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6 Holiday homes in Chicago

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To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more
6 Results  |  
23 Photos

Apartment | 3 Bedrooms | sleeps 8

Excellent 5/5 

3 Nights min stay

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from £199 /night

£1389 - £1989 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Huge sunny loft, dream kitchen, two full bathrooms & brand new Sealy beds - all just steps to everything and everywhere: in Lincolnn Park near Whole Foods, steps to the red line to downtown, North Ave bus to Wicker Park/Bucktown, Halsted bus to Greektown or Boystown  …see more

4 Photos

Riad | 1 Bedroom | sleeps 1

1 night min stay

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from £18 /night

£124 - £620 / week

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Key info:

  • Not suitable for children
  • No pets allowed
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7 Photos

Condo | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £150 /night

£1046 - £1593 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car not necessary
  • Air conditioning
  • No pets allowed
Beautiful Gulf & Bay Club BAYSIDE condominium is located on the island of Siesta Key, offering luxury accommodations in a tropical paradise  …see more

9 Photos

House | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £574 /night

£4012 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • Pets welcome
The perfect getaway – An ocean-front vacation home just north of Santa Cruz in the quaint town of Davenport  …see more

24 Photos

Condo | 1 Bedroom | sleeps 4

1 night min stay

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from £81 /night

£567 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • Air conditioning
  • No pets allowed
Lake view 1 bedroom condo:- 1 full bed, sleeps 2  …see more

4 Photos

Barn | 5 Bedrooms | sleeps 8

Min stay varies

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Key info:

  • Beach / lakeside relaxation
  • Not suitable for children
  • Car advised
  • No pets allowed
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