more….for groups of friends or large families Villa Albizi is normally rented on a villa-only weekly basis and are ideal for those seeking independence and privacy. We have created a formula designed to  …see more

from £300 / night

£2084 - £4917 / week

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from £300 / night

1 / 27

La Pieve Marsina - Gaiole in Chianti villa sleeps 5

Tuscany / Province of Siena / Gaiole in Chianti

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 70 km; Swimming pool; Great for children of all ages ;
In the top of a hill set in the patchwork of vineyards that characterizes the area of Chianti Classico, in the heart of an ancient medieval village, was born a few years ago Pieve Marsina.The structure, made up of nice apartments, has as principal objective to allow our  …see more

from £117 / night

£817 - £1109 / week

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from £117 / night

(6) Excellent 

1 / 20

2 bedroom apartment in traditional Tuscan complex in village of Gaiole, sleeps 6, shared pool

Tuscany / Province of Siena / Gaiole in Chianti

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car advised;
A fabulous place to relax, this apartment is at the edge of the Borgo furthest from the road. Designed in a traditional style incorporating a range of modern comforts and facilities, the apartment is the best of both worlds. Stone tiled floors with chestnut beams overhe  …see more

from £70 / night

£500 - £700 / week

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from £70 / night

1 / 10

Tuscany / Province of Siena / Gaiole in Chianti

1 bedroomSleeps 41 night min stay

  • 1 bedroom
  • Sleeps 4
  • 1 night min stay
Key info: Nearest beach 100 km; Swimming pool; Great for children of all ages ;
 …see more

from £84 / night

£542 / week

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from £84 / night

1 / 16

Holidayhome Casa Isa, Borgo San Vincenti,Tuscany

Tuscany / Province of Siena / Gaiole in Chianti

3 bedroomsSleeps 5Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
A dream home set in the heart of Chianti. Relax, landscapes, nature, good food, wine ... for a unique holiday! Borgo San Vincenti is composed not only from Casa Isabella: Casa Guia( 4guests);Casa Eolo( 4 guests); Casa Monte Cristo (4 guests) , Casa Maestrale (8 guests)  …see more

from £109 / night

£759 - £1225 / week

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from £109 / night

1 / 13

Casa Ciaccheri - Gaiole in Chianti apartment sleeps 4

Tuscany / Province of Siena / Gaiole in Chianti

2 bedroomsSleeps 43 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
The house is located in the heart of the Chianti Classico, inside the town of Gaiole in Chianti (all kinds of shops). The apartment is on the ground floor and is part of a building where the owners reside.Outside a portion of an equipped courtyard is available for the e  …see more

from £67 / night

£292 / week

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from £67 / night

(1) Excellent 

1 / 24

Casacorvo Grande *Group Discounts* - Gaiole in Chianti apartment sleeps 10

Tuscany / Province of Siena / Gaiole in Chianti

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Nearest beach 80 km; Swimming pool; Great for children of all ages ;
Casacorvo Grande is a townhouse that sits on the edge of the unique development of Borgo di Gaiole overlooking the Chianti Hills. It is a perfect location for a holiday. The accommodation comprises of two apartments, one 1bed/1bath and one 3bed/2bath, that can be combi  …see more

from £250 / night

£1600 - £2100 / week

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from £250 / night

1 / 20

Tuscany / Province of Siena / Gaiole in Chianti

3 bedroomsSleeps 57 nights min stay

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Swimming pool; Suitable for children age 5+; Some pets are welcome - please contact the owner;
 …see more

from £78 / night

£542 / week

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from £78 / night

1 / 33

Tuscany / Province of Siena / Gaiole in Chianti

3 bedroomsSleeps 63 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Great for children of all ages ; Car advised; No pets allowed;
 …see more

from £100 / night

£700 / week

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from £100 / night

1 / 14

Tuscany / Province of Siena / Gaiole in Chianti

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
 …see more

from £77 / night

£0 / week

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from £77 / night

1 / 19

Tuscany / Province of Siena / Gaiole in Chianti

2 bedroomsSleeps 52 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min stay
Key info: Suitable for children age 5+; Car advised; Air conditioning;
 …see more

from £350 / night

£1250 / week

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from £350 / night

1 / 20

Tuscany / Province of Siena / Gaiole in Chianti

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
 …see more

from £81 / night

£567 / week

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from £81 / night

1 / 24

Casa Lecchi - Gaiole in Chianti apartment sleeps 4

Tuscany / Province of Siena / Gaiole in Chianti

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Pets welcome;
Casa Lecchi is a spacious two bedroom apartment facing on to the main piazza of Montefiorile which is a small hamlet of 14 villas situated in a quiet position in the heart of the Chianti Classico wine producing area. The hamlet is on a hillside and the houses enjoy st  …see more

from £61 / night

£425 - £934 / week

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from £61 / night

Top Destination reviews

Villa PetrAlexa, Tuscany cottage in Chianti area
Villa PetrAlexa - excellent leisure facility

This years stay was even better than our stay last year. Despite the fact we arrived late at night due to repeated traffic jams on the motorway because of terrible weather conditions, everything was perfectly prepared. The house was heated up and foo … see more
Perfect, beautifil little place in tuscany

A beautiful place full of happines, were you can stay The time you want for a very very good price ,there's a beautiful view, is very relaxing and you can enjoy The animals and nature … see more

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