Top Holiday homes in Chianti
Find the Top Holiday homes in Chianti – 100+ Quality Options from Leading Providers
21-40 out of 114 holiday homes
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Farm stay
15 adults
8 bedrooms
8 beds
From
US$ 162
/night
- Restored ancient farmhouses with vineyard views
- Two outdoor pools surrounded by nature
- Cooking classes focusing on Tuscan cuisine
Farm stay
6 adults
2 bedrooms
3 beds
From
US$ 344
/night
- Historic former convent accommodations
- Extensive wine tour and tasting experiences
- Outdoor swimming pools with stunning views
Country house
- Cooking school
- Infinity pool
- Wellness spa
From
US$ 369
/night
- Tuscan cooking classes with local ingredients
- Infinity pool overlooking Antinori vineyards
- Wellness spa with sauna and hammam
Farm stay
- Infinity pool
- On-site restaurant
- Wellness spa
From
US$ 274
/night
- Traditional Tuscan cuisine with own wines
- Infinity pool with panoramic views
- Spa with Turkish bath and massages
Country house
- Saltwater pool
- In-house restaurant
- Tennis court
From
US$ 351
/night
- Saltwater seasonal outdoor pool
- In-house traditional restaurant
- Billiards and tennis facilities
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
- 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
Country house
- Infinity pool
- Outdoor terrace
- Tuscan cuisine
From
US$ 189
/night
- Infinity pool with stunning Siena views
- Historic 18th-century restored farmhouse
- Locally sourced breakfast with homemade jams
Farm stay
- Outdoor pool
- On-site restaurant
- Wine cellar
From
US$ 247
/night
- Charming villa with historic features
- On-site wine production and tasting tours
- Contemporary cuisine at Osteria 1126
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
- Outdoor Pool
- Traditional Restaurant
- Bicycle Rental
From
US$ 165
/night
- Tuscan cuisine with local wines
- Outdoor pool with vineyard views
- Bicycle rental for exploring surroundings
Farm stay
- Infinity pool
- Bicycle rental
- Outdoor spa
From
US$ 154
/night
- Infinity pool with stunning views
- Family-friendly activities on-site
- Local cuisine breakfast options available
Country house
- Private Forest
- Cooking Workshops
- Open-Air Spa
From
US$ 165
/night
- 12th-century historical residence
- Medieval village atmosphere
- Tuscan cooking workshops available
Country house
- Outdoor pool
- Private villa
- Traditional restaurant
From
US$ 160
/night
- Historic castle with wine production
- Ancient farmhouses restored with care
- Cooking classes with local cuisine
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
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
Country house
- Outdoor pool
- On-site spa
- Family activities
From
US$ 368
/night
- 17th-century renovated farmhouse charm
- Surrounded by vineyards and olive groves
- Outdoor swimming pool with scenic views
Farm stay
- Outdoor pool
- On-site restaurant
- Pet-friendly
From
US$ 300
/night
- Farm-to-table Tuscan dining experiences
- Wine and olive oil production on-site
- Rustic-chic wedding venue options
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
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
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