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Search results; Over 1,000 homes in Highland Park

Guest favourite
Flat in Highland Park
Lovely studio near the beach! (and heated floors!)
1 bedroom, 1 bed, 1 private bathroom
3–8 Sept
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4.92 out of 5 average rating, 203 reviews
Guest favourite
Home in Highland Park
Cozy 2-Bedroom Cottage Near Downtown Highland Park
4.94 out of 5 average rating, 178 reviews, 2 bedrooms, 2 beds, 1 bathroom
8–13 Aug
Top guest favourite
Home in Highland Park
North Shore - Home Away From Home
5.0 out of 5 average rating, 41 reviews, 4 bedrooms, 5 beds, 2 bathrooms
21–26 Sept
Top guest favourite
Home in Highland Park
5 min to Ravinia*Navy Base*Sleeps 7*Smart TVs
4.95 out of 5 average rating, 20 reviews, 3 bedrooms, 4 beds, 4 bathrooms
16–21 Aug
Top guest favourite
Guest suite in Highland Park
Charming space w/ use of deck and yard
4.97 out of 5 average rating, 162 reviews, 1 bedroom, 2 beds, 1 bathroom
29 Aug – 3 Sept
Top guest favourite
Cottage in Highland Park
Re-imagined 1880s cottage by Highwood, Metra, Lake
4.98 out of 5 average rating, 106 reviews, 2 bedrooms, 4 beds, 1 bathroom
7–12 Sept
Top guest favourite
Cottage in Highwood
The Pleasant Hill Cottage North Shore Enchantment
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 6 beds, 2.5 bathrooms
18–23 Aug
Top guest favourite
Home in Highland Park
North Shore Blue-Door Bungalow
4.93 out of 5 average rating, 46 reviews, 3 bedrooms, 4 beds, 1 bathroom
4–9 Sept
Flat in Highwood
Cozy 2 bed Apt- 2 train stops to the Naval Base!
4.71 out of 5 average rating, 14 reviews, 2 bedrooms, 5 beds, 1 bathroom
9–14 Aug
Top guest favourite
Home in Northbrook
*King bed *Outdoor Living *Sought-After Area
4.98 out of 5 average rating, 129 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
31 Aug – 5 Sept
Guest favourite
Home in Highland Park
6 bed pool Indoor Basketball Gym
5.0 out of 5 average rating, 10 reviews, 6 bedrooms, 6 beds, 6.5 bathrooms
20–25 Nov
Top guest favourite
Guest suite in Riverwoods
Master qtr close to nature & easy urban facilities
4.95 out of 5 average rating, 491 reviews, 1 bedroom, 2 beds, 1 bathroom
11–16 Sept
Top guest favourite
Guest suite in Northbrook
Elegant 2BR/2BA Northshore Garden Apartment
4.92 out of 5 average rating, 100 reviews, 2 bedrooms, 3 beds, 2 bathrooms
4–9 Aug
Top guest favourite
Home in Lake Bluff
Home Sweet Home, minutes to Great Lakes Naval Base
4.95 out of 5 average rating, 188 reviews, 3 bedrooms, 4 beds, 1 bathroom
9–14 Oct
Top guest favourite
Home in Lake Forest
Spacious Home-Great Lakes Close-Quiet Location
5.0 out of 5 average rating, 31 reviews, 5 bedrooms, 5 beds, 4 bathrooms
10–15 Aug
Flat in Skokie
Skokie Serenity - 3 queen beds
New place to stay, 3 bedrooms, 3 beds, 2 bathrooms
16–21 Aug
Guest favourite
Home in Highland Park
Bohemian Bungalow - Highland Park & Highwood
4.95 out of 5 average rating, 20 reviews, 3 bedrooms, 3 beds, 1 bathroom
19–24 Sept
Home in Northbrook
1 Mi to Metra: Estate w/ Theater, Game Room & More
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 4 beds, 7 bathrooms
18–23 Aug
Guest favourite
Home in North Chicago
J&J Vacay “Your Navy Graduation Destination”
4.97 out of 5 average rating, 59 reviews, 4 bedrooms, 6 beds, 2.5 bathrooms
20–25 Sept