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Search results; Over 1,000 homes in Highland Park

Guest favourite
Home in Highland Park
2-Acre Highland Park Retreat with Heated Pool ~ 5*
6 bedrooms, 6 beds, 4 private bathrooms
20–25 Sept
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4.91 out of 5 average rating, 151 reviews
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, 191 reviews
Top guest favourite
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, 115 reviews
Top guest favourite
Home in Highland Park
North Shore - Home Away From Home
4 bedrooms, 5 beds, 2 bathrooms
21–26 Sept
4.98 out of 5 average rating, 45 reviews
Top guest favourite
Home in Highland Park
North Shore Blue-Door Bungalow
3 bedrooms, 4 beds, 1 bathroom
23–28 Sept
4.94 out of 5 average rating, 47 reviews
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
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
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, 166 reviews
Guest favourite
Home in Northbrook
*King beds*Modern* Renovated*North Shore
4 bedrooms, 4 beds, 2.5 bathrooms
17–22 Sept
4.82 out of 5 average rating, 11 reviews
Top guest favourite
Home in Glenview
Charming Entire House
4 bedrooms, 4 beds, 2 bathrooms
8–13 Nov
4.98 out of 5 average rating, 87 reviews
Top guest favourite
Home in Libertyville
Modern French Escape | Near Base
4 bedrooms, 5 beds, 2.5 bathrooms
19–24 Sept
4.97 out of 5 average rating, 60 reviews
Top guest favourite
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, 134 reviews
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
Top guest favourite
Home in Highland Park
6 bed pool Indoor Basketball Gym
6 bedrooms, 6 beds, 6.5 bathrooms
19–26 Dec
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in North Chicago
Modern 4 BR 3 miles from Great Lakes Naval Base
4 bedrooms, 5 beds, 1.5 bathrooms
25–30 Sept
5.0 out of 5 average rating, 27 reviews
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
Home in North Chicago
4BR Retreat/Sauna near Great Lakes Naval Base
4 bedrooms, 5 beds, 2 bathrooms
30 Oct – 4 Nov
New place to stay
Top guest favourite
Home in Waukegan
Kalo House | Mid-Century Modern Retreat
4 bedrooms, 4 beds, 2 bathrooms
18–23 Oct
5.0 out of 5 average rating, 20 reviews
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, 155 reviews