Top Holiday homes in Chianti
Find the Top Holiday homes in Chianti – 100+ Quality Options from Leading Providers
41-60 out of 114 holiday homes
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Farm stay
6 adults
3 bedrooms
4 beds
From
US$ 127
/night
- Elegant apartments in Tuscan style
- Outdoor pools with vineyard views
- Traditional Tuscan dining experience
Country house
2 adults
1 bedroom
1 bed
From
US$ 288
/night
- Panoramic outdoor swimming pool
- Tuscan-style air-conditioned rooms
- Wine tasting tours available
Country house
- Outdoor Pool
- Hot Tub
- Cooking Classes
From
US$ 315
/night
- Outdoor pool with Brolio Castle views
- Rustic rooms with cozy fireplaces
- All-year-round hot tub with music
Country house
- Outdoor pool
- Family rooms
- Private terrace
From
US$ 114
/night
- Year-round outdoor swimming pool
- Family-friendly outdoor play area
- Italian breakfast with fresh pastries
Farm stay
- Panoramic Pool
- Cooking Lessons
- eBike Rental
From
US$ 230
/night
- Tuscan cooking lessons with local chef
- Panoramic swimming pool with stunning views
- Elegant rooms with handcrafted furniture
Country house
- Outdoor pool
- Garden
- Bar area
From
US$ 143
/night
- Historic estate dating back to the 1400s
- Outdoor swimming pool with sun loungers
- Dining on terrace with scenic views
Country house
- Outdoor Pool
- Cooking Classes
- Bike Tours
From
US$ 187
/night
- Outdoor pool with stunning views
- Cooking classes for culinary enthusiasts
- All ages welcome at outdoor pool
Country house
- Outdoor Pool
- Family Rooms
- Pet Friendly
From
US$ 276
/night
- Saltwater pool with scenic views
- Family-friendly restaurant with Italian cuisine
- Cooking classes for all ages
Country house
- Outdoor pool
- Garden
- Spa services
From
US$ 142
/night
- Outdoor swimming pool with views
- Rustic-style rooms with garden access
- On-site spa services available
Farm stay
- Outdoor Pool
- Garden Terrace
- Bike Rentals
From
US$ 137
/night
- Vineyard tours and wine tastings
- Olive oil and saffron production
- Seasonal saltwater pool
Farm stay
- Outdoor pool
- BBQ facilities
- Garden views
From
US$ 977
/night
- Yoga classes and outdoor spaces
- Scenic pool with view
- Facilities for disabled guests
- Outdoor Pool
- Picnic Area
- Air Conditioning
From
US$ 167
/night
- Historic building with beautiful vineyard views
- Scenic outdoor picnic and garden area
- Seasonal outdoor pool with sun loungers
Farm stay
- Infinity pool
- Organic vineyards
- Playground
From
US$ 400
/night
- Infinity pool with stunning valley views
- Organic wine tasting experiences available
- Family-friendly with playground and pet-friendly
Country house
- Outdoor pool
- Bicycle rental
- Private garden
From
US$ 107
/night
- Rustic-style rooms with private patios
- Expansive gardens and olive groves
- Outdoor swimming pool with scenic views
Farm stay
- Infinity Pool
- Organic Farm
- Cooking Classes
From
US$ 185
/night
- Organic farm with wine and olive oil
- Infinity pool with vineyard views
- Authentic Tuscan cooking classes
Country house
- Panoramic pool
- Tennis court
- Restaurant
From
US$ 157
/night
- Tuscan cuisine from local ingredients
- Panoramic swimming pool with vineyard views
- Tennis court in a serene garden
Farm stay
- Outdoor fireplace
- Barbecue facilities
- Coffee shop
From
US$ 156
/night
- On-site vineyard and wine tasting
- Seasonal outdoor pool with mountain views
- Tennis court and bike rentals available
Farm stay
- Outdoor Pool
- Farm Produce
- Historic Accommodations
From
US$ 295
/night
- Historic farm producing local wines and olive oil
- Surrounded by forests and vineyards
- Seasonal outdoor swimming pool
Farm stay
- Outdoor Pool
- On-site Restaurant
- Large Garden
From
US$ 243
/night
- Traditional Tuscan farmhouse experience
- Panoramic views of medieval towers
- On-site restaurant serving Tuscan dishes
Country house
- Swimming Pool
- Spacious Gardens
- Comfortable Rooms
From
US$ 86
/night
- Beautiful views of Chianti Hills
- Surrounded by large park with wildlife
- Seasonal outdoor swimming pool
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