Top Holiday homes in Chianti
Find the Top Holiday homes in Chianti – 100+ Quality Options from Leading Providers
41-60 out of 136 holiday homes
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Farm stay
4 adults
1 bedroom
2 beds
From
US$ 422
/night
- Historic winery with exclusive tastings
- Beautiful vineyard and olive grove views
- On-site restaurant with Tuscan cuisine
Farm stay
5 adults
1 bedroom
2 beds
From
US$ 198
/night
- Tuscan-style en suite accommodation
- Outdoor pool with Tuscan countryside views
- Restaurant serving local specialties
Farm stay
- Outdoor pool
- BBQ facilities
- Bicycle rental
From
US$ 449
/night
- Outdoor seasonal pool with stunning views
- Self-catering apartments with private balconies
- Activities like cycling and hiking available
Farm stay
- Organic winery
- Tuscan restaurant
- Outdoor pool
From
US$ 164
/night
- Organic wine production and tasting tours
- Tuscan restaurant with advance booking only
- Seasonal outdoor pool with panoramic views
Farm stay
- Outdoor Pool
- On-site Restaurant
- Large Garden
From
US$ 243
/night
- Traditional Tuscan farmhouse experience
- Panoramic views of medieval towers
- On-site restaurant serving Tuscan dishes
Farm stay
- Outdoor Pool
- Garden
- Spa Services
From
US$ 531
/night
- Seasonal outdoor pool with stunning views
- On-site spa offering various massages
- Garden with barbecue facilities for guests
Country house
- Outdoor pool
- Wellness spa
- Tuscan-style rooms
From
US$ 248
/night
- Medieval castle charm and comfort
- Wellness spa with massages available
- Outdoor pool with panoramic views
Country house
- Outdoor pool
- Garden
- Bar area
From
US$ 130
/night
- Historic estate dating back to the 1400s
- Outdoor swimming pool with sun loungers
- Dining on terrace with scenic views
Country house
- Infinity pool
- Outdoor jacuzzi
- Cooking class
From
US$ 288
/night
- Panoramic outdoor swimming pool
- Tuscan-style air-conditioned rooms
- Wine tasting tours available
Farm stay
- Swimming Pool
- On-site Restaurant
- Free Shuttle
From
US$ 144
/night
- Outdoor swimming pool with sun loungers
- On-site restaurant with buffet options
- Free shuttle service for guests
Farm stay
- Panoramic Pool
- Cooking Lessons
- eBike Rental
From
US$ 230
/night
- Tuscan cooking lessons with local chef
- Panoramic swimming pool with stunning views
- Elegant rooms with handcrafted furniture
Country house
- Outdoor Pool
- Family Rooms
- Pet Friendly
From
US$ 260
/night
- Saltwater pool with scenic views
- Family-friendly restaurant with Italian cuisine
- Cooking classes for all ages
Farm stay
- Outdoor Pool
- Garden Terrace
- Bike Rentals
From
US$ 137
/night
- Vineyard tours and wine tastings
- Olive oil and saffron production
- Seasonal saltwater pool
Farm stay
- Outdoor fireplace
- Barbecue facilities
- Coffee shop
From
US$ 156
/night
- On-site vineyard and wine tasting
- Seasonal outdoor pool with mountain views
- Tennis court and bike rentals available
Country house
- Outdoor Pool
- On-site Spa
- Bicycle Rental
From
US$ 138
/night
- Traditional Tuscan cuisine restaurant
- Family-run with personal service
- Surrounded by vineyards and olive groves
Country house
- Outdoor pool
- On-site spa
- Family activities
From
US$ 344
/night
- 17th-century renovated farmhouse charm
- Surrounded by vineyards and olive groves
- Outdoor swimming pool with scenic views
Farm stay
- Outdoor pool
- Restaurant
- Children's play area
From
US$ 278
/night
- Traditional Italian restaurant with diverse menus
- Outdoor swimming pool with scenic views
- Activities like cooking classes and hiking
- Outdoor Pool
- Picnic Area
- Air Conditioning
From
US$ 167
/night
- Historic building with beautiful vineyard views
- Scenic outdoor picnic and garden area
- Seasonal outdoor pool with sun loungers
Farm stay
From
US$ 23
/night
Within a 10-minute drive of Church of Santa Maria, the Agriturismo Il Colombaio B&B includes 10 rooms.
Farm stay
- Panoramic pool
- Bicycle rental
- Traditional restaurant
From
US$ 196
/night
- Panoramic pool with castle views
- Traditional Tuscan cuisine restaurant
- Free bicycle rental for exploration
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