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Search results; Over 1,000 homes in Highwood

Guest favourite
Flat in Highwood
Cozy Highwood Apt 4 BR 2 train stops to Naval Base
4 bedrooms, 5 beds, 1 private bathroom
1–6 Sept
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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
4.71 out of 5 average rating, 17 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 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, 112 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
Room in Highland Park
Priceless split leveranch
WC
1–6 Sept
New place to stay
Guest favourite
Flat in Highland Park
Lovely studio near the beach! (and heated floors!)
1 bedroom, 1 queen bed, 1 bathroom
10–15 Sept
4.92 out of 5 average rating, 205 reviews
Guest favourite
Home in Northbrook
1 Mi to Metra: Estate w/ Theater, Game Room & More
4 bedrooms, 4 beds, 7 bathrooms
1–6 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Guest suite in Riverwoods
Master qtr close to nature & easy urban facilities
1 bedroom, 2 beds, 1 bathroom
6–11 Sept
4.95 out of 5 average rating, 505 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
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
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 Glenview
Charming Entire House
4 bedrooms, 4 beds, 2 bathrooms
8–13 Nov
4.98 out of 5 average rating, 85 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, 191 reviews
Top guest favourite
Flat in Evanston
New 3bd/1.5 bth Apt w/private prkg
3 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
4.92 out of 5 average rating, 203 reviews
Guest favourite
Room in Glenview
Northside home near O’hare &Downtown
2 beds, 1 bathroom
20–25 Sept
4.95 out of 5 average rating, 64 reviews
Guest favourite
Flat in Waukegan
Greenwood Loft & Rooftop
2 bedrooms, 2 beds, 1 bathroom
30 Oct – 4 Nov
4.91 out of 5 average rating, 192 reviews
Guest favourite
Home in Des Plains
Rosemont 4BD2BA house with Pool
4 bedrooms, 5 beds, 2 bathrooms
6–11 Sept
5.0 out of 5 average rating, 27 reviews
Guest favourite
Guest suite in Des Plains
Relaxing Studio Stay
1 bedroom, 1 bed, 1 bathroom
13–18 Sept
4.93 out of 5 average rating, 81 reviews