Highland Vacation Rentals, Houses & More


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Areas near Highland

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1 / 17

1821

  • 4
  • 9
  • Min stay varies

$118

Details

Great rentals within 30 miles that match your search

1 / 11

Luxury 2500 sq. ft. of executive lower level space

  • 2
  • 4
  • 1 night min

$200

Details

1 / 7

CONDO FOR RENT IN FLORIDA

  • 1
  • 4
  • 90 nights min

$57

Details

1 / 33

Lux Beachfront Slps 29, Chicago-40min, 2+ Ngt quotes NOT accurate, Please ask!

  • 6
  • 29
  • 2 nights min

$409

Details

1 / 25

Beachfront Guesthouse Slps8, Chicago-40min, 2+Ngt Quotes NOT Accurate, pls. ask!

  • 2
  • 8
  • 2 nights min

$129

Details

1 / 29

Lux Beachfront Slps 19, Chicago-40min, 2+ Ngt quotes NOT accurate, please ask!

  • 4
  • 19
  • 2 nights min

$279

Details

1 / 10

Miller Beach Tree House in Indiana Dunes

  • 3
  • 6
  • Min stay varies

$111

Details

1 / 26

Park Forest 597 - Shuttle to Lifts/Town

  • 3
  • 10
  • Min stay varies

$305

Details

1 / 31

Beachfront Villa Slps 30, Chicago-40min, 2+ Ngt quotes NOT Accurate, please ask!

  • 6
  • 30
  • 2 nights min

$560

Details

1 / 18

*******th Street, East

  • Studio
  • 8
  • Min stay varies

$372

Details

1 / 21

*******th Street, West

  • Studio
  • 8
  • Min stay varies

$372

Details

1 / 15

Beautiful Home near Chicago, IL

  • 4
  • 8
  • 2 nights min

$425

Details

1 / 11

Cozy quarters steps away from Chicago's lakefront

  • 1
  • 3
  • 1 night min

$80

Details

1
1 / 16

5 Bdrm 3 Bth Lake Michigan Waterfront Private Pool

  • 5
  • 20
  • 3 nights min

$995

Details

1
1 / 8

Guest House in Private Gated Nudist Community

  • 1
  • 2
  • 2 nights min

$140

Details

1 / 26

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

  • 3
  • 6
  • Min stay varies

$750

Details

1 / 5

Eclectic Artists Flat

  • 1
  • 4
  • 1 night min

$115

Details

2
1 / 25

Historic Chicago Style Bungalow Business Ready

  • 3
  • 6
  • 2 nights min

$190

Details

1 / 11

Make It Your Own - 15 Minutes to Chicago

  • 1
  • 4
  • 1 night min

$109

Details

1 / 4

Condo

  • 2
  • 4
  • 1 night min

$445

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 / 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 / 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 - Purple Bedroom

  • 4
  • 1
  • 7 nights min

$43

Details

16
1 / 16

Lighthouse apt. Great location right by Lighthouse Outlet Mall See the Sale!

  • 1
  • 3
  • 2 nights min

$100

Details

19
1 / 16

Beautiful apt next to Lighthouse Outlet Mall

  • 1
  • 3
  • 2 nights min

$100

Details

14
1 / 16

Lighthouse Apartment Rental

  • 2
  • 4
  • 2 nights min

$130

Details

11
1 / 13

Beautiful apt. across from Lighthouse Mall

  • 1
  • 2
  • 2 nights min

$100

Details

1 / 18

Il Giardino

  • 3
  • 8
  • 3 nights min

$229

Details

6
1 / 14

Ideal Family Getaway Home! 2bed 2bath sleeps 6, golf cart included!

  • 2
  • 6
  • Min stay varies

$229

Details

3
1 / 27

Family Friendly Cottage just steps to Sandcastle Park - Includes Golf Cart

  • 2
  • 8
  • Min stay varies

$300

Details

1 / 9

6 Bedroom Home in Western Suburbs with Heated Pool

  • 6
  • 15
  • 3 nights min

$650

Details

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