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Search results; Over 1,000 homes in Highland Park

Guest favourite
Home in Highland Park
Rejuvenate and Relax in the North Shore
4 bedrooms, 5 beds, 2.5 private bathrooms
12–17 Aug
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4.9 out of 5 average rating, 143 reviews
Guest favourite
Home in Highland Park
Cozy 2-Bedroom Cottage Near Downtown Highland Park
2 bedrooms, 2 queen beds, 1 bathroom
8–13 Aug
4.94 out of 5 average rating, 179 reviews
Top guest favourite
Home in Highland Park
North Shore - Home Away From Home
4 bedrooms, 5 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 42 reviews
Top guest favourite
Guest suite in Highland Park
Charming space w/ use of deck and yard
1 bedroom, 2 queen beds, 1 bathroom
15–20 Aug
4.97 out of 5 average rating, 163 reviews
Top guest favourite
Cottage in Highland Park
Re-imagined 1880s cottage by Highwood, Metra, Lake
2 bedrooms, 4 beds, 1 bathroom
7–12 Sept
4.98 out of 5 average rating, 108 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
Guest favourite
Flat in Highland Park
Lovely studio near the beach! (and heated floors!)
1 bedroom, 1 queen bed, 1 bathroom
25–30 Sept
4.92 out of 5 average rating, 205 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
Superhost
Flat in Highwood
Cozy Highwood Apt 4 BR 2 train stops to Naval Base
4 bedrooms, 5 beds, 1 bathroom
4–9 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Cottage in Highwood
The Pleasant Hill Cottage North Shore Enchantment
3 bedrooms, 6 beds, 2.5 bathrooms
18–23 Aug
5.0 out of 5 average rating, 15 reviews
Flat in Highwood
Cozy 2 bed Apt- 2 train stops to the Naval Base!
2 bedrooms, 5 beds, 1 bathroom
9–14 Aug
4.75 out of 5 average rating, 16 reviews
Top guest favourite
Guest suite in Northbrook
Elegant 2BR/2BA Northshore Garden Apartment
2 bedrooms, 3 beds, 2 bathrooms
24–29 Aug
4.92 out of 5 average rating, 101 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, 494 reviews
Guest favourite
Home in Highland Park
6 bed pool Indoor Basketball Gym
6 bedrooms, 6 beds, 6.5 bathrooms
20–25 Nov
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Northbrook
*King bed *Outdoor Living *Sought-After Area
3 bedrooms, 3 beds, 1.5 bathrooms
31 Aug – 5 Sept
4.98 out of 5 average rating, 130 reviews
Room in Highland Park
Priceless split leveranch
WC
17–22 Aug
New place to stay
Top guest favourite
Home in Lake Bluff
Home Sweet Home, minutes to Great Lakes Naval Base
3 bedrooms, 4 beds, 1 bathroom
17–22 Oct
4.95 out of 5 average rating, 190 reviews
Guest favourite
Home in Highland Park
Bohemian Bungalow - Highland Park & Highwood
3 bedrooms, 3 beds, 1 bathroom
19–24 Sept
4.95 out of 5 average rating, 20 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, 33 reviews