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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
26–31 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!
4.71 out of 5 average rating, 14 reviews, 2 bedrooms, 5 beds, 1 bathroom
6–11 Jul
Top guest favourite
Cottage in Highland Park
Re-imagined 1880s cottage by Highwood, Metra, Lake
4.98 out of 5 average rating, 105 reviews, 2 bedrooms, 4 beds, 1 bathroom
3–10 Aug
Top guest favourite
Guest suite in Highland Park
Charming space w/ use of deck and yard
4.97 out of 5 average rating, 161 reviews, 1 bedroom, 2 beds, 1 bathroom
18–23 Jul
Superhost
Flat in Highwood
Highwood Haven- 4 Bed 2 train stops to Naval Base!
4.8 out of 5 average rating, 5 reviews, 4 bedrooms, 5 beds, 2 bathrooms
13–18 Aug
Guest favourite
Home in Highland Park
Cozy 2-Bedroom Cottage Near Downtown Highland Park
4.94 out of 5 average rating, 173 reviews, 2 bedrooms, 2 beds, 1 bathroom
6–11 Jul
Top guest favourite
Home in Highland Park
North Shore - Home Away From Home
5.0 out of 5 average rating, 41 reviews, 4 bedrooms, 5 beds, 2 bathrooms
26–31 Aug
Top guest favourite
Home in Lake Forest
Spacious Home-Great Lakes Close-Quiet Location
5.0 out of 5 average rating, 31 reviews, 5 bedrooms, 5 beds, 4 bathrooms
10–15 Aug
Guest favourite
Flat in Highland Park
Lovely studio near the beach! (and heated floors!)
4.92 out of 5 average rating, 202 reviews, 1 bedroom, 1 bed, 1 bathroom
13–18 Jul
Top guest favourite
Home in Highland Park
5 min to Ravinia*Navy Base*Sleeps 7*Smart TVs
4.95 out of 5 average rating, 20 reviews, 3 bedrooms, 4 beds, 4 bathrooms
16–21 Aug
Top guest favourite
Home in Lake Bluff
Home Sweet Home, minutes to Great Lakes Naval Base
4.95 out of 5 average rating, 185 reviews, 3 bedrooms, 4 beds, 1 bathroom
5–10 Sept
Top guest favourite
Home in Northbrook
*King bed *Outdoor Living *Sought-After Area
4.98 out of 5 average rating, 125 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
31 Aug – 5 Sept
Top guest favourite
Home in Highland Park
North Shore Blue-Door Bungalow
4.93 out of 5 average rating, 46 reviews, 3 bedrooms, 4 beds, 1 bathroom
11–16 Jul
Top guest favourite
Home in North Chicago
J&J Vacay “Your Navy Graduation Destination”
4.98 out of 5 average rating, 57 reviews, 4 bedrooms, 6 beds, 2.5 bathrooms
19–24 Jul
Superhost
Home in North Chicago
Modern Home Getaway | 4 BED 2 Bath
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 5 beds, 2 bathrooms
12–17 Jul
Top guest favourite
Guest suite in Riverwoods
Master qtr close to nature & easy urban facilities
4.95 out of 5 average rating, 485 reviews, 1 bedroom, 2 beds, 1 bathroom
11–16 Sept
Guest favourite
Home in Northbrook
*King beds*Modern* Renovated*North Shore
4.78 out of 5 average rating, 9 reviews, 4 bedrooms, 4 beds, 2.5 bathrooms
9–14 Jul
Guest favourite
Home in Highland Park
Bohemian Bungalow - Highland Park & Highwood
4.95 out of 5 average rating, 20 reviews, 3 bedrooms, 3 beds, 1 bathroom
11–16 Jul
Top guest favourite
Home in Des Plains
Luxury 4 Bed 2.5 Bath near Chicago O'Hare Airport
4.88 out of 5 average rating, 144 reviews, 4 bedrooms, 4 beds, 2.5 bathrooms
9–14 Aug