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Search results; Over 1,000 homes in Highland Park

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Top guest favourite
Cottage in Highland Park
Re-imagined 1880s cottage by Highwood, Metra, Lake
2 bedrooms, 4 beds, 1 private bathroom
11–16 Oct
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4.98 out of 5 average rating, 115 reviews
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Top guest favourite
Home in Highland Park
North Shore - Home Away From Home
4 bedrooms, 5 beds, 2 bathrooms
13–18 Oct
4.98 out of 5 average rating, 45 reviews
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Top guest favourite
Home in Highland Park
5 min to Ravinia*Navy Base*Sleeps 7*Smart TVs
3 bedrooms, 4 beds, 4 bathrooms
8–13 Oct
4.96 out of 5 average rating, 23 reviews
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Guest favourite
Home in Highland Park
Cozy 2-Bedroom Cottage Near Downtown Highland Park
2 bedrooms, 2 queen beds, 1 bathroom
20–25 Sept
4.93 out of 5 average rating, 192 reviews
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Guest favourite
Flat in Highland Park
Lovely studio near the beach! (and heated floors!)
1 bedroom, 1 queen bed, 1 bathroom
25–30 Oct
4.92 out of 5 average rating, 209 reviews
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Top guest favourite
Home in Highland Park
6 bed pool Indoor Basketball Gym
6 bedrooms, 6 beds, 6.5 bathrooms
28 Dec – 4 Jan
5.0 out of 5 average rating, 11 reviews
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Top guest favourite
Home in Highland Park
North Shore Blue-Door Bungalow
3 bedrooms, 4 beds, 1 bathroom
3–8 Oct
4.94 out of 5 average rating, 47 reviews
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Guest favourite
Flat in Highwood
Cozy Highwood Apt 4 BR 2 train stops to Naval Base
4 bedrooms, 5 beds, 1 bathroom
21–26 Sept
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Cottage in Highwood
The Pleasant Hill Cottage North Shore Enchantment
3 bedrooms, 6 beds, 2.5 bathrooms
11–16 Oct
5.0 out of 5 average rating, 18 reviews
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Top guest favourite
Guest suite in Highland Park
Charming space w/ use of deck and yard
1 bedroom, 2 queen beds, 1 bathroom
28 Sept – 3 Oct
4.97 out of 5 average rating, 167 reviews
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Top guest favourite
Home in Northbrook
*King bed *Outdoor Living *Sought-After Area
3 bedrooms, 3 beds, 1.5 bathrooms
10–15 Nov
4.98 out of 5 average rating, 134 reviews
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Guest favourite
Home in Des Plains
Sleeps 24+ Luxury house Near Chicago 12 king beds
11 bedrooms, 12 king beds, 6.5 bathrooms
5–10 Oct
5.0 out of 5 average rating, 20 reviews
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Top guest favourite
Home in Des Plains
Luxury 4 Bed 2.5 Bath near Chicago O'Hare Airport
4 bedrooms, 4 beds, 2.5 bathrooms
25–30 Oct
4.88 out of 5 average rating, 158 reviews
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Top guest favourite
Guest suite in Northbrook
Elegant 2BR/2BA Northshore Garden Apartment
2 bedrooms, 3 beds, 2 bathrooms
19–24 Oct
4.92 out of 5 average rating, 106 reviews
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Top guest favourite
Home in Lake Forest
Spacious Home-Great Lakes Close-Quiet Location
5 bedrooms, 5 beds, 4 bathrooms
24–29 Sept
5.0 out of 5 average rating, 37 reviews
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Top guest favourite
Home in North Chicago
J&J Vacay “Your Navy Graduation Destination”
4 bedrooms, 6 beds, 2.5 bathrooms
16–21 Oct
4.97 out of 5 average rating, 65 reviews
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Guest favourite
Home in Northbrook
1 Mi to Metra: Estate w/ Theater, Game Room & More
4 bedrooms, 4 beds, 7 bathrooms
21–26 Sept
5.0 out of 5 average rating, 5 reviews
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Home in Highland Park
Fresh and stylish family home near Lake Michigan
3 bedrooms, 5 beds, 2.5 bathrooms
22–27 Sept
4.86 out of 5 average rating, 7 reviews
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Top guest favourite
Home in Arlington Heights
Peaceful Home in AH
3 bedrooms, 3 beds, 2 bathrooms
18–23 Oct
4.97 out of 5 average rating, 38 reviews