Top Holiday rentals in Castellina in Chianti

Find the Top Holiday rentals in Castellina in Chianti – 10+ Quality Options from Leading Providers

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22 Guests, 1 Room
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1-10 out of 10 holiday rentals
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Farm stay
8.4
Great54 reviews
2 adults
1 bedroom
2 beds
MapView on map3.6 km from City Centre
From   US$ 394 /nightSelect
  • Restored 11th-century medieval castle
  • Seasonal outdoor pool with stunning views
  • On-site restaurant serving traditional Tuscan dishes
8.6
Great110 reviews
4 adults
1 bedroom
2 beds
MapView on map4.3 km from City Centre
From   US$ 348 /nightSelect
  • Guided wine cellar tours available
  • Traditional Tuscan cuisine restaurant
  • Elegant rooms in separate buildings
8.2
Great52 reviews
  • Outdoor pool
  • Wine bar
  • Cooking classes
4.3 km from City Centre
From   US$ 259 /nightSelect
  • 15th-century restored apartments
  • On-site wine tasting sessions
  • Saltwater seasonal pool
8.4
Great90 reviews
  • Gourmet Restaurant
  • Swimming Pool
  • Spa Services
5.1 km from City Centre
From   US$ 282 /nightSelect
  • Scenic main pool overlooking the valley
  • Gourmet restaurant with local cuisine
  • On-site yoga classes available
8.4
Great127 reviews
  • Panoramic pool
  • Tennis court
  • Restaurant
1.1 km from City Centre1.1 km from Castellina in Chianti
From   US$ 157 /nightSelect
  • Tuscan cuisine from local ingredients
  • Panoramic swimming pool with vineyard views
  • Tennis court in a serene garden
8.2
Great152 reviews
  • Infinity pool
  • Outdoor dining
  • Wine tastings
From   US$ 177 /nightSelect
  • Carefully renovated medieval village ambiance
  • Panoramic barbecue area with stunning views
  • Infinity pool overlooking Tuscan vineyards
Farm stay
8.8
Great98 reviews
  • Outdoor pool
  • Organic restaurant
  • Bicycle rental
3.2 km from City Centre
From   US$ 517 /nightSelect
  • Organic Tuscan cuisine using local ingredients
  • Private swimming pool with countryside views
  • Idyllic setting among Chianti's rolling hills
8.4
Great90 reviews
  • Infinity pool
  • On-site spa
  • Bicycle rental
7.0 km from City Centre
From   US$ 156 /nightSelect
  • Wine tasting on-site
  • Infinity pool with stunning views
  • Historic former monastery setting
Country house
8.8
Great21 reviews
  • Outdoor pool
  • Barbecue area
  • Picnic space
1.6 km from City Centre1.6 km from Castellina in Chianti
From   US$ 155 /nightSelect
  • Outdoor swimming pool with scenic views
  • Fully equipped kitchens in all units
  • Themed dinner nights and bike tours
Farm stay
  • Saltwater pool
  • Garden views
  • Barbecue area
4.9 km from City Centre
From   US$ 150 /nightSelect
  • Stunning mountain view terrace
  • Saltwater seasonal swimming pool
  • Outdoor dining area with barbecue