Top Holiday homes in Chianti
Find the Top Holiday homes in Chianti – 70+ Quality Options from Leading Providers
1-20 out of 74 holiday homes
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Farm stay
4 adults
1 bedroom
3 beds
From
US$ 124
/night
- Bicycle rental for exploring countryside
- Picnic area surrounded by beautiful gardens
- Buffet or continental breakfast available
Farm stay
4 adults
1 bedroom
3 beds
From
US$ 248
/night
- Historic castle with wine production
- Elegant rooms with classic style
- Infinity pool with valley views
Farm stay
- Outdoor pool
- On-site restaurant
- Cooking class
From
US$ 220
/night
- Outdoor swimming pool with scenic views
- On-site cooking classes available
- Historic building with charm
Country house
- Panoramic pools
- Wine shop
- Lounge bar
From
US$ 973
/night
- Breathtaking views of Chianti hills
- Exclusive D'Wine Club access
- Tuscan cuisine with fresh local ingredients
- Outdoor pool
- Private villas
- On-site spa
From
US$ 252
/night
- Historic 11th century Medici villa
- Organic wine and olive oil production
- Wellness packages with spa treatments
Country house
- Wine cellar
- Tuscan restaurant
- Bicycle rental
From
US$ 348
/night
- Guided wine cellar tours available
- Traditional Tuscan cuisine restaurant
- Elegant rooms in separate buildings
Farm stay
- Organic winery
- Tuscan restaurant
- Outdoor pool
From
US$ 172
/night
- Organic wine production and tasting tours
- Tuscan restaurant with advance booking only
- Seasonal outdoor pool with panoramic views
Farm stay
- Outdoor Pool
- Massage Services
- Bicycle Rental
From
US$ 198
/night
- Tuscan-style en suite accommodation
- Outdoor pool with Tuscan countryside views
- Restaurant serving local specialties
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
Farm stay
- Infinity Pool
- Mountain Bikes
- Cooking Classes
From
US$ 314
/night
- Private cooking lessons with local chef
- Breath-taking views of San Gimignano
- Electric vehicle charging available
Farm stay
- Wine baths
- Outdoor pool
- Tennis court
From
US$ 235
/night
- Vineyard-surrounded accommodations
- Wine therapy and massages available
- Panoramic pool with vineyard views
Country house
- Outdoor Pool
- Barbecue Facilities
- Concierge Service
From
US$ 166
/night
- Seasonal outdoor swimming pool
- Pet-friendly accommodations available
- Daily continental breakfast options
Farm stay
- Outdoor pool
- Children's playground
- Picnic area
From
US$ 121
/night
- Seasonal outdoor swimming pool
- Family-friendly children's playground
- Picnic area with barbecue
Farm stay
- Infinity Pool
- Organic Farm
- Cooking Classes
From
US$ 185
/night
- Organic farm with wine and olive oil
- Infinity pool with vineyard views
- Authentic Tuscan cooking classes
Holiday home
- Private terrace
- Swimming pool
- Horse riding
From
US$ 183
/night
- Panoramic views of Siena's Duomo
- Large swimming pool with whirlpool
- Charming Tuscan-style apartments
Farm stay
- Outdoor pool
- On-site restaurant
- Wellness spa
From
US$ 506
/night
- Organic farm with fresh produce
- Elegant rooms with historical design
- Tranquil views of Tuscan landscapes
Farm stay
- Outdoor pool
- Restaurant
- Bicycle rental
From
US$ 394
/night
- Restored 11th-century medieval castle
- Seasonal outdoor pool with stunning views
- On-site restaurant serving traditional Tuscan dishes
Farm stay
- Outdoor pool
- Wine bar
- Cooking classes
From
US$ 259
/night
- 15th-century restored apartments
- On-site wine tasting sessions
- Saltwater seasonal pool
Country house
- Outdoor Pool
- Tennis Courts
- Cooking Classes
From
US$ 251
/night
- Historic venue with ancient charm
- Gourmet dining in historic halls
- Beautiful gardens and terraces
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