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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
13–18 Jul
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4.92 out of 5 average rating, 202 reviews
Top guest favourite
Home in Highland Park
North Shore - Home Away From Home
4 bedrooms, 5 beds, 2 bathrooms
26–31 Aug
5.0 out of 5 average rating, 41 reviews
Guest favourite
Home in Highland Park
Cozy 2-Bedroom Cottage Near Downtown Highland Park
2 bedrooms, 2 queen beds, 1 bathroom
3–8 Aug
4.94 out of 5 average rating, 173 reviews
Top guest favourite
Guest suite in Highland Park
Charming space w/ use of deck and yard
1 bedroom, 2 queen beds, 1 bathroom
19–24 Jul
4.97 out of 5 average rating, 162 reviews
Top guest favourite
Home in Highland Park
5 min to Ravinia*Navy Base*Sleeps 7*Smart TVs
3 bedrooms, 4 beds, 4 bathrooms
16–21 Aug
4.95 out of 5 average rating, 20 reviews
Top guest favourite
Cottage in Highland Park
Re-imagined 1880s cottage by Highwood, Metra, Lake
2 bedrooms, 4 beds, 1 bathroom
3–10 Aug
4.98 out of 5 average rating, 105 reviews
Top guest favourite
Home in Highland Park
North Shore Blue-Door Bungalow
3 bedrooms, 4 beds, 1 bathroom
11–16 Jul
4.93 out of 5 average rating, 46 reviews
Top guest favourite
Cottage in Highwood
The Pleasant Hill Cottage North Shore Enchantment
3 bedrooms, 6 beds, 2.5 bathrooms
26–31 Jul
5.0 out of 5 average rating, 10 reviews
Flat in Highwood
Cozy 2 bed Apt- 2 train stops to the Naval Base!
2 bedrooms, 5 beds, 1 bathroom
7–12 Jul
4.71 out of 5 average rating, 14 reviews
Guest favourite
Home in Highland Park
Bohemian Bungalow - Highland Park & Highwood
3 bedrooms, 3 beds, 1 bathroom
11–16 Jul
4.95 out of 5 average rating, 20 reviews
Top guest favourite
Home in Northbrook
*King bed *Outdoor Living *Sought-After Area
3 bedrooms, 3 beds, 1.5 bathrooms
31 Aug – 5 Sept
4.98 out of 5 average rating, 126 reviews
Top guest favourite
Guest suite in Riverwoods
Master qtr close to nature & easy urban facilities
1 bedroom, 2 beds, 1 bathroom
11–16 Sept
4.95 out of 5 average rating, 487 reviews
Guest favourite
Home in Highland Park
6 bed pool Indoor Basketball Gym
6 bedrooms, 6 beds, 6.5 bathrooms
19–24 Dec
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Lake Bluff
Home Sweet Home, minutes to Great Lakes Naval Base
3 bedrooms, 4 beds, 1 bathroom
5–10 Sept
4.95 out of 5 average rating, 186 reviews
Top guest favourite
Guest suite in Northbrook
Elegant 2BR/2BA Northshore Garden Apartment
2 bedrooms, 3 beds, 2 bathrooms
4–9 Aug
4.92 out of 5 average rating, 99 reviews
Top guest favourite
Home in Lake Forest
Spacious Home-Great Lakes Close-Quiet Location
5 bedrooms, 5 beds, 4 bathrooms
10–15 Aug
5.0 out of 5 average rating, 31 reviews
Guest favourite
Home in Deerfield
Lake Forest Country Estate
2 bedrooms, 2 beds, 2 bathrooms
7–12 Jul
4.98 out of 5 average rating, 47 reviews
Top guest favourite
Guest house in Lake Forest
The Green Door - safe and calm with walkability
1 bedroom, 1 queen bed, 1 bathroom
9–14 Sept
4.94 out of 5 average rating, 149 reviews
Flat in Chicago
Northside Chicago Apartment
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
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