Holiday rentals in Chicago
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Top-rated holiday rentals in Chicago
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Chicago holiday rentals
Other great holiday rentals in Chicago
Superhost
Home in Robinson
4.71 out of 5 average rating, 21 reviewsJasper Junction Lodge
Holiday home in Medina
4.67 out of 5 average rating, 3 reviewsHunting and Fishing rental house. Medina ND.
Guest favourite
Home in Dawson
4.92 out of 5 average rating, 26 reviewsSerenity Lodging. Hunt, Fish, Play, Relax, Enjoy!
Guest favourite
Home in Gackle
5.0 out of 5 average rating, 7 reviewsOutdoor Getaway
Ranch in Pingree
4.9 out of 5 average rating, 21 reviewsBison Ranch Lodge
Guest favourite
Bungalow in Robinson
4.96 out of 5 average rating, 26 reviewsGreenhead Lodge of Robinson North Dakota
Home in Medina
4.63 out of 5 average rating, 8 reviewsMedina Hunting House
Guest favourite
Home in Jamestown
4.9 out of 5 average rating, 51 reviewsSpacious 3 bedroom Craftsman style home Jamestown
Destinations to explore
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
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- Holiday Apartments Australia
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- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
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- Apartments with a Hot Tub United States
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- Pet-Friendly Vacation Rentals United States
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- Luxury Dog-Friendly Cottages United Kingdom