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Holiday houses in Chianti & holiday apartments in Chianti

  • Tuscany | Vacation on a country estate
    From USD 548

  • Tuscany | ​Holiday with your own pool
    From USD 548

  • Chianti | on a wine-growing estate during grape harvest
    From USD 440

  • The best properties in Italy
    From USD 280

  • Italy | That certain something
    From USD 548

  • Rome | Trip to the Eternal City
    From USD 582

  • Italy | Houses for group travel
    From USD 1,745

  • Italy | Bathing fun in the holiday park
    From USD 310

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Peaceful holiday home vacation in gorgeous Chianti

No holiday home ever totally feels like home, but you may have a hard time going home after getting a taste of Chianti. It's world-famous for its red wine, but it's the rolling landscapes, quaint villages and rich culture that truly set this area of central Italy apart. Whether you want to throw yourself into non-stop wine tours, explore some stunning countryside, hike mountains, or simply blob out with a book, a holiday apartment in Chianti will not disappoint.

You're on holiday - lap it up!

It is no secret that Chianti is home to some of Tuscany's most famous and impressive wineries, and there are too many fabulous vineyards to visit in one lifetime, let alone one holiday home getaway. However, a good way to start is placing yourself in a holiday apartment in the picturesque towns of Greve or Gaiole where you can get a little slice of local Italian life while also being surrounded by stunning landscapes and almost embarrassingly consistently good weather (hence the quality of the wine). Better yet, these two spots are great gateways to many vineyards offering tastings, tours or simply a good family meal very close to your accommodation.

Holiday homes suiting culture vultures and active holiday-makers alike

Few places manage to do both well, but Chianti really does offer something for everyone. Tuscany's good weather (though never insufferably hot) and sparsely populated, lush countryside offer many opportunities for hiking, cycling or swimming, no matter how young or old you are (or feel). With such stunning natural landscapes at hand, it may feel strange that just a short trip from your Chianti holiday home are the world-class cultural gems of Siena - especially its iconic cathedral and main square - and Florence, whose historical and artistic wealth is matched by very few cities. But that's exactly the case when you rent a holiday home or flat for you, your loved ones or a group of friends in Chianti.

Reviews from our customers

4.3 out of 5 (623 Customer reviews)
1 The holiday homes and apartments in in Chianti have been rated by 623 customers, scoring 4.3 out of 5 houses, on average.

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  • Property no. 1207742
    from USD 598
    for 1 week

    Lilliano, Chianti

    Holiday home for max. 6 persons

    Approx. 140 m², 2 bedrooms, 3 bathrooms, pets not allowed, satellite TV, WLAN, washing machine, dishwasher,
    3.0 out of 5
    2 Customer reviews
  • Property no. 357517
    from USD 447
    for 1 week

    San Casciano in Val di Pesa, Chianti

    Holiday apartment for max. 2 adults + 2 children

    Approx. 70 m², 2 bedrooms, 1 bathroom, pets not allowed, satellite TV, beach approx. 85 km,
    5.0 out of 5
    1 Customer review
  • Property no. 870960
    from USD 1,621
    for 1 week

    San Casciano in Val di Pesa, Chianti

    Holiday home for max. 12 persons

    Approx. 160 m², 4 bedrooms, 3 bathrooms, pets are allowed (max. 1), satellite TV, WLAN, washing machine, dishwasher, , ,
  • Property no. 1183717
    from USD 1,733
    for 1 week

    Ponte agli Stolli, Chianti

    Holiday home for max. 10 persons

    Approx. 250 m², 4 bedrooms, 4 bathrooms, pets not allowed, satellite TV, WLAN, washing machine, dishwasher,
  • Property no. 922150
    from USD 794
    for 1 week

    Villa a Sesta, Chianti

    Holiday apartment for max. 5 persons

    Approx. 130 m², 2 bedrooms, 1 bathroom, pets not allowed, satellite TV, WLAN, washing machine, dishwasher,
    4.6 out of 5
    5 Customer reviews
  • Property no. 1305063
    from USD 1,189
    for 1 week

    Bucine, Chianti

    Holiday home for max. 8 persons

    Approx. 160 m², 4 bedrooms, pets are allowed (max. 2), satellite TV, Internet, washing machine, dishwasher, beach approx. 124 km,
  • Property no. 433045
    + 7 more
    from USD 665
    for 1 week

    Pergine Valdarno, Chianti

    Holiday apartment for max. 4 persons

    Approx. 76 m², 2 bedrooms, 1 bathroom, pets are allowed (max. 2), satellite TV, Complete WLAN coverage, dishwasher, ,
    There are 7 further property types with 7 accommodations for this complex
    show more
  • Property no. 1170513
    from USD 668
    for 1 week

    Cortine, Chianti

    Holiday home for max. 6 persons

    Approx. 150 m², 3 bedrooms, 3 bathrooms, pets are allowed (max. 1), satellite TV, Internet, WLAN, washing machine, dishwasher,
  • Property no. 1199532
    from USD 4,473
    for 1 week

    Vertine, Chianti

    Holiday home for max. 10 persons

    Approx. 560 m², 5 bedrooms, 6 bathrooms, pets not allowed, satellite TV, WLAN, washing machine, dishwasher, non-smoking property, ,
  • Property no. 1305064
    from USD 561
    for 1 week

    Bucine, Chianti

    Holiday home for max. 2 persons

    Approx. 50 m², 1 bedroom, pets are allowed (max. 2), satellite TV, Internet, dishwasher, beach approx. 124 km,
  • Property no. 1305065
    from USD 772
    for 1 week

    Bucine, Chianti

    Holiday home for max. 5 persons

    Approx. 81 m², 2 bedrooms, pets are allowed (max. 2), satellite TV, Internet, dishwasher, beach approx. 124 km,
  • Property no. 1305066
    from USD 616
    for 1 week

    Bucine, Chianti

    Holiday home for max. 4 persons

    Approx. 65 m², 2 bedrooms, pets are allowed (max. 2), satellite TV, Internet, dishwasher, beach approx. 124 km,
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