Top Holiday homes in Chianti
Find the Top Holiday homes in Chianti – 10+ Quality Options from Leading Providers
1-19 out of 19 holiday homes
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Country house
6 adults
3 bedrooms
3 beds
From
US$ 215
/night
- Historic vineyard experience since 1256
- Outdoor baths and stunning garden views
- On-site yoga and fitness classes offered
Farm stay
9 adults
4 bedrooms
5 beds
From
US$ 259
/night
- 15th-century restored apartments
- On-site wine tasting sessions
- Saltwater seasonal pool
Farm stay
- Infinity pool
- Traditional restaurant
- Cooking classes
From
US$ 248
/night
- Historic castle with wine production
- Elegant rooms with classic style
- Infinity pool with valley views
Farm stay
- Outdoor pool
- On-site restaurant
- Cooking class
From
US$ 220
/night
- Outdoor swimming pool with scenic views
- On-site cooking classes available
- Historic building with charm
Country house
- Panoramic pools
- Wine shop
- Lounge bar
From
US$ 973
/night
- Breathtaking views of Chianti hills
- Exclusive D'Wine Club access
- Tuscan cuisine with fresh local ingredients
Farm stay
- Outdoor Pool
- Massage Services
- Bicycle Rental
From
US$ 198
/night
- Tuscan-style en suite accommodation
- Outdoor pool with Tuscan countryside views
- Restaurant serving local specialties
Country house
- Wine cellar
- Tuscan restaurant
- Bicycle rental
From
US$ 348
/night
- Guided wine cellar tours available
- Traditional Tuscan cuisine restaurant
- Elegant rooms in separate buildings
Country house
- Organic farm
- Wine cellar
- Cooking classes
From
US$ 545
/night
- Historic abbey with thousand-year-old charm
- Authentic Tuscan cooking classes available
- Stunning Italian gardens for relaxation
Farm stay
- Private pool
- Italian breakfast
- Outdoor garden
From
US$ 112
/night
- Private pool with beautiful garden views
- Italian breakfast with local ingredients
- Seasonal outdoor swimming pool
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
Farm stay
From
US$ 23
/night
Within a 10-minute drive of Church of Santa Maria, the Agriturismo Il Colombaio B&B includes 10 rooms.
Farm stay
- Outdoor pool
- Cozy restaurant
- On-site spa
From
US$ 237
/night
- Innovatively traditional local cuisine
- Scenic views of Tuscany's rolling hills
- Organic wines crafted on-site
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
- Wine baths
- Outdoor pool
- Tennis court
From
US$ 235
/night
- Vineyard-surrounded accommodations
- Wine therapy and massages available
- Panoramic pool with vineyard views
Farm stay
From
US$ 237
/night
Located 4.5 km from Piazza della Cisterna, this villa offers 7 rooms.
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
- Outdoor pool
- Table tennis
- Private parking
From
US$ 249
/night
- Seasonal outdoor pool with stunning views
- Farm stay with outdoor dining areas
- Table tennis for family fun
Farm stay
From
US$ 160
/night
Set 6 km from Castello di Monterinaldi, the rooms in the Podere Terreno Alla Via Della Volpaia Villa Radda in Chianti have views of garden.
Holiday home
- Outdoor Pool
- BBQ Facilities
- Spacious Patios
From
US$ 960
/night
- Eighteenth-century Tuscan farmhouse
- Modern apartments with outdoor patios
- Access to wellness at COMO Castello
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