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Search results; Over 1,000 homes in Highland Park

Top guest favourite
Guest suite in Highland Park
Charming space w/ use of deck and yard
1 bedroom, 2 beds, 1 private bathroom
15–20 Aug
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4.97 out of 5 average rating, 164 reviews
Top guest favourite
Home in Highland Park
North Shore - Home Away From Home
4 bedrooms, 5 beds
1–6 Sept
5.0 out of 5 average rating, 43 reviews
Guest favourite
Home in Highland Park
Cozy 2-Bedroom Cottage Near Downtown Highland Park
2 bedrooms, 2 queen beds
22–27 Aug
4.94 out of 5 average rating, 179 reviews
Top guest favourite
Home in Highland Park
5 min to Ravinia*Navy Base*Sleeps 7*Smart TVs
3 bedrooms, 4 beds
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
19–24 Sept
4.98 out of 5 average rating, 109 reviews
Guest favourite
Flat in Highland Park
Lovely studio near the beach! (and heated floors!)
1 bedroom, 1 queen bed
10–15 Sept
4.92 out of 5 average rating, 205 reviews
Top guest favourite
Guest suite in Riverwoods
Master qtr close to nature & easy urban facilities
1 bedroom, 2 beds
11–16 Sept
4.95 out of 5 average rating, 499 reviews
Flat in Highwood
Cozy 2 bed Apt- 2 train stops to the Naval Base!
2 bedrooms, 5 beds
13–18 Aug
4.75 out of 5 average rating, 16 reviews
Guest favourite
Home in Highland Park
6 bed pool Indoor Basketball Gym
6 bedrooms, 6 beds
20–25 Nov
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Cottage in Highwood
The Pleasant Hill Cottage North Shore Enchantment
3 bedrooms, 6 beds
18–23 Aug
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Home in Northbrook
*King bed *Outdoor Living *Sought-After Area
3 bedrooms, 3 beds
31 Aug – 5 Sept
4.98 out of 5 average rating, 130 reviews
Top guest favourite
Home in Highland Park
North Shore Blue-Door Bungalow
3 bedrooms, 4 beds
15–20 Sept
4.94 out of 5 average rating, 47 reviews
Top guest favourite
Guest suite in Northbrook
Elegant 2BR/2BA Northshore Garden Apartment
2 bedrooms, 3 beds
24–29 Aug
4.92 out of 5 average rating, 101 reviews
Top guest favourite
Home in Lake Bluff
Home Sweet Home, minutes to Great Lakes Naval Base
3 bedrooms, 4 beds
17–22 Oct
4.95 out of 5 average rating, 190 reviews
Room in Highland Park
Priceless split leveranch
17–22 Aug
New place to stay
Superhost
Flat in Highwood
Cozy Highwood Apt 4 BR 2 train stops to Naval Base
4 bedrooms, 5 beds
22–27 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Lake Forest
Spacious Home-Great Lakes Close-Quiet Location
5 bedrooms, 5 beds
10–15 Aug
5.0 out of 5 average rating, 33 reviews
Guest favourite
Home in Highland Park
Quiet Home: Highland Park, Highwood, Lake Michigan
3 bedrooms, 3 beds
19–24 Sept
4.95 out of 5 average rating, 20 reviews
Top guest favourite
Home in North Chicago
Modern 4 BR 3 miles from Great Lakes Naval Base
4 bedrooms, 5 beds
15–20 Aug
5.0 out of 5 average rating, 24 reviews