Highland Park Rentals

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18 Houses

20

Highland Park Luxury Home- 2000 square foot Suite

Lake County / Highland Park

Highland Park b and b

2 8 2 nights min

  • 2 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Car not necessary
  • Air conditioning

Price per night from

$115

Price per night from

$115

Great rentals within 20 miles that match your search

Distance approx 9.6 km from Highland Park

16

Rare! Spacious Private 5 Beds for the Holidays

Lake County / Buffalo Grove

Buffalo Grove house

5 10 1 night min

  • 5 bedrooms
  • sleeps 10
  • 1 night min
  • Child Friendly

Price per night from

$315

Responds fast!
avg. 1 hour 19 minutes

Price per night from

$315

Distance approx 7.7 km from Highland Park Show on Map

(2) Excellent 

30

Beautifully Remodeled 3 BR Townhouse near Chicago

Illinois / Wilmette

Wilmette townhouse

3 10 2 nights min

  • 3 bedrooms
  • sleeps 10
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$149

Responds fast!
avg. 1 hour 10 minutes

Price per night from

$149

Distance approx 15.06 km from Highland Park

8

Take A Pebble Apartments (Studio)

Lake County / Lake Zurich

Lake Zurich apartment

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Air conditioning

Price per night from

$114

Price per night from

$114

Distance approx 7.87 km from Highland Park Show on Map

(3) Very Good 

27

Completely Remodeled 3-Bedroom House!

Illinois / Wheeling

Wheeling house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$138

Responds fast!
avg. 1 hour 10 minutes

Price per night from

$138

Distance approx 12.33 km from Highland Park

15

Sleep Aboard Adeline’s Sea Moose: 68 ft Private Yacht Rentals Chicago Downtown

Illinois / Lincolnwood

Lincolnwood yacht

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$1,379

Price per night from

$1,379

Distance approx 17.67 km from Highland Park

23

Vintage 3BR in Lake View by Sonder

Illinois / Lincolnwood

Lincolnwood apartment

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$57

Responds fast!
avg. 1 hour 52 minutes

Price per night from

$57

Distance approx 14.68 km from Highland Park

24

Luxe Chicago Townhome w/ Balcony - 20 Mins to DT!

Illinois / Lincolnwood

Lincolnwood house

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Air conditioning

Price per night from

$144

Responds fast!
avg. 7 minutes

Price per night from

$144

Distance approx 10.56 km from Highland Park

7

Pinewoods Retreat - Private Room

Illinois / Evanston

Evanston room

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$59

Price per night from

$59

Distance approx 17.67 km from Highland Park

(1) Excellent 

18

Handsome 3BR in Lake View by Sonder

Illinois / Lincolnwood

Lincolnwood apartment

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$62

Responds fast!
avg. 2 hours 6 minutes

Price per night from

$62

Distance approx 12.5 km from Highland Park

22

Hull Chateau

Illinois / Evanston

Evanston house

2 7 1 night min

  • 2 bedrooms
  • sleeps 7
  • 1 night min
  • Nearest beach 2 mi
  • Child Friendly
  • Car not necessary

Price per night from

$255

Price per night from

$255

Distance approx 17.52 km from Highland Park

9

Barrington Village Townhome B

Illinois / Barrington

Barrington townhouse

2 5 28 nights min

  • 2 bedrooms
  • sleeps 5
  • 28 nights min
  • Child Friendly

Price per night from

$181

Price per night from

$181

Distance approx 15.88 km from Highland Park

24

Opulent Historic 2BR Apartment in Andersonville w/ Contemporary Kitchen

Illinois / Lincolnwood

Lincolnwood apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$173

Price per night from

$173

Distance approx 15.48 km from Highland Park

29

Elegantly Updated Albany Park 4BR/3.5BA w/ Private Fenced Yard & Garage

Illinois / Lincolnwood

Lincolnwood house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$263

Price per night from

$263

Distance approx 17.87 km from Highland Park

21

Grand 3BR in Roscoe Village by Sonder

Illinois / Lincolnwood

Lincolnwood condo

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$132

Responds fast!
avg. 2 hours 6 minutes

Price per night from

$132

Distance approx 2.04 km from Highland Park Show on Map

33

Exquisite Interior Designer’s House Short Walk to Lake Michigan

Lake County / Highwood

Highwood house

4 6 min stay varies

  • 4 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 0.5 mi
  • Child Friendly
  • Air conditioning

Price per night from

$460

Price per night from

$460

Distance approx 17.79 km from Highland Park

12

Comfy Quarters

Illinois / River Grove

River Grove house

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Car not necessary
  • Air conditioning
  • Private garden

Price per night from

$104

Price per night from

$104

Distance approx 19.23 km from Highland Park

9

OAK PARK BEAUTIFUL, HISTORICAL, CONVENIENT TO PUBLIC TRANSPORTATION, AIRPORTS

Illinois / Oak Park

Oak Park b and b

1 3 2 nights min

  • 1 bedroom
  • sleeps 3
  • 2 nights min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$40

Responds fast!
avg. 3 hours 44 minutes

Price per night from

$40