Holiday castles in Province of Siena

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11 Holiday homes

Filters applied: Castle (11)

16

Luxury Chianti apartment with shared pool, private garden, barbecue - Castellina In Chianti castle sleeps 4

Province of Siena / Castellina In Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
Come to the heart of the Chianti region to discover a wonderfully charming inn and agritourism facility that offers hotel-like amenities in elegant apartment suites, set in the evocative atmosphere of the Tuscan hills. Resting on a rolling hill, the Borgo is located  …see more

from £137 / night

£954 - £1322 / week

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from £137 / 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

26

Enchanting Winery - Poggibonsi castle sleeps 14

Province of Siena / Poggibonsi

5 14 7 nights min

  • 5 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Enchanting Winery At the top of a hill with 309 hectares between wood, olive trees and wine yards is located this enchanting winery, with it’s amazing medioeval castle, the pool villa, the farmhouse and a real good Chianti wine production. This property is the cherry  …see more

from £407 / night

£2845 - £4173 / week

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from £407 / night

(1) Good 

24

Province of Siena / Poggibonsi

7 12 3 nights min

  • 7 bedrooms
  • Sleeps 12
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

 …see more

from £432 / night

£3018 / week

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from £432 / night

33

Castello Montelifré - San Giovanni d'Asso castle sleeps 9

Province of Siena / San Giovanni d'Asso

4 9 3 nights min

  • 4 bedrooms
  • Sleeps 9
  • 3 nights min
  • Child friendly
  • Ask about pets
  • Private garden
Welcome at Montelifrè's castle Montelifrè is a medieval village still owned by the ancient and noble family Martinozzi.The hamlet is one of the oldest military buildings in Crete senesi and Valdorcia, in Tuscany, one ofthe most beautiful italian regions. Montelifrè i  …see more

from £39 / night

£173 - £2104 / week

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from £39 / night

23

Badia Coltibuono - 82374005 - Montegrossi castle sleeps 3

Gaiole in Chianti / Montegrossi

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
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 £150 / night

£1005 - £1180 / week

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from £150 / 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

17

Badia Coltibuono - 82374002 - Montegrossi castle sleeps 5

Gaiole in Chianti / Montegrossi

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
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 £193 / night

£1180 - £1400 / week

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from £193 / night

20

Badia Coltibuono - 82374004 - Montegrossi castle sleeps 7

Gaiole in Chianti / Montegrossi

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
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 £228 / night

£1443 - £1706 / week

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from £228 / night

20

Badia Coltibuono - 82374003 - Montegrossi castle sleeps 6

Gaiole in Chianti / Montegrossi

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
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

9

Province of Siena / Castelnuovo Berardenga

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £156 / night

£1087 / week

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from £156 / 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
Villa Vianci
Best vacation ever!

Our entire experience at Villa Vianci was beyond expectations. We travelled with 4 generations, ages 3 1/2 to 85! The villa was spectacular, spacious & immaculate. The pictures on line don't do it justice. Tommasso & Chiara were the best, any que … see more
Podere Val delle Corti
Very nice and total clean appartment

Beautiful property within a lovely environment Very nice and total clean appartment Landlady and the whole proprietor familiy are very friendly an helpful No kind of weakness has been discovered, at all … see more
La Casina Toscana, central with parking and wi-fi
Clean, comfortable and cozy house with privacy and convenience to Montepuciano

We had a very enjoyable stay at Davide's house. It is a truly charming place offering the privacy you need as a family and at the same time the convenience of being close enough to walk to the Montepulciano town. The place was very clean and thoughtf … see more
Agriturismo Sammonti
Perfect week in Tuscany

All previous positive reviews reflect our experience. Beautiful, quiet location. Lovely hosts. The house was cosy and a great place to come home to after sightseeing. It was also very easy to spend a whole day in the local area or enjoying the pool … see more
Villa Galardini
Great location in heart of Tuscany; wonderful property and very friendly owners

Property is peaceful, clean and ideally located for daytrips to the many nearby villages and Sienna. Grocery stores and restaurants conveniently located in nearby Buonconvento . This was a 50th Birthday celebration vacation to Tuscany with spouse a … see more

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