Top Holiday homes in Chianti
Find the Top Holiday homes in Chianti – 100+ Quality Options from Leading Providers
21-40 out of 136 holiday homes
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Farm stay
4 adults
1 bedroom
2 beds
From
US$ 331
/night
- Vineyard-surrounded accommodations
- Wine therapy and massages available
- Panoramic pool with vineyard views
Farm stay
6 adults
2 bedrooms
3 beds
From
US$ 121
/night
- Seasonal outdoor swimming pool
- Family-friendly children's playground
- Picnic area with barbecue
Farm stay
- Swimming pool
- Cooking class
- Fitness centre
From
US$ 554
/night
- 19th-century country house ambiance
- Olive grove surroundings with scenic views
- On-site cooking classes available
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
Farm stay
- Outdoor Pool
- Traditional Restaurant
- Bicycle Rental
From
US$ 165
/night
- Tuscan cuisine with local wines
- Outdoor pool with vineyard views
- Bicycle rental for exploring surroundings
Farm stay
- Wine Tasting
- Swimming Pool
- Tennis Court
From
US$ 344
/night
- Historic former convent accommodations
- Extensive wine tour and tasting experiences
- Outdoor swimming pools with stunning views
Farm stay
- Outdoor fireplace
- Bicycle rental
- Children's playground
From
US$ 1 167
/night
- Outdoor swimming pool with views
- Yoga and fitness classes available
- Activities like cycling and cooking classes
Country house
- Cooking school
- Infinity pool
- Wellness spa
From
US$ 369
/night
- Tuscan cooking classes with local ingredients
- Infinity pool overlooking Antinori vineyards
- Wellness spa with sauna and hammam
Farm stay
From
US$ 204
/night
This farm stay is a 10-minute drive from Azienda Agricola Vallepicciola and offers hiking, horseback riding and cycling.
Country house
- Mediterranean Garden
- Swimming Pool
- Boutique Accommodations
From
US$ 242
/night
- 14th-century restored watermill hotel
- Extensive Mediterranean garden with pool
- Daily buffet breakfast with local products
Country house
- Saltwater pool
- In-house restaurant
- Tennis court
From
US$ 266
/night
- Saltwater seasonal outdoor pool
- In-house traditional restaurant
- Billiards and tennis facilities
Farm stay
- Outdoor pool
- On-site restaurant
- Pet-friendly
From
US$ 300
/night
- Farm-to-table Tuscan dining experiences
- Wine and olive oil production on-site
- Rustic-chic wedding venue options
Farm stay
- Outdoor pool
- Wine cellar
- Fine dining
From
US$ 288
/night
- Wine tastings in historic Chianti cellar
- Elegant restaurant with Tuscan cuisine
- Historic medieval architecture on-site
Farm stay
- Infinity pool
- On-site restaurant
- Wellness spa
From
US$ 274
/night
- Traditional Tuscan cuisine with own wines
- Infinity pool with panoramic views
- Spa with Turkish bath and massages
Country house
- Private parking
- Fitness classes
- Picnic area
From
US$ 242
/night
- On-site spa with wellness treatments
- Outdoor swimming pool with garden views
- Bicycle rental for nearby exploration
Holiday home
- Sun terrace
- Private parking
- Children's play area
From
US$ 140
/night
- Private entrance with full-day security
- Garden views from outdoor dining area
- Bike rentals and local culture tours
Farm stay
- Outdoor pool
- On-site restaurant
- Wine cellar
From
US$ 247
/night
- Charming villa with historic features
- On-site wine production and tasting tours
- Contemporary cuisine at Osteria 1126
Farm stay
- Outdoor pool
- Wine bar
- Cooking classes
From
US$ 259
/night
- 15th-century restored apartments
- On-site wine tasting sessions
- Saltwater seasonal pool
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
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
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