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Search results; Over 1,000 homes in Highland Park

Top guest favourite
Home in Highland Park
Cozy 2-Bedroom Cottage Near Downtown Highland Park
2 bedrooms, 2 beds, 1 private bathroom
7–12 Sept
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4.94 out of 5 average rating, 186 reviews
Top guest favourite
Home in Highland Park
North Shore - Home Away From Home
5 beds
21–26 Sept
5.0 out of 5 average rating, 44 reviews
Top guest favourite
Home in Highland Park
5 min to Ravinia*Navy Base*Sleeps 7*Smart TVs
4 beds
7–12 Sept
4.95 out of 5 average rating, 21 reviews
Top guest favourite
Cottage in Highland Park
Re-imagined 1880s cottage by Highwood, Metra, Lake
4 beds
19–24 Sept
4.98 out of 5 average rating, 114 reviews
Top guest favourite
Home in Highland Park
6 bed pool Indoor Basketball Gym
6 beds
20–25 Nov
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Highland Park
North Shore Blue-Door Bungalow
4 beds
15–20 Sept
4.94 out of 5 average rating, 47 reviews
Top guest favourite
Cottage in Highwood
The Pleasant Hill Cottage North Shore Enchantment
6 beds
7–12 Sept
5.0 out of 5 average rating, 17 reviews
Guest favourite
Flat in Highwood
Cozy Highwood Apt 4 BR 2 train stops to Naval Base
5 beds
7–12 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Guest suite in Highland Park
Charming space w/ use of deck and yard
2 queen beds
28 Sept – 3 Oct
4.97 out of 5 average rating, 166 reviews
Top guest favourite
Home in Northbrook
*King bed *Outdoor Living *Sought-After Area
3 beds
13–18 Oct
4.98 out of 5 average rating, 132 reviews
Home in North Chicago
4BR Retreat/Sauna near Great Lakes Naval Base
5 beds
24–29 Oct
New place to stay
Top guest favourite
Home in Lake Forest
Spacious Home-Great Lakes Close-Quiet Location
5 beds
23–28 Sept
5.0 out of 5 average rating, 35 reviews
Hotel room in Bannockburn
Exec King Suite | La Quinta Deerfield | Pool Day
2 beds
6–11 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in North Chicago
Gorgeous Home Stay | 4BD 1.5BA
4 queen beds
6–11 Sept
5.0 out of 5 average rating, 77 reviews
Home in Highland Park
Fresh and stylish family home near Lake Michigan
5 beds
3–8 Sept
4.86 out of 5 average rating, 7 reviews
Guest favourite
Home in Northbrook
1 Mi to Metra: Estate w/ Theater, Game Room & More
4 beds
7–12 Sept
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in North Chicago
J&J Vacay “Your Navy Graduation Destination”
6 beds
26 Sept – 1 Oct
4.97 out of 5 average rating, 62 reviews
Top guest favourite
Home in Lake Bluff
Home Sweet Home, minutes to Great Lakes Naval Base
4 beds
3–8 Oct
4.95 out of 5 average rating, 193 reviews
Top guest favourite
Home in Des Plains
5 Star Luxury Stay Near Chicago O'hare Airport,
5 beds
6–11 Sept
4.98 out of 5 average rating, 95 reviews