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Search results; Over 1,000 homes in Highland Park

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Top guest favourite
Apartment in Highland Park
Green oasis in law suite
1 bedroom, 1 bed, 1 private bathroom
8–13 Sept
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5.0 out of 5 average rating, 66 reviews
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Home in Highland Park
North Shore - Home Away From Home
4 bedrooms, 5 beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 44 reviews
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Home in Highland Park
Cozy 2-Bedroom Cottage Near Downtown Highland Park
2 bedrooms, 2 queen beds, 1 bathroom
7–12 Sept
4.94 out of 5 average rating, 186 reviews
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Home in Highland Park
5 min to Ravinia*Navy Base*Sleeps 7*Smart TVs
3 bedrooms, 4 beds, 4 bathrooms
7–12 Sept
4.95 out of 5 average rating, 21 reviews
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Cottage in Highland Park
Re-imagined 1880s cottage by Highwood, Metra, Lake
2 bedrooms, 4 beds, 1 bathroom
19–24 Sept
4.98 out of 5 average rating, 114 reviews
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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, 166 reviews
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Home in Highland Park
6 bed pool Indoor Basketball Gym
6 bedrooms, 6 beds, 6.5 bathrooms
20–25 Nov
5.0 out of 5 average rating, 11 reviews
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Home in Highland Park
North Shore Blue-Door Bungalow
3 bedrooms, 4 beds, 1 bathroom
15–20 Sept
4.94 out of 5 average rating, 47 reviews
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Cottage in Highwood
The Pleasant Hill Cottage North Shore Enchantment
3 bedrooms, 6 beds, 2.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 17 reviews
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Flat in Highwood
Cozy Highwood Apt 4 BR 2 train stops to Naval Base
4 bedrooms, 5 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 8 reviews
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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, 153 reviews
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Home in Glenview
Charming Entire House
4 bedrooms, 4 beds, 2 bathrooms
8–13 Nov
4.98 out of 5 average rating, 85 reviews
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Home in Northbrook
6 Kings | Ping-Pong | Gazebo!
5 bedrooms, 6 king beds, 3.5 bathrooms
27 Sept – 2 Oct
4.9 out of 5 average rating, 52 reviews
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Guest suite in Riverwoods
Master qtr close to nature & easy urban facilities
1 bedroom, 2 beds, 1 bathroom
24–29 Oct
4.95 out of 5 average rating, 506 reviews
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Home in Des Plains
5 Star Luxury Stay Near Chicago O'hare Airport,
3 bedrooms, 5 beds, 2 bathrooms
6–11 Sept
4.98 out of 5 average rating, 95 reviews
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Home in Northbrook
1 Mi to Metra: Estate w/ Theater, Game Room & More
4 bedrooms, 4 beds, 7 bathrooms
7–12 Sept
5.0 out of 5 average rating, 5 reviews
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Home in Libertyville
Modern French Escape | Near Base
4 bedrooms, 5 beds, 2.5 bathrooms
15–20 Sept
4.97 out of 5 average rating, 60 reviews
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Home in Northbrook
*King bed *Outdoor Living *Sought-After Area
3 bedrooms, 3 beds, 1.5 bathrooms
13–18 Oct
4.98 out of 5 average rating, 132 reviews
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Flat in Evanston
Stylish & Comfy Gem near Downtown~Balcony~Parking
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
4.96 out of 5 average rating, 318 reviews