Top Vacation homes in Chianti

Find the Top Vacation homes in Chianti – 100+ Quality Options from Leading Providers

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22 Guests, 1 Room
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81-100 out of 185 vacation homes
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Farm stay
5 adults
3 bedrooms
3 beds
From   US$ 249 /nightSelect
  • Seasonal outdoor pool with stunning views
  • Free private parking available for guests
  • Outdoor garden dining area for relaxation
5 adults
1 bedroom
3 beds
From   US$ 219 /nightSelect
  • Infinity pool with panoramic views
  • On-site cooking classes available
  • Outdoor play area for children
Farm stay
  • Outdoor Pools
  • Fitness Centre
  • Picnic Area
From   US$ 359 /nightSelect
  • Family-friendly restaurant with Italian cuisine
  • Two seasonal outdoor pools with views
  • Activities like cycling and walking tours
  • Outdoor Pool
  • Free Parking
  • Pet Friendly
From   US$ 284 /nightSelect
  • Surrounded by vineyards and olive groves
  • Rustic-style apartments with kitchenette
  • Seasonal outdoor swimming pool
  • Infinity Pool
  • Cookery Classes
  • Bicycle Rentals
From   US$ 314 /nightSelect
  • Cooking lessons with traditional recipes
  • Infinity pool with panoramic views
  • Free mountain bike rentals available
Holiday home
  • Yoga Classes
  • Outdoor Pool
  • Picnic Area
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  • Yoga classes offered on-site
  • Seasonal outdoor pool with view
  • Outdoor dining area and picnic space
  • Seasonal pool
  • Family rooms
  • Private check-in
From   US$ 139 /nightSelect
  • Seasonal outdoor pool with views
  • In-house restaurant with gluten-free options
  • Pet-friendly accommodations available
From   US$ 139 /nightSelect
While staying at the smoke-free Castello Di Selvole Vagliagli you are invited to discover Meleto Castle, set 4.1 miles away, or La Fornace Art Gallery, which is about a 15-minute stroll away.
Farm stay
  • On-site Spa
  • Countryside Views
  • Flat-screen TVs
From   US$ 131 /nightSelect
  • Relaxing on-site spa services
  • Spectacular views of the countryside
  • Flat-screen TVs in all rooms
  • Saltwater Pool
  • Spa Services
  • Horse Stables
From   US$ 176 /nightSelect
  • Rustic apartments with Tuscan countryside views
  • Saltwater pool with scenic surroundings
  • Home-baked breakfast options available
  • Outdoor Dining
  • Garden
  • Seasonal Pool
From   US$ 130 /nightSelect
  • Tuscan-style rustic rooms
  • On-site Vernaccia and Chianti production
  • Seasonal outdoor pool with views
Farm stay
  • Infinity Pool
  • Wine Bar
  • On-site Spa
From   US$ 515 /nightSelect
  • Infinity pool with stunning vineyard views
  • On-site wine tastings with expert guidance
  • Adults-only atmosphere for tranquil retreats
Farm stay
  • Ayurvedic spa
  • Outdoor pool
  • Vineyard tours
From   US$ 344 /nightSelect
  • Owns vineyard producing Chianti Classico wine
  • Offers Ayurvedic massages and spa services
  • Historic 11th-century renovated villa accommodations
Country house
  • Infinity Pool
  • On-site Restaurant
  • Private Terraces
From   US$ 427 /nightSelect
  • Authentic Tuscan cuisine and tasting menu
  • 7x14 meter swimming pool with Jacuzzi
  • Stunning views of San Gimignano
  • Infinity Pool
  • Bike Rental
  • Outdoor Playground
From   US$ 154 /nightSelect
  • Infinity pool with scenic views
  • Cycling and hiking opportunities available
  • Buffet breakfast with local specialties
  • Outdoor pool
  • Children's playground
  • Free parking
From   US$ 274 /nightSelect
  • Working farm with olive oil and wine
  • Rustic apartments in antique buildings
  • Infinity pool with scenic views
Country house
  • Outdoor pool
  • Cookery courses
  • On-site restaurant
From   US$ 149 /nightSelect
  • Panoramic valley views from pool
  • Authentic Tuscan dishes on terrace
  • Individual room designs with art
Country house
  • Swimming Pool
  • Bicycle Rental
  • Garden
From   US$ 162 /nightSelect
  • Refurbished colonial house with Tuscan charm
  • Outdoor swimming pool with scenic views
  • Bicycle rental for exploring Tuscany
Farm stay
  • Free parking
  • Air conditioning
  • Shared lounge
From   US$ 124 /nightSelect
  • Adults-only atmosphere for relaxation
  • Terracotta floors and wood-beamed ceilings
  • Complimentary welcome drink upon arrival
  • Scenic Pool
  • Picnic Area
  • Outdoor Dining
From   US$ 108 /nightSelect
  • Pool with scenic views
  • Italian breakfast with local specialties
  • Spacious picnic area