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Holiday houses in San Giorgio & holiday apartments in San Giorgio

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  • Chianti | on a wine-growing estate during grape harvest
    From GBP 359

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    From GBP 348

  • Tuscany | ​Holiday with your own pool
    From GBP 457

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    From GBP 320

  • Rome | Trip to the Eternal City
    From GBP 768

  • Italy | Houses for group travel
    From GBP 1,305

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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.

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  • Property no. 878061
    from GBP 1,749
    for 1 week

    San Giorgio, Tuscany (Chianti)

    Holiday home for max. 10 persons

    Approx. 160 m², 4 bedrooms, 4 bathrooms, pets are allowed (max. 1), satellite TV, Internet, washing machine, dishwasher, ,
  • Property no. 843180
    from GBP 4,067
    for 1 week

    San Giorgio, Tuscany (Chianti)

    Holiday home for max. 8 persons

    Approx. 300 m², 3 bedrooms, 3 bathrooms, pets not allowed, satellite TV, WLAN, washing machine, dishwasher, ,
  • Property no. 1318166
    from GBP 4,068
    for 1 week

    San Giorgio, Tuscany (Chianti)

    Holiday home for max. 8 persons

    3 bedrooms, 3 bathrooms, pets not allowed, satellite TV, washing machine, dishwasher, ,