Top Vacation homes in Chianti

Find the Top Vacation homes in Chianti – 100+ Quality Options from Leading Providers

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Rooms & Guests
22 Guests, 1 Room
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101-120 out of 185 vacation homes
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2 adults
1 bedroom
1 bed
From   US$ 97 /nightSelect
  • Panoramic views of Chianti Hills
  • Cooking school and Tuscan meals
  • Organic farm shop with local products
5 adults
3 bedrooms
3 beds
From   US$ 116 /nightSelect
  • Self-catering apartments with rustic charm
  • Outdoor swimming pool and garden area
  • Wine and olive oil tastings available
  • Stone Villas
  • Private BBQ
  • Outdoor Play Area
From   US$ 256 /nightSelect
  • Exclusive stone swimming pool
  • Sustainable farming practices
  • Beautiful panoramic views
  • Outdoor pools
  • Tuscan restaurant
  • Wine cellar
From   US$ 127 /nightSelect
  • Traditional Tuscan brasserie restaurant
  • Two stylish outdoor swimming pools
  • Elegant apartments with rustic decor
  • Wine tastings
  • Outdoor pool
  • Horseback riding
From   US$ 250 /nightSelect
  • Medieval castle with historical charm
  • Wine tastings in Chianti vineyards
  • Outdoor swimming pool with scenic views
  • Open-air bath
  • Garden views
  • BBQ facilities
From   US$ 977 /nightSelect
  • Scenic outdoor swimming pool
  • Yoga classes in tranquil setting
  • Pet-friendly accommodations available
  • Swimming Pool
  • Playground
  • Bar Area
From   US$ 260 /nightSelect
  • Expansive gardens with swimming pool
  • Tuscan-style apartments with full kitchens
  • Homemade olive oil available for purchase
  • Outdoor Pool
  • Wine Shop
  • Restaurant
From   US$ 173 /nightSelect
  • Authentic Tuscan dining experience
  • Beautiful apartments with panoramic views
  • On-site winery for Chianti Classico
Country house
  • Outdoor Pool
  • Cooking Classes
  • Wine Tours
From   US$ 149 /nightSelect
  • Tuscan-style rooms with air conditioning
  • Outdoor swimming pool with Chianti views
  • Cooking lessons featuring Italian recipes
  • Bicycle rental
  • Picnic area
  • Private terrace
From   US$ 137 /nightSelect
  • Bicycle rental and guided bike tours
  • Outdoor dining area for picnics
  • Private terrace with garden views
Holiday home
  • Swimming Pool
  • Private Terrace
  • Mountain Biking
From   US$ 183 /nightSelect
  • Panoramic view of Siena's Duomo
  • Large swimming pool with whirlpool
  • Tuscan-style apartments with private terraces
  • Outdoor Pool
  • Wine Tasting
  • Private Gardens
From   US$ 238 /nightSelect
  • Panoramic vineyard views
  • Award-winning wine production
  • Private gardens with seating
  • Cooking School
  • Horseback Riding
  • Infinity Pool
From   US$ 154 /nightSelect
  • Tuscan cuisine with on-site wine
  • Equestrian facilities for horseback riding
  • Outdoor swimming pool with views
  • Saltwater pool
  • Organic garden
  • Self-catering cottage
From   US$ 385 /nightSelect
  • Organic olive oil and wine tasting
  • Sustainable agritourism in Tuscany
  • Cooking classes featuring local cuisine
  • Outdoor Pool
  • Yoga Classes
  • Bicycle Rental
From   US$ 1 167 /nightSelect
  • Scenic outdoor swimming pool
  • Yoga and fitness classes available
  • Packaged lunches for excursions
Holiday home
  • Infinity pool
  • Spa services
  • Cycling rentals
From   US$ 340 /nightSelect
  • Infinity pool with mountain views
  • On-site spa and wellness options
  • Barbecue facilities in the garden
Farm stay
  • Infinity pool
  • Fitness centre
  • Children's playground
From   US$ 313 /nightSelect
  • Infinity pool with scenic views
  • Family-friendly children's playground
  • On-site cooking classes available
  • Outdoor Pool
  • Restaurant
  • Cooking Classes
From   US$ 349 /nightSelect
  • Tuscan cuisine with cooking classes available
  • Country-style apartments with scenic views
  • Seasonal outdoor swimming pool for relaxation
Country house
  • Saltwater pool
  • Open-air bath
  • Relaxation room
From   US$ 103 /nightSelect
  • Saltwater pool with sunbathing area
  • Guided excursions and taxi service
  • Open-air bath for relaxation
9.6
Perfect1 review
  • Bicycle Parking
  • Picnic Area
  • Coffee Shop
From   US$ 119 /nightSelect
  • Bicycle parking and picnic area
  • On-site coffee shop and bar
  • Walking tours available