Westchester Vacation Rentals, Houses & More


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Areas near Westchester

Great rentals within 30 miles that match your search

1 / 11

Make It Your Own - 15 Minutes to Chicago

  • 1
  • 4
  • 1 night min

$109

Details

2
1 / 25

Historic Chicago Style Bungalow Business Ready

  • 3
  • 6
  • 2 nights min

$191

Details

1 / 4

Condo

  • 2
  • 4
  • 1 night min

$446

Details

1 / 23

Beautiful 5 Bed in Heart of Oak Park Sleeps 2-11+

  • 5
  • 11
  • 1 night min

$225

Details

1 / 14

Oak Park Beauty Sleeps 1 to 8 Guests

  • 3
  • 9
  • 1 night min

$140

Details

1 / 4

Charming artist's home close to everything!

  • 2
  • 4
  • 2 nights min

$99

Details

1 / 5

Eclectic Artists Flat

  • 1
  • 4
  • 1 night min

$115

Details

1 / 10

Serene 4/Bedroom House in Lombard

  • 4
  • 10
  • 1 night min

$250

Details

1 / 18

Comfy Quarters

  • 1
  • 2
  • 1 night min

$57

Details

1 / 7

Humphrey Homestay - Purple Bedroom

  • 4
  • 1
  • 7 nights min

$43

Details

1 / 7

Humphrey Homestay - Yellow Room, Bed 1

  • 1
  • 1
  • 7 nights min

$25

Details

1 / 7

Humphrey Homestay - Yellow Bedroom, Bed 2

  • 1
  • 1
  • 7 nights min

$25

Details

1 / 7

Humphrey Homestay - Green Room

  • 1
  • 1
  • 7 nights min

$30

Details

1 / 6

Humphrey Homestay - Blue Bedroom

  • 1
  • 1
  • 7 nights min

$30

Details

1 / 26

NEW! 3BR Burr Ridge House on 5 Manicured Acres!

  • 3
  • 6
  • Min stay varies

$750

Details

1 / 9

6 Bedroom Home in Western Suburbs with Heated Pool

  • 6
  • 15
  • 3 nights min

$650

Details

8
1 / 37

The Davis House, Landmarked 1892 Farm House

  • 3
  • 8
  • Min stay varies

$20

Details

1 / 25

Large 2 BR 1 BR Apartment 20 mins from DT Chicago

  • 2
  • 4
  • 2 nights min

$133

Details

1 / 81

Fantastic Huge Home, Heated Pool 8 bedrooms & MORE

  • 8
  • 16
  • 1 night min

$999

Details

1 / 11

Cozy quarters steps away from Chicago's lakefront

  • 1
  • 3
  • 1 night min

$80

Details

1 / 7

Pinewoods Retreat - Private Room

  • 1
  • 3
  • 1 night min

$51

Details

1
1 / 30

Beautifully Remodeled 3 BR Townhouse near Chicago

  • 3
  • 10
  • Min stay varies

$140

Details

18
1 / 8

Just north of Chicago

  • 2
  • 4
  • 1 night min

$110

Details

1
1 / 22

Upscale Suburban Neighborhood

  • 1
  • 3
  • 7 nights min

$57

Details

1 / 21

Upscale Suburban Neighborhood

  • 1
  • 2
  • 2 nights min

$59

Details

1 / 20

Upscale Suburban Neighborhood

  • 1
  • 2
  • 2 nights min

$55

Details

1 / 26

Completely Remodeled 3-Bedroom House!

  • 3
  • 8
  • Min stay varies

$120

Details

1 / 13

Beautiful Home on Chicago's North Shore

  • 4
  • 8
  • 4 nights min

$275

Details

1 / 21

Gorgeous Three-Bedroom Townhouse

  • 3
  • 10
  • Min stay varies

$130

Details

1 / 5

Ellogent and Affordable

  • 1
  • 2
  • 2 nights min

$70

Details

1 / 15

Beautiful Home near Chicago, IL

  • 4
  • 8
  • 2 nights min

$425

Details

1 / 5

Cozy Urban Country Home

  • 1
  • 3
  • 2 nights min

$65

Details

1 / 20

Highland Park Luxury Home- 2000 square foot Suite

  • 2
  • 8
  • 2 nights min

$110

Details

1 / 12

Take A Pebble Apartments (Studio)

  • 1
  • 2
  • 1 night min

$59

Details

1
1 / 32

A Spacious & Fabulous Home

  • 5
  • 12
  • 1 night min

$350

Details

1 / 26

Park Forest 597 - Shuttle to Lifts/Town

  • 3
  • 10
  • Min stay varies

$305

Details

1 / 17

1821

  • 4
  • 9
  • Min stay varies

$118

Details

1 / 8

PEACEFUL COMFORT with Free Parking

  • 1
  • 3
  • 1 night min

$70

Details

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