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Search results; Over 1,000 homes in Highland Park

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Guest suite in Highland Park
Your relaxing stay in Highland Park
1 bedroom, 1 bed, 1 private bathroom
11–16 Sept
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4.77 out of 5 average rating, 197 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, 109 reviews
Guest favourite
Home in Highland Park
Cozy 2-Bedroom Cottage Near Downtown Highland Park
2 bedrooms, 2 queen beds, 1 bathroom
7–12 Sept
4.94 out of 5 average rating, 183 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
Top guest favourite
Home in Highland Park
5 min to Ravinia*Navy Base*Sleeps 7*Smart TVs
3 bedrooms, 4 beds, 4 bathrooms
7–12 Sept
4.95 out of 5 average rating, 21 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
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
Guest favourite
Flat in Highwood
Cozy Highwood Apt 4 BR 2 train stops to Naval Base
4 bedrooms, 5 beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 8 reviews
Flat in Highwood
Cozy 2 bed Apt- 2 train stops to the Naval Base!
2 bedrooms, 5 beds, 1 bathroom
7–12 Sept
4.75 out of 5 average rating, 16 reviews
Top guest favourite
Cottage in Highwood
The Pleasant Hill Cottage North Shore Enchantment
3 bedrooms, 6 beds, 2.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 16 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, 131 reviews
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, 504 reviews
Guest favourite
Guest house in Lake Forest
Designer's Dream in the North Shore!
1 bedroom, 2 beds, 1 bathroom
6–11 Sept
4.81 out of 5 average rating, 126 reviews
Room in Highland Park
Priceless split leveranch
WC
1–6 Sept
New place to stay
Top guest favourite
Flat in Wilmette
The Shop - Trendy Studio in the heart of Wilmette
1 bedroom, 1 bed, 1 bathroom
6–11 Sept
4.94 out of 5 average rating, 64 reviews
Guest favourite
Flat in Waukegan
Charming apartment downtown |4.8mi from Navy Base
1 bedroom, 2 beds, 1 bathroom
11–16 Sept
5.0 out of 5 average rating, 11 reviews
Room in Des Plains
Lake View Private Room Near O’Hare & Chicago
1 bed, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Lake Bluff
Home Sweet Home, minutes to Great Lakes Naval Base
3 bedrooms, 4 beds, 1 bathroom
28 Sept – 3 Oct
4.95 out of 5 average rating, 191 reviews
Top guest favourite
Room in Mundelein
PRIVATE Room in a beautiful luxury home
1 bed, 1 bathroom
4–9 Sept
4.96 out of 5 average rating, 47 reviews