Top Holiday homes in Chianti
Find the Top Holiday homes in Chianti – 100+ Quality Options from Leading Providers
1-20 out of 114 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
Country house
6 adults
3 bedrooms
3 beds
From
US$ 215
/night
- Historic vineyard experience since 1256
- Outdoor baths and stunning garden views
- On-site yoga and fitness classes offered
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
Country house
- Organic farm
- Wine cellar
- Cooking classes
From
US$ 545
/night
- Historic abbey with thousand-year-old charm
- Authentic Tuscan cooking classes available
- Stunning Italian gardens for relaxation
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
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
- Infinity pool
- Traditional restaurant
- Cooking classes
From
US$ 248
/night
- Historic castle with wine production
- Elegant rooms with classic style
- Infinity pool with valley views
Farm stay
- Salt-water pool
- Cooking classes
- Bicycle rental
From
US$ 380
/night
- Organic Chianti Classico wine production
- Panoramic views of Tuscan vineyards
- Outdoor salt-water swimming pool
- 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
- Outdoor Pool
- Tennis Courts
- Cooking Classes
From
US$ 251
/night
- Historic venue with ancient charm
- Gourmet dining in historic halls
- Beautiful gardens and terraces
Farm stay
- Infinity Pool
- Tasting Room
- Private Church
From
US$ 515
/night
- Vineyard-overlook rooms with medieval style
- Private wine tasting experiences available
- Infinity pool with stunning countryside 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
- Infinity Pool
- Wine Tastings
- Outdoor Gardens
From
US$ 114
/night
- Private Chianti wine tastings available
- On-site olive oil production
- Infinity pool overlooking Chianti hills
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
- Wellness spa
- Tuscan-style rooms
From
US$ 248
/night
- Medieval castle charm and comfort
- Wellness spa with massages available
- Outdoor pool with panoramic views
Farm stay
- Heated pool
- Cooking classes
- Bicycle rental
From
US$ 289
/night
- Award-winning winery tours available
- Renovated medieval country estate
- Private garden villas for couples
Farm stay
- Outdoor pool
- Wine bar
- Cooking classes
From
US$ 259
/night
- 15th-century restored apartments
- On-site wine tasting sessions
- Saltwater seasonal pool
Farm stay
- Restaurant
- Seasonal Pool
- Bicycle Rentals
From
US$ 308
/night
- Seasonal outdoor pool with views
- Restaurant serving local Italian cuisine
- Bicycle rental and bike tours available
Farm stay
- Outdoor pool
- Private gardens
- Cooking lessons
From
US$ 272
/night
- Surrounded by vineyards and olive groves
- Organic garden with fresh vegetables
- Family-friendly amenities and services
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