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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
11–16 Oct
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5.0 out of 5 average rating, 18 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, 115 reviews
Guest favourite
Flat in Highwood
Cozy Highwood Apt 4 BR 2 train stops to Naval Base
4 bedrooms, 5 beds, 1 bathroom
21–26 Sept
5.0 out of 5 average rating, 8 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, 207 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
Guest favourite
Home in Highland Park
Cozy 2-Bedroom Cottage Near Downtown Highland Park
2 bedrooms, 2 queen beds, 1 bathroom
20–25 Sept
4.93 out of 5 average rating, 191 reviews
Top guest favourite
Home in Waukegan
Kalo House | Mid-Century Modern Retreat
4 bedrooms, 4 beds, 2 bathrooms
18–23 Oct
5.0 out of 5 average rating, 19 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 Waukegan
Historical Hideaway near Naval Base
3 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
4.96 out of 5 average rating, 49 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, 87 reviews
Top guest favourite
Home in Arlington Heights
Peaceful Home in AH
3 bedrooms, 3 beds, 2 bathrooms
12–17 Sept
4.97 out of 5 average rating, 37 reviews
Top guest favourite
Home in Beach Park
"Magnolia Farmhouse" inspired 4-bedroom home
4 bedrooms, 5 beds, 2 bathrooms
7–12 Nov
4.96 out of 5 average rating, 360 reviews
Top guest favourite
Home in Des Plains
3bedrooms& 2 bath (king bed) in newly updated Home
4 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.91 out of 5 average rating, 130 reviews
Top guest favourite
Home in Highland Park
North Shore Blue-Door Bungalow
3 bedrooms, 4 beds, 1 bathroom
23–28 Sept
4.94 out of 5 average rating, 47 reviews
Top guest favourite
Home in Gurnee
Cozy & Elegant 2BR | Near Naval Base, Six Flags -2
2 bedrooms, 2 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Home in Waukegan
Navy Graduation Retreat- 4BR Home by Great Lakes
4 bedrooms, 5 beds, 3 bathrooms
12–17 Oct
5.0 out of 5 average rating, 64 reviews
Top guest favourite
Cottage in Barrington
Cozy French Inspired Cottage in rural setting
3 bedrooms, 3 beds, 2 bathrooms
11–16 Sept
4.99 out of 5 average rating, 142 reviews
Top guest favourite
Home in Libertyville
Modern French Escape | Near Base
4 bedrooms, 5 beds, 2.5 bathrooms
19–24 Sept
4.97 out of 5 average rating, 60 reviews
Top guest favourite
Home in Chicago
Big house in the BEST Location!
3 bedrooms, 3 beds, 2.5 bathrooms
19–24 Oct
4.97 out of 5 average rating, 66 reviews