Top Holiday rentals in Chianti
Find the Top Holiday rentals in Chianti – 100+ Quality Options from Leading Providers
1-20 out of 156 holiday rentals
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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
Country house
- Outdoor pools
- Picnic area
- Fitness club
From
US$ 215
/night
- Historic vineyard experience since 1256
- Outdoor baths and stunning garden views
- On-site yoga and fitness classes offered
Country house
- Organic farm
- Wine cellar
- Cooking classes
From
US$ 634
/night
- Historic abbey with thousand-year-old charm
- Authentic Tuscan cooking classes available
- Stunning Italian gardens for relaxation
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
Country house
- Wine cellar
- Tuscan restaurant
- Bicycle rental
From
US$ 276
/night
- Guided wine cellar tours available
- Traditional Tuscan cuisine restaurant
- Elegant rooms in separate buildings
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
- Winter Garden
- Children's Playground
- Panoramic Terrace
From
US$ 207
/night
- Gourmet Tuscan cuisine with seasonal flavors
- Scenic outdoor terrace and winter garden
- Family-friendly with children's playground
Country house
- Panoramic pools
- Wine shop
- Lounge bar
From
US$ 356
/night
- Breathtaking views of Chianti hills
- Exclusive D'Wine Club access
- Tuscan cuisine with fresh local ingredients
Country house
- Outdoor Pool
- Barbecue Facilities
- Concierge Service
From
US$ 181
/night
- Seasonal outdoor swimming pool
- Pet-friendly accommodations available
- Daily continental breakfast options
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
- Outdoor pool
- Private villas
- On-site spa
From
US$ 280
/night
- Historic 11th century Medici villa
- Organic wine and olive oil production
- Wellness packages with spa treatments
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
- Outdoor pool
- Historic apartments
- On-site restaurant
From
US$ 505
/night
- Authentic Florentine castle experience
- Stunning Tuscan garden views
- Ideal romantic wedding venue
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
Farm stay
- Infinity pool
- On-site spa
- Bicycle rental
From
US$ 156
/night
- Wine tasting on-site
- Infinity pool with stunning views
- Historic former monastery setting
Farm stay
- Infinity pool
- Cooking class
- On-site restaurant
From
US$ 279
/night
- Organic extra virgin olive oil production
- Panoramic infinity hydro-massage pool
- Authentic Tuscan cooking classes
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
- Private pool
- Italian breakfast
- Outdoor garden
From
US$ 113
/night
- Private pool with beautiful garden views
- Italian breakfast with local ingredients
- Seasonal outdoor swimming pool
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
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