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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
25–30 Sept
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4.92 out of 5 average rating, 207 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, 114 reviews
Top guest favourite
Home in Highland Park
North Shore - Home Away From Home
4 bedrooms, 5 beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 44 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
Home in Highland Park
5 min to Ravinia*Navy Base*Sleeps 7*Smart TVs
3 bedrooms, 4 beds, 4 bathrooms
8–13 Oct
4.95 out of 5 average rating, 21 reviews
Top guest favourite
Home in Highland Park
North Shore Blue-Door Bungalow
3 bedrooms, 4 beds, 1 bathroom
15–20 Sept
4.94 out of 5 average rating, 47 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
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
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
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, 8 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
Hotel room in Bannockburn
Standard Suite | La Quinta Deerfield | Indoor Pool
1 bedroom, 1 king bed, 1 bathroom
20–25 Sept
New place to stay
Top guest favourite
Guest suite in Riverwoods
Master qtr close to nature & easy urban facilities
1 bedroom, 2 beds, 1 bathroom
24–29 Oct
4.95 out of 5 average rating, 507 reviews
Top guest favourite
Home in Lake Forest
Spacious Home-Great Lakes Close-Quiet Location
5 bedrooms, 5 beds, 4 bathrooms
24–29 Sept
5.0 out of 5 average rating, 36 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 Lake Bluff
Home Sweet Home, minutes to Great Lakes Naval Base
3 bedrooms, 4 beds, 1 bathroom
3–8 Oct
4.95 out of 5 average rating, 195 reviews
Guest favourite
Home in North Chicago
J&J Vacay “Your Navy Graduation Destination”
4 bedrooms, 6 beds, 2.5 bathrooms
16–21 Oct
4.97 out of 5 average rating, 64 reviews
Guest favourite
Guest house in Lake Forest
Designer's Dream in the North Shore!
1 bedroom, 2 beds, 1 bathroom
20–25 Oct
4.81 out of 5 average rating, 127 reviews
Guest favourite
Home in Northbrook
1 Mi to Metra: Estate w/ Theater, Game Room & More
4 bedrooms, 4 beds, 7 bathrooms
11–16 Sept
5.0 out of 5 average rating, 5 reviews