Top Vacation homes in Chianti
Find the Top Vacation homes in Chianti – 100+ Quality Options from Leading Providers
1-20 out of 185 vacation homes
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Farm stay
4 adults
1 bedroom
3 beds
From
US$ 124
/night
- Bicycle rental and tour desk available
- Picnic area with barbecue facilities
- Pets allowed on the property
9 adults
4 bedrooms
5 beds
From
US$ 505
/night
- Authentic medieval castle experience
- Gorgeous Tuscan hill views
- On-site Italian restaurant serving local cuisine
Farm stay
- Infinity pool
- Wine tours
- Cooking classes
From
US$ 248
/night
- Historic castle with on-site Chianti vineyard
- Elegant rooms with classic Tuscan style
- Renaissance-style restaurant for traditional cuisine
Country house
- Wine cellar
- Tuscan restaurant
- Bicycle rental
From
US$ 348
/night
- Guided wine cellar tours available
- Authentic Tuscan cuisine restaurant
- Historic medieval country village setting
Country house
- Panoramic Pools
- On-site Restaurant
- Lounge Bar
From
US$ 973
/night
- Breathtaking Chianti Classico views
- Refined Tuscan dining experience
- Exclusive D'Wine Club access
- Private villas
- Outdoor swimming pool
- Wine estate
From
US$ 252
/night
- 11th century Medici villa experience
- Exclusive wine and olive oil tasting
- Stunning gardens and terraces
Farm stay
- Outdoor pool
- On-site restaurant
- Bicycle rental
From
US$ 394
/night
- 11th-century castle with stunning views
- Traditional Tuscan dining experiences
- Outdoor swimming pool with panoramic views
Farm stay
- Infinity Pool
- Wine Bar
- On-site Spa
From
US$ 515
/night
- Infinity pool with stunning vineyard views
- On-site wine tastings with expert guidance
- Adults-only atmosphere for tranquil retreats
Farm stay
- Outdoor pool
- Kids' club
- Spa treatments
From
US$ 168
/night
- Wellness spa with diverse treatments
- Seasonal outdoor pool with view
- Family-friendly activities available
Farm stay
- Outdoor Pool
- Wine Tastings
- Cooking Classes
From
US$ 422
/night
- Historic winery with stunning vineyard views
- Authentic Tuscan dining experience at Il Cavaliere
- Outdoor activities like wine tasting and trekking
Farm stay
- Outdoor Pool
- On-site Restaurant
- E-bike Rental
From
US$ 517
/night
- Traditional Tuscan cuisine with organic ingredients
- Exclusive outdoor pool in the countryside
- E-bike rental to explore the Chianti hills
Country house
- Wellness Spa
- Scenic Pool
- Bicycle Rentals
From
US$ 180
/night
- On-site wellness spa with massage services
- Scenic pool with garden views
- Bicycle rentals for local exploration
Farm stay
- Infinity Pool
- Sauna
- Restaurant
From
US$ 274
/night
- Traditional Tuscan cuisine with house wines
- Infinity pool with panoramic views
- On-site olive oil and wine tastings
Farm stay
- Salt-water pool
- Organic vineyard
- Tuscan restaurant
From
US$ 380
/night
- Eco-friendly organic vineyards with tastings
- Gourmet Tuscan dining on the veranda
- Outdoor salt-water pool with scenic views
Farm stay
- Infinity Pool
- Bike Rentals
- On-site Spa
From
US$ 114
/night
- Organic wine and olive oil production
- Rustic-style apartments with kitchenettes
- Outdoor infinity pool with views
Farm stay
- Outdoor Pool
- Restaurant
- Bicycle Rental
From
US$ 165
/night
- Tuscan cuisine with fine local wines
- Scenic outdoor pool with views
- Bicycle rental for local exploration
Farm stay
- Outdoor pool
- BBQ facilities
- Bicycle rental
From
US$ 449
/night
- Self-catering apartments with terraces
- Scenic outdoor pool with views
- Activities like hiking and cycling
Farm stay
- Infinity Pool
- Organic Farm
- Cooking Classes
From
US$ 185
/night
- Organic wine and olive oil production
- Infinity pool with vineyard views
- Traditional Tuscan cooking classes
Country house
- Outdoor Pool
- Large Garden
- Bar Area
From
US$ 143
/night
- 1400s estate with stunning countryside views
- Outdoor pool surrounded by olive groves
- Breakfast served on the lovely terrace
Farm stay
- Outdoor Pool
- Restaurant
- Garden
From
US$ 243
/night
- Panoramic views of medieval towers
- Traditional Tuscan cuisine restaurant
- Outdoor swimming pool with a view
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