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  • Italy
  • Tuscany
  • Province of Siena
  • Gaiole in Chianti
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  • Lecchi (12)
  • Montefienali (1)
  • Montegrossi (3)

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67 Holiday homes

Filters applied: Pets allowed (67)

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

(13) Excellent 

23

Casacorvo Maggiore: *Eroica Weekend Available* - Gaiole in Chianti apartment sleeps 8

Province of Siena / Gaiole in Chianti

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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

(15) Excellent 

22

Casacorvo Minore *Late Booking Discounts* - Gaiole in Chianti apartment sleeps 4

Province of Siena / Gaiole in Chianti

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
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

Province of Siena / Gaiole in Chianti

3 5 1 night min

  • 3 bedrooms
  • Sleeps 5
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £190 / night

£1164 / week

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from £190 / night

4

Province of Siena / Gaiole in Chianti

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Ask about pets
  • Private garden

 …see more

from £132 / night

£918 / week

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from £132 / night

18

Villa Fontecaresino 1 - Montegrossi villa sleeps 9

Gaiole in Chianti / Montegrossi

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Ask about pets
Fontecaresino, located in the hills of Chianti, in the heart of Tuscany, with ready access to the culinary, cultural and artistic heritage of this region, is only 4 km from Gaiole in Chianti, 35 km from Siena, 45 km from Arezzo and 55 km from Florence. Our close proximi  …see more

from £111 / night

£776 - £1983 / week

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from £111 / night

(6) Excellent 

26

Just 5 minutes from the centre of the Gaiolie, wonderful apartment with pool and breathtaking terrace, sleeps 6 - Gaiole in Chianti apartment sleeps 6

Province of Siena / Gaiole in Chianti

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The apartment is just 5 minutes walk from the center of Gaiole, where you will find all the services you need. Like restaurants, bars, wineshops, banks, food shop, hairdressers etc.Gaiole is one of several traditional Chianti villages in the region. Others worth visitin  …see more

from £85 / night

£595 - £944 / week

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from £85 / night

18

Province of Siena / Gaiole in Chianti

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden

 …see more

from £48 / night

£311 - £518 / week

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from £48 / night

(1) Excellent 

20

Casa Giardino - Gaiole in Chianti apartment sleeps 3

Province of Siena / Gaiole in Chianti

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Nearest beach 105 km
  • Swimming pool
  • Child friendly
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 £45 / night

£311 - £535 / week

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from £45 / night

12

Province of Siena / Gaiole in Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about pets

 …see more

from £60 / night

£518 - £733 / week

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from £60 / night

4

Province of Siena / Gaiole in Chianti

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Ask about pets
  • Private garden

 …see more

from £66 / night

£459 / week

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from £66 / night

24

Casa Corte - Gaiole in Chianti apartment sleeps 6

Province of Siena / Gaiole in Chianti

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • 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 £49 / night

£337 - £716 / week

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from £49 / night

4

Province of Siena / Gaiole in Chianti

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Ask about pets
  • Private garden

 …see more

from £66 / night

£459 / week

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from £66 / night

24

Ancient castle in the heart of Tuscany, 6 bedrooms - Lecchi castle sleeps 14

Gaiole in Chianti / Lecchi

6 14 7 nights min

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • 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 £414 / night

£2897 - £3345 / week

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from £414 / night

25

Podere Scopeto - Gaiole in Chianti farmhouse sleeps 12

Province of Siena / Gaiole in Chianti

6 12 3 nights min

  • 6 bedrooms
  • Sleeps 12
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
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 - £2500 / week

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from £350 / night

22

Casa Borgo - Gaiole in Chianti apartment sleeps 4

Province of Siena / Gaiole in Chianti

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Nearest beach 105 km
  • Swimming pool
  • Child friendly
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 £45 / night

£311 - £595 / week

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from £45 / night

(1) Good 

33

Appartamento Gaiole 40 - Gaiole in Chianti apartment sleeps 4

Province of Siena / Gaiole in Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Appartamento Gaiole 40 is a wonderful apartment in the heart of Chianti. This area is famous all over the world for its typical products and its superb wines. The apartment is located in Borgo di Gaiole, an ancient Borgo recently renovated that enjoys a magnificent view  …see more

from £92 / night

£640 - £981 / week

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from £92 / night

19

Province of Siena / Gaiole in Chianti

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Suitable for children age 5+
  • Air conditioning
  • Ask about pets

 …see more

from £363 / night

£1294 / week

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from £363 / night

24

Casa Chianti - Gaiole in Chianti apartment sleeps 3

Province of Siena / Gaiole in Chianti

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Nearest beach 105 km
  • Swimming pool
  • Child friendly
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 £45 / night

£311 - £535 / week

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from £45 / night

20

Province of Siena / Gaiole in Chianti

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Ask about pets

 …see more

from £81 / night

£561 / week

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from £81 / night

48

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

Province of Siena / Gaiole in Chianti

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask owner if suitable for children
  • Ask about pets
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 £61 / night

£423 / week

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from £61 / night

16

Holidayhome Casa Isa, Borgo San Vincenti,Tuscany - Gaiole in Chianti house sleeps 5

Province of Siena / Gaiole in Chianti

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
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 £113 / night

£785 - £1121 / week

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from £113 / night

19

Gaiole in Chianti / Lecchi

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Ask about pets

 …see more

from £63 / night

£440 - £664 / week

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from £63 / night

20

Villa Fontecaresino 2 - Montegrossi house sleeps 4

Gaiole in Chianti / Montegrossi

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Child friendly
  • Ask about pets
  • Private garden
Fontecaresino, located in the hills of Chianti, in the heart of Tuscany, with ready access to the culinary, cultural and artistic heritage of this region, is only 4 km from Gaiole in Chianti 10 km from Radda in Chianti, 35 km from Siena, 45 km from Arezzo and 55 km from  …see more

from £74 / night

£513 / week

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from £74 / night

(1) Excellent 

12

Il Mulinaccio - Gaiole in Chianti farmhouse sleeps 16

Province of Siena / Gaiole in Chianti

5 16 Min stay varies

  • 5 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
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 £432 / night

£3018 - £4656 / week

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from £432 / night

15

Pievasciata - 44263001 - Lecchi farmhouse sleeps 2

Gaiole in Chianti / Lecchi

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Ancient farmhouse with adjoining barn situated on a large and renowned farming estate producing excellent wine and olive oil. This property has been carefully restored and turned into 6 comfortable apartments, all of which offering nice interiors furnished in a rustic s  …see more

from £97 / night

£620 - £716 / week

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from £97 / night

12

Pievasciata - 44263006 - Lecchi farmhouse sleeps 2

Gaiole in Chianti / Lecchi

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Ancient farmhouse with adjoining barn situated on a large and renowned farming estate producing excellent wine and olive oil. This property has been carefully restored and turned into 6 comfortable apartments, all of which offering nice interiors furnished in a rustic s  …see more

from £92 / night

£582 - £690 / week

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from £92 / night

27

Appartamento Gaiole 15 - Gaiole in Chianti apartment sleeps 2

Province of Siena / Gaiole in Chianti

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Appartamento Gaiole 15 is a wonderful apartment in the heart of Chianti. This area is famous all over the world for its typical products and its superb wines. The apartment is located in Borgo di Gaiole, an ancient Borgo recently renovated that enjoys a magnificent view  …see more

from £61 / night

£423 - £608 / week

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from £61 / night

23

Radda In Chianti - 41968001 - Lecchi farmhouse sleeps 10

Gaiole in Chianti / Lecchi

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Ask about pets
The Villa Gallo Nero is a lovely home offering 5 bedrooms and 5 baths and is situated in the village of Casanuova di Ama. The village is comprised of a small cluster of houses surrounded by vineyards of wine and oil-producing farmers. Centered between the medieval towns  …see more

from £293 / night

£1703 - £2139 / week

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from £293 / night

12

Pievasciata - 44263003 - Lecchi farmhouse sleeps 2

Gaiole in Chianti / Lecchi

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Ancient farmhouse with adjoining barn situated on a large and renowned farming estate producing excellent wine and olive oil. This property has been carefully restored and turned into 6 comfortable apartments, all of which offering nice interiors furnished in a rustic s  …see more

from £96 / night

£620 - £716 / week

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from £96 / night

19

Gaiole In Chianti - 27123003 - Gaiole in Chianti farmhouse sleeps 6

Province of Siena / Gaiole in Chianti

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Beautiful stone hamlet recently restored situated in quiet and panoramic location on the Chianti Classico hills offering extensive views over the surrounding vineyards. This charming hamlet comprises 6 nice apartments (and 9 double bedrooms) all of which furnished in a  …see more

from £184 / night

£1156 - £1651 / week

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from £184 / night

15

Gaiole In Chianti - 27123002 - Gaiole in Chianti farmhouse sleeps 2

Province of Siena / Gaiole in Chianti

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Beautiful stone hamlet recently restored situated in quiet and panoramic location on the Chianti Classico hills offering extensive views over the surrounding vineyards. This charming hamlet comprises 6 nice apartments (and 9 double bedrooms) all of which furnished in a  …see more

from £132 / night

£826 - £1156 / week

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from £132 / night

14

Pievasciata - 44263002 - Lecchi farmhouse sleeps 4

Gaiole in Chianti / Lecchi

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Ancient farmhouse with adjoining barn situated on a large and renowned farming estate producing excellent wine and olive oil. This property has been carefully restored and turned into 6 comfortable apartments, all of which offering nice interiors furnished in a rustic s  …see more

from £126 / night

£820 - £926 / week

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from £126 / night

15

Pievasciata - 44263005 - Lecchi farmhouse sleeps 5

Gaiole in Chianti / Lecchi

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Ancient farmhouse with adjoining barn situated on a large and renowned farming estate producing excellent wine and olive oil. This property has been carefully restored and turned into 6 comfortable apartments, all of which offering nice interiors furnished in a rustic s  …see more

from £154 / night

£969 - £1152 / week

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from £154 / night

14

Pievasciata - 44263004 - Lecchi farmhouse sleeps 2

Gaiole in Chianti / Lecchi

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Ancient farmhouse with adjoining barn situated on a large and renowned farming estate producing excellent wine and olive oil. This property has been carefully restored and turned into 6 comfortable apartments, all of which offering nice interiors furnished in a rustic s  …see more

from £92 / night

£582 - £690 / week

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from £92 / night

17

Gaiole In Chianti - 27123005 - Gaiole in Chianti farmhouse sleeps 6

Province of Siena / Gaiole in Chianti

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Beautiful stone hamlet recently restored situated in quiet and panoramic location on the Chianti Classico hills offering extensive views over the surrounding vineyards. This charming hamlet comprises 6 nice apartments (and 9 double bedrooms) all of which furnished in a  …see more

from £184 / night

£1156 - £1651 / week

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from £184 / night

13

Gaiole In Chianti - 27123007 - Gaiole in Chianti farmhouse sleeps 4

Province of Siena / Gaiole in Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Beautiful stone hamlet recently restored situated in quiet and panoramic location on the Chianti Classico hills offering extensive views over the surrounding vineyards. This charming hamlet comprises 6 nice apartments (and 9 double bedrooms) all of which furnished in a  …see more

from £140 / night

£881 - £1211 / week

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from £140 / night

20

Badia Coltibuono - 82374001 - Montegrossi castle sleeps 5

Gaiole in Chianti / Montegrossi

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Badia a Coltibuono is the first wine resort in Chianti, opening it's doors to travellers and visitors who want to share a truly unique experience. Here it is possible to encounter the magic of a venue, to observe the slow yet intense rhythm of a 1000 year old abbey and  …see more

from £246 / night

£1572 - £1833 / week

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from £246 / night

15

Gaiole In Chianti - 27123004 - Gaiole in Chianti farmhouse sleeps 4

Province of Siena / Gaiole in Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Beautiful stone hamlet recently restored situated in quiet and panoramic location on the Chianti Classico hills offering extensive views over the surrounding vineyards. This charming hamlet comprises 6 nice apartments (and 9 double bedrooms) all of which furnished in a  …see more

from £140 / night

£881 - £1211 / week

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from £140 / night

16

Selvole - 34326001 - Gaiole in Chianti farmhouse sleeps 6

Province of Siena / Gaiole in Chianti

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about pets
  • Private garden
This very special property is located on the edge of Castello di San Donato in Perano (Chianti), a beautiful hamlet which has recently been restored to such a high standard that it was awarded by the International Property Awards 2006. Cavalcanti’s position allo  …see more

from £358 / night

£2500 - £3923 / week

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from £358 / night

11

Gaiole In Chianti - 27123001 - Gaiole in Chianti farmhouse sleeps 6

Province of Siena / Gaiole in Chianti

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Beautiful stone hamlet recently restored situated in quiet and panoramic location on the Chianti Classico hills offering extensive views over the surrounding vineyards. This charming hamlet comprises 6 nice apartments (and 9 double bedrooms) all of which furnished in a  …see more

from £184 / night

£1156 - £1651 / week

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from £184 / night

Top Destination reviews

A HOLIDAY IN THE HEART OF CHIANTI
Authentic unspoiled Italian charm!

My family and I stayed at this beautiful property and had a relaxed and wonderful holiday. Gaiole in Chianti is a small village totally unspoilt by tourism and the location of this property is ideal if you hire a car and travel to all the surrounding … see more
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
Villa Podere Earthly
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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