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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
6–11 Jul
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
4–9 Jul
4.97 out of 5 average rating, 161 reviews
Guest favourite
Home in Highland Park
Highland Park Residence
4 bedrooms, 6 beds, 3 bathrooms
9–14 Aug
4.83 out of 5 average rating, 6 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
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, 485 reviews
Guest favourite
Room in Highland Park
Perfect for Individual Travelers #2
1 double bed, 1 bathroom
16–21 Jul
4.88 out of 5 average rating, 48 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, 45 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 Highwood
The Pleasant Hill Cottage North Shore Enchantment
3 bedrooms, 6 beds, 2.5 bathrooms
9–14 Jul
5.0 out of 5 average rating, 9 reviews
Flat in Highwood
Cozy 2 bed Apt- 2 train stops to the Naval Base!
2 bedrooms, 5 beds, 1 bathroom
6–11 Jul
4.71 out of 5 average rating, 14 reviews
Top guest favourite
Home in Northbrook
*King bed *Outdoor Living *Sought-After Area
3 bedrooms, 3 beds, 1.5 bathrooms
9–14 Aug
4.98 out of 5 average rating, 125 reviews
Guest favourite
Home in Highland Park
Bohemian Bungalow - Highwood, Navy Base, & Ravinia
3 bedrooms, 3 beds, 1 bathroom
1–6 Dec
4.95 out of 5 average rating, 20 reviews
Guest favourite
Home in Deerfield
Lake Forest Country Estate
2 bedrooms, 2 beds, 2 bathrooms
6–11 Jul
4.98 out of 5 average rating, 47 reviews
Top guest favourite
Guest suite in Northbrook
Elegant 2BR/2BA Northshore Garden Apartment
2 bedrooms, 3 beds, 2 bathrooms
3–8 Jul
4.92 out of 5 average rating, 99 reviews
Top guest favourite
Home in Lake Bluff
Home Sweet Home, minutes to Great Lakes Naval Base
3 bedrooms, 4 beds, 1 bathroom
6–11 Sept
4.95 out of 5 average rating, 184 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
Flat in Chicago
Northside Chicago Apartment
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
New place to stay