Top Holiday rentals in Chianti
Find the Top Holiday rentals in Chianti – 80+ Quality Options from Leading Providers
41-60 out of 81 holiday rentals
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Farm stay
4 adults
2 bedrooms
4 beds
From
US$ 199
/night
- Private pool with garden views
- On-site cooking classes available
- Air-conditioned units with kitchenettes
Country house
3 adults
1 bedroom
2 beds
From
US$ 142
/night
- Outdoor swimming pool with views
- Rustic-style rooms with garden access
- On-site spa services available
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
- Outdoor pool
- Historic apartments
- On-site restaurant
From
US$ 505
/night
- Authentic Florentine castle experience
- Stunning Tuscan garden views
- Ideal romantic wedding venue
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
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
Apartment
- Infinity Pool
- Family Restaurant
- On-site Spa
From
US$ 282
/night
- Infinity pool with stunning views
- Family-friendly restaurant with local dishes
- On-site massages and wellness spa
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
- Private entrance
- Outdoor terrace
- Fully equipped kitchen
From
US$ 185
/night
- Private entrance for added privacy
- Outdoor dining terrace with garden views
- Activities like cycling and hiking available
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
Apartment
- Garden
- Barbecue
- Kitchen
From
US$ 187
/night
- Historic building with beautiful gardens
- Private check-in and check-out options
- Barbecue facilities for outdoor dining
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