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Holiday houses in Chianti & holiday apartments in Chianti

  • Tuscany | Vacation on a country estate
    From USD 458

  • Tuscany | ​Holiday with your own pool
    From USD 559

  • 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 392

  • Rome | Trip to the Eternal City
    From USD 464

  • Italy | Houses for group travel
    From USD 2,329

  • Italy | Bathing fun in the holiday park
    From USD 308

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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

4.4 out of 5 (673 Customer reviews)
1 The holiday homes and apartments in in Chianti have been rated by 673 customers, scoring 4.4 out of 5 houses, on average.

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  • Property no. 644384
    + 5 more
    from USD 704
    for 1 week

    San Donato in Poggio, Chianti

    Holiday apartment for max. 4 persons

    Approx. 55 m², 2 bedrooms, 1 bathroom, pets not allowed, satellite TV, Complete WLAN coverage, dishwasher, sea approx. 90 km,
    5.0 out of 5
    1 Customer review
    There are 5 further property types with 5 accommodations for this complex
    show more
  • Property no. 1225854
    from USD 3,340
    for 1 week

    Radda in Chianti, Chianti

    Holiday home for max. 12 persons

    6 bedrooms, 6 bathrooms, pets not allowed, satellite TV, washing machine, dishwasher, ,
  • Property no. 838417
    from USD 559
    for 1 week

    Monsanto, Chianti

    Holiday apartment for max. 5 persons

    Approx. 110 m², 2 bedrooms, 2 bathrooms, pets are allowed (max. 1), satellite TV, washing machine, dishwasher, non-smoking property,
  • Property no. 858409
    from USD 4,030
    for 1 week

    Volpaia, Chianti

    Holiday home for max. 14 persons

    Approx. 400 m², 6 bedrooms, 6 bathrooms, pets are allowed (max. 1), satellite TV, WLAN, washing machine, dishwasher,
  • Property no. 853755
    + 2 more
    from USD 1,442
    for 1 week

    Madonna di Pietracupa, Chianti

    Holiday apartment for max. 8 persons

    Approx. 180 m², 3 bedrooms, 3 bathrooms, pets are allowed (max. 1), WLAN, washing machine,
    4.0 out of 5
    2 Customer reviews
    There are 2 further property types with 2 accommodations for this complex
  • Property no. 922150
    from USD 793
    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. 944374
    from USD 2,271
    for 1 week

    Prumiano, Chianti

    Holiday home for max. 14 persons

    7 bedrooms, 5 bathrooms, pets are allowed (max. 1), satellite TV, washing machine, dishwasher, non-smoking property, ,
  • Property no. 1017334
    from USD 1,616
    for 1 week

    Ponte agli Stolli, Chianti

    Holiday home for max. 10 persons

    Approx. 200 m², 4 bedrooms, 3 bathrooms, pets not allowed, TV, Internet, washing machine, dishwasher,
  • Property no. 1307581
    from USD 2,067
    for 1 week

    Pergine Valdarno, Chianti

    Holiday home for max. 8 persons

    Approx. 240 m², 4 bedrooms, 4 bathrooms, pets are allowed (max. 2), TV, Complete WLAN coverage, washing machine, dishwasher,
  • 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. 843267
    from USD 2,207
    for 1 week

    Tignano, Chianti

    Holiday home for max. 8 persons

    Approx. 270 m², 4 bedrooms, 3 bathrooms, pets not allowed, TV, WLAN, washing machine, dishwasher,
  • Property no. 843123
    from USD 8,068
    for 1 week

    Montebenichi, Chianti

    Holiday home for max. 14 persons

    7 bedrooms, 7 bathrooms, pets not allowed, satellite TV, WLAN, washing machine, dishwasher,
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