Holiday houses in Chianti & holiday apartments in Chianti

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Experience quintessential Italy with a holiday home in Chianti

From a romantic holiday apartment on the cobbled streets of a medieval village, to a rustic rural holiday home surrounded by green meadows and centuries-old farmhouses, there are holiday rentals to suit every taste in beautiful Chianti. This region of Tuscany, between Florence and Siena, is quintessentially Italian: lush rolling hills, dotted with vineyards, interrupted by picturesque stone villages that perch impossibly on hilltops. Above all, it is known for its traditional wineries, producing some of the world's best-loved red wines.

World-class wine and tasty tours

Wine tasting in Chianti is simple to organise and rewarding. Countless vineyards offering informative tastings are crammed into this comparatively small region, making it feasible to visit several in just one day from a holiday house based anywhere in Chianti. Rent a car and set out from your holiday apartment with absolute freedom to explore secluded farmhouses and out-of-the-way cellars throughout Barberino Val d'Elsa, unearthing exquisite wines and superb food, including Chianti's prized olives. Chianti's wine is hard to stop sipping, so those visitors that would prefer not to drive can take part in all-inclusive tours covering multiple wineries and leisurely lunches. Many of the region's vineyards are accessible by public transport from your holiday rental, including Castelo Vicchiomaggio, a winery surrounding an impressive medieval castle.

Holiday houses in hilltop towns: beautiful landscapes meet rich culture

Book a holiday rental in Chianti - in the heart of Italy - and feel history around every corner. Romantic old towns dot the landscape: Montefioralle, a few miles from Greve in Chianti, still has its fortified walls to keep out invading armies, while Giaole in Chianti is a rustic town with gorgeous old buildings and winding alleys - an idyllic visual counterpart to the rolling, sun-drenched hills that fade into the distance. For families with kids, the region also offers endless hiking and biking trails. Rent a holiday home in a romantic Tuscan town or a holiday house in the countryside, and Chianti's superb landscapes, wine and heritage will take care of the rest.

Reviews from our customers

4.4 out of 5 (657 Customer reviews)
1 The holiday homes and apartments in in Chianti have been rated by 657 customers, scoring 4.4 out of 5 houses, on average.

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  • Property no. 842042
    from GBP 854
    for 1 week

    Tavernelle Val di Pesa, Chianti

    Holiday home for max. 8 persons

    Approx. 160 m², 4 bedrooms, 3 bathrooms, pets are allowed (max. 2), satellite TV, WLAN, washing machine, dishwasher, sea approx. 90 km,
    4.2 out of 5
    6 Customer reviews
  • Property no. 638076
    from GBP 469
    for 1 week

    Gaiole in Chianti, Chianti

    Holiday apartment for max. 5 persons

    Approx. 70 m², 2 bedrooms, 1 bathroom, pets are allowed (on request), satellite TV, Internet, washing machine, ,
    4.3 out of 5
    7 Customer reviews
    There is one further property type with one accommodation for this complex
  • Property no. 369126
    from GBP 259
    for 1 week

    Tavernelle Val di Pesa, Chianti

    Holiday apartment for max. 2 persons

    Approx. 37 m², 1 bedroom, 1 bathroom, pets are allowed (max. 1), satellite TV, WLAN
    5.0 out of 5
    5 Customer reviews
    There are 2 further property types with 2 accommodations for this complex
  • Property no. 913026
    from GBP 1,090
    for 1 week

    Greve in Chianti, Chianti

    Holiday home for max. 10 persons

    5 bedrooms, 2 bathrooms, pets are allowed (max. 1), satellite TV, washing machine, dishwasher,
  • Property no. 673587
    from GBP 360
    for 1 week

    Barberino Val d'Elsa, Chianti

    Holiday apartment for max. 3 adults + 2 children

    Approx. 50 m², 2 bedrooms, 1 bathroom, pets are allowed (on request), satellite TV, sea approx. 100 km,
    4.9 out of 5
    10 Customer reviews
    There is one further property type with one accommodation for this complex
  • Property no. 337412
    from GBP 428
    for 1 week

    Montevarchi, Chianti

    Holiday home for max. 8 persons

    Approx. 130 m², 4 bedrooms, 2 bathrooms, pets are allowed (max. 2), satellite TV, Internet, washing machine, dishwasher,
    4.8 out of 5
    11 Customer reviews
  • Property no. 1140305
    from GBP 638
    for 1 week

    Pergine Valdarno, Chianti

    Holiday apartment for max. 6 persons

    Approx. 130 m², 3 bedrooms, 3 bathrooms, pets are allowed (on request), satellite TV, WLAN, washing machine, dishwasher, sea approx. 112 km,
  • Property no. 1140306
    from GBP 638
    for 1 week

    Pergine Valdarno, Chianti

    Holiday apartment for max. 6 persons

    Approx. 80 m², 3 bedrooms, 2 bathrooms, pets are allowed (on request), satellite TV, WLAN, washing machine, dishwasher, sea approx. 112 km,
  • Property no. 926429
    from GBP 1,951
    for 1 week

    Sant'Appiano, Chianti

    Holiday home for max. 18 persons

    8 bedrooms, 6 bathrooms, pets are allowed (max. 1), satellite TV, washing machine, dishwasher,
  • Property no. 1148481
    from GBP 8,636
    for 1 week

    Greve in Chianti, Chianti

    Holiday home for max. 18 persons

    9 bedrooms, 9 bathrooms, pets not allowed, satellite TV, washing machine, dishwasher, non-smoking property, ,
  • Property no. 711849
    from GBP 346
    for 1 week

    Greve in Chianti, Chianti

    Holiday apartment for max. 4 persons

    Approx. 100 m², 2 bedrooms, 1 bathroom, pets not allowed, TV, Internet, washing machine, sandy beach approx. 126 km
    5.0 out of 5
    1 Customer review
  • Property no. 833092
    from GBP 519
    for 1 week

    Monteriggioni, Chianti

    Holiday apartment for max. 4 persons

    Approx. 110 m², 2 bedrooms, 2 bathrooms, pets not allowed, satellite TV, WLAN, washing machine, sea approx. 95 km, ,
    There are 2 further property types with 2 accommodations for this complex
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