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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
7–12 Aug
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4.77 out of 5 average rating, 194 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
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
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
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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
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
Flat in Highwood
Cozy 2 bed Apt- 2 train stops to the Naval Base!
2 bedrooms, 5 beds, 1 bathroom
9–14 Aug
4.73 out of 5 average rating, 15 reviews
Guest favourite
Room in Wilmette
(BR#3) Welcoming, warm & comfortable, 1 guest
1 single bed, 1 bathroom
19–24 Aug
4.92 out of 5 average rating, 113 reviews
Guest favourite
Flat in Highland Park
Month-to-Month Secure, Charming, Cozy Pied-à-terre
1 queen bed, 1 bathroom
10–17 Aug
4.88 out of 5 average rating, 17 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
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Guest suite in Glenview
Garden Suite with Private Full Bath-Adults Only
1 bedroom, 1 queen bed, 1 bathroom
20–25 Oct
4.9 out of 5 average rating, 397 reviews
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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
Top guest favourite
Room in Mundelein
PRIVATE Room in a beautiful luxury home
1 bed, 1 bathroom
11–16 Aug
4.96 out of 5 average rating, 46 reviews
Top guest favourite
Room in Des Plains
Near O'Hare | King Bed+Shared Bathroom+Parking
1 king bed, 1 bathroom
16–21 Aug
4.86 out of 5 average rating, 14 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
Guest favourite
Shipping container in Evanston
Container home. Walk to NWU and Central Street.
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Room in Wilmette
Queen Bed w/ Private Bath 5 minutes from 94 Expwy
1 queen bed, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 27 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