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Search results; Over 1,000 homes in Highwood

Top guest favourite
Cottage in Highwood
The Pleasant Hill Cottage North Shore Enchantment
3 bedrooms, 6 beds, 2.5 private bathrooms
9–14 Jul
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5.0 out of 5 average rating, 9 reviews
Flat in Highwood
Cozy 2 bed Apt- 2 train stops to the Naval Base!
2 bedrooms, 5 beds
6–11 Jul
4.71 out of 5 average rating, 14 reviews
Top guest favourite
Guest suite in Highland Park
Charming space w/ use of deck and yard
1 bedroom, 2 queen beds
18–23 Jul
4.97 out of 5 average rating, 161 reviews
Top guest favourite
Cottage in Highland Park
Re-imagined 1880s cottage by Highwood, Metra, Lake
2 bedrooms, 4 beds
3–10 Aug
4.98 out of 5 average rating, 105 reviews
Guest favourite
Flat in Highland Park
Lovely studio near the beach! (and heated floors!)
1 bedroom, 1 queen bed
13–18 Jul
4.92 out of 5 average rating, 202 reviews
Guest favourite
Home in Highland Park
Cozy 2-Bedroom Cottage Near Downtown Highland Park
2 bedrooms, 2 queen beds
6–11 Jul
4.94 out of 5 average rating, 173 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, 485 reviews
Top guest favourite
Home in Highland Park
North Shore - Home Away From Home
4 bedrooms, 5 beds
26–31 Aug
5.0 out of 5 average rating, 41 reviews
Superhost
Flat in Highwood
Highwood Haven- 4 Bed 2 train stops to Naval Base!
4 bedrooms, 5 beds
13–18 Aug
4.8 out of 5 average rating, 5 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, 125 reviews
Top guest favourite
Home in Lake Bluff
Home Sweet Home, minutes to Great Lakes Naval Base
3 bedrooms, 4 beds
5–10 Sept
4.95 out of 5 average rating, 185 reviews
Home in Riverwoods
Riverwoods Nature Retreat
3 bedrooms, 4 beds
18–23 Dec
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, 31 reviews
Top guest favourite
Home in Highland Park
North Shore Blue-Door Bungalow
3 bedrooms, 4 beds
11–16 Jul
4.93 out of 5 average rating, 46 reviews
Guest favourite
Home in Highland Park
Bohemian Bungalow - Highland Park & Highwood
3 bedrooms, 3 beds
11–16 Jul
4.95 out of 5 average rating, 20 reviews
Guest favourite
Room in Wilmette
(BR#1) Welcoming, warm & comfortable, 3 guests
2 beds
14–19 Aug
4.95 out of 5 average rating, 301 reviews
Guest favourite
Home in Waukegan
Luxury 4BR near Six Flags & Naval Base
4 bedrooms, 4 queen beds
19–24 Jul
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Home in Glenview
Charming Entire House
4 bedrooms, 4 beds
30 Aug – 4 Sept
4.99 out of 5 average rating, 77 reviews
Flat in Chicago
Northside Chicago Apartment
2 bedrooms, 2 beds
7–12 Sept
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