Top Holiday homes in Chianti
Find the Top Holiday homes in Chianti – 70+ Quality Options from Leading Providers
41-60 out of 74 holiday homes
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9 adults
4 bedrooms
5 beds
From
US$ 505
/night
- Authentic Florentine castle experience
- Stunning Tuscan garden views
- Ideal romantic wedding venue
Country house
4 adults
2 bedrooms
2 beds
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
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
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
- Swimming Pool
- On-site Restaurant
- Free Shuttle
From
US$ 144
/night
- Outdoor swimming pool with sun loungers
- On-site restaurant with buffet options
- Free shuttle service for guests
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
- Kids' Pool
- Open-air Bath
- Bicycle Rental
From
US$ 168
/night
- Wellness packages for rejuvenation
- Family-friendly with kids' pool
- Outdoor dining area with scenic views
Farm stay
- Bicycle Rental
- Picnic Area
- Air Conditioning
From
US$ 137
/night
- Bicycle rental and guided bike tours
- Relaxing picnic area with garden views
- Accessible rooms with soundproofing
Farm stay
- Outdoor pool
- Barbecue area
- Private terrace
From
US$ 137
/night
- Pool with stunning mountain views
- Family-friendly with outdoor activities
- Facilities for disabled guests available
Country house
- Infinity pool
- Outdoor terrace
- Tuscan cuisine
From
US$ 189
/night
- Infinity pool with stunning Siena views
- Historic 18th-century restored farmhouse
- Locally sourced breakfast with homemade jams
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
- Outdoor pool
- Organic restaurant
- Bicycle rental
From
US$ 517
/night
- Organic Tuscan cuisine using local ingredients
- Private swimming pool with countryside views
- Idyllic setting among Chianti's rolling hills
Country house
- Outdoor pool
- Bicycle rentals
- Large garden
From
US$ 162
/night
- Colonial house with Tuscan architecture
- Large garden with outdoor pool
- Free parking and bicycle rentals
Country house
- Saltwater pool
- In-house restaurant
- Tennis court
From
US$ 351
/night
- Saltwater seasonal outdoor pool
- In-house traditional restaurant
- Billiards and tennis facilities
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 pool
- Restaurant
- Children's play area
From
US$ 278
/night
- Traditional Italian restaurant with diverse menus
- Outdoor swimming pool with scenic views
- Activities like cooking classes and hiking
Farm stay
- Outdoor pool
- BBQ facilities
- Bicycle rental
From
US$ 449
/night
- Outdoor seasonal pool with stunning views
- Self-catering apartments with private balconies
- Activities like cycling and hiking available
Country house
- Winter Garden
- Children's Playground
- Panoramic Terrace
From
US$ 190
/night
- Gourmet Tuscan cuisine with seasonal flavors
- Scenic outdoor terrace and winter garden
- Family-friendly with children's playground
Country house
- Mediterranean Garden
- Swimming Pool
- Boutique Accommodations
From
US$ 183
/night
- 14th-century restored watermill hotel
- Extensive Mediterranean garden with pool
- Daily buffet breakfast with local products
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