Top Holiday rentals in Chianti

Find the Top Holiday rentals in Chianti – 100+ Quality Options from Leading Providers

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22 Guests, 1 Room
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1-20 out of 156 holiday rentals
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4 adults
1 bedroom
3 beds
From   US$ 124 /nightSelect
  • Bicycle rental for exploring countryside
  • Picnic area surrounded by beautiful gardens
  • Buffet or continental breakfast available
4 adults
1 bedroom
3 beds
From   US$ 248 /nightSelect
  • 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 /nightSelect
  • Historic vineyard experience since 1256
  • Outdoor baths and stunning garden views
  • On-site yoga and fitness classes offered
  • Organic farm
  • Wine cellar
  • Cooking classes
From   US$ 634 /nightSelect
  • 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 /nightSelect
  • Historic castle with wine production
  • Ancient farmhouses restored with care
  • Cooking classes with local cuisine
  • Wine cellar
  • Tuscan restaurant
  • Bicycle rental
From   US$ 276 /nightSelect
  • Guided wine cellar tours available
  • Traditional Tuscan cuisine restaurant
  • Elegant rooms in separate buildings
Farm stay
  • Outdoor pool
  • Restaurant
  • Bicycle rental
From   US$ 394 /nightSelect
  • 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 /nightSelect
  • Gourmet Tuscan cuisine with seasonal flavors
  • Scenic outdoor terrace and winter garden
  • Family-friendly with children's playground
  • Panoramic pools
  • Wine shop
  • Lounge bar
From   US$ 356 /nightSelect
  • Breathtaking views of Chianti hills
  • Exclusive D'Wine Club access
  • Tuscan cuisine with fresh local ingredients
  • Outdoor Pool
  • Barbecue Facilities
  • Concierge Service
From   US$ 181 /nightSelect
  • Seasonal outdoor swimming pool
  • Pet-friendly accommodations available
  • Daily continental breakfast options
Country house
  • Outdoor Pool
  • Tennis Courts
  • Cooking Classes
From   US$ 251 /nightSelect
  • Historic venue with ancient charm
  • Gourmet dining in historic halls
  • Beautiful gardens and terraces
  • Outdoor pool
  • Private villas
  • On-site spa
From   US$ 280 /nightSelect
  • 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 /nightSelect
  • 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 /nightSelect
  • Authentic Florentine castle experience
  • Stunning Tuscan garden views
  • Ideal romantic wedding venue
  • Salt-water pool
  • Cooking classes
  • Bicycle rental
From   US$ 380 /nightSelect
  • Organic Chianti Classico wine production
  • Panoramic views of Tuscan vineyards
  • Outdoor salt-water swimming pool
  • Infinity pool
  • On-site spa
  • Bicycle rental
From   US$ 156 /nightSelect
  • 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 /nightSelect
  • Organic extra virgin olive oil production
  • Panoramic infinity hydro-massage pool
  • Authentic Tuscan cooking classes
  • Infinity Pool
  • Wine Tastings
  • Outdoor Gardens
From   US$ 114 /nightSelect
  • Private Chianti wine tastings available
  • On-site olive oil production
  • Infinity pool overlooking Chianti hills
  • Private pool
  • Italian breakfast
  • Outdoor garden
From   US$ 113 /nightSelect
  • Private pool with beautiful garden views
  • Italian breakfast with local ingredients
  • Seasonal outdoor swimming pool
  • Outdoor pool
  • On-site restaurant
  • Wellness spa
From   US$ 506 /nightSelect
  • Organic farm with fresh produce
  • Elegant rooms with historical design
  • Tranquil views of Tuscan landscapes