Top Vacation homes in Chicago Metropolitan Area

Find the Top Vacation homes in Chicago Metropolitan Area – 10+ Quality Options from Leading Providers

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22 Guests, 1 Room
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1-13 out of 13 vacation homes
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Holiday home
From   US$ 793 /nightSelect
  • Five-bedroom holiday home with patio
  • Grocery delivery and barbecue facilities
  • Access to skiing and hiking activities
Holiday home
26 adults
7 bedrooms
9 beds
From   US$ 1 552 /nightSelect
  • Beachfront property with lake views
  • Hot tub/Jacuzzi for relaxation
  • Family rooms with various amenities
  • Private Beach
  • Fitness Centre
  • Children's Playground
From   US$ 508 /nightSelect
  • Private beach access for exclusive relaxation
  • On-site fitness classes and activities available
  • Family-friendly restaurant with outdoor dining
  • Driveway Parking
  • Outdoor Dining
  • Pet-Friendly
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  • 5 bedrooms accommodate large groups
  • Driveway parking available for guests
  • Outdoor dining area for gatherings
  • Private Entrance
  • Electric Charging
  • Flat-Screen TV
From   US$ 1 891 /nightSelect
  • Five spacious bedrooms for families
  • Private entrance for added privacy
  • Electric vehicle charging station available
  • Business Centre
  • Free Parking
  • Breakfast Options
From   US$ 49 /nightSelect
  • 24-hour business centre with services
  • Buffet or continental breakfast offered
  • Free private parking available onsite
  • Outdoor dining
  • Private check-in
  • Picnic area
From   US$ 480 /nightSelect
  • Private entrance for added privacy
  • Fully equipped kitchen for cooking meals
  • Outdoor dining area with garden views
  • Lake Views
  • Fireplace
  • Swimming Pool
From   US$ 182 /nightSelect
  • Stunning lake and sea views
  • Cozy fireplace for comfort
  • Inviting on-site swimming pool
  • Private Entrance
  • Flat-Screen TV
  • Fully Equipped Kitchen
From   US$ 112 /nightSelect
  • Private entrance for added privacy
  • Flat-screen TV with cable channels
  • Fully equipped kitchen for cooking
  • Private parking
  • Flat-screen TV
  • Security features
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  • Private entrance with full-day security
  • Indoor play area for children
  • Streaming services on flat-screen TV
  • Private Parking
  • Fully Equipped Kitchen
  • Garden Terrace
From   US$ 442 /nightSelect
  • Garden views from spacious balcony
  • Free private parking for guests
  • Pet-friendly accommodations available
  • Air conditioning
  • Washing machine
  • TV
From   US$ 159 /nightSelect
  • Private entrance for enhanced privacy
  • Fully equipped kitchen with cookware
  • Non-smoking property for clean atmosphere
  • Beach Access
  • Game Room
  • Private Entrance
From   US$ 271 /nightSelect
  • Beach access just steps away
  • Fully equipped kitchen available
  • Game room with table tennis