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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, 9 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
Home in Highland Park
North Shore - Home Away From Home
4 bedrooms, 5 beds, 2 bathrooms
21–26 Sept
4.98 out of 5 average rating, 45 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 Highland Park
6 bed pool Indoor Basketball Gym
6 bedrooms, 6 beds, 6.5 bathrooms
28 Dec – 4 Jan
5.0 out of 5 average rating, 11 reviews
Hotel room in Bannockburn
Exec King Suite | La Quinta Deerfield | Pool Day
1 bedroom, 2 beds, 1 bathroom
19–24 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Highland Park
5 min to Ravinia*Navy Base*Sleeps 7*Smart TVs
3 bedrooms, 4 beds, 4 bathrooms
8–13 Oct
4.96 out of 5 average rating, 23 reviews
Guest favourite
Home in North Chicago
J&J Vacay “Your Navy Graduation Destination”
4 bedrooms, 6 beds, 2.5 bathrooms
16–21 Oct
4.97 out of 5 average rating, 64 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, 195 reviews
Top guest favourite
Home in Northbrook
*King bed *Outdoor Living *Sought-After Area
3 bedrooms, 3 beds, 1.5 bathrooms
13–18 Oct
4.98 out of 5 average rating, 134 reviews
Top guest favourite
Home in Lake Forest
Spacious Home-Great Lakes Close-Quiet Location
5 bedrooms, 5 beds, 4 bathrooms
24–29 Sept
5.0 out of 5 average rating, 36 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
Superhost
Home in Northbrook
6 Kings | Ping-Pong | Gazebo!
5 bedrooms, 6 king beds, 3.5 bathrooms
27 Sept – 2 Oct
4.87 out of 5 average rating, 53 reviews
Top guest favourite
Flat in Evanston
New 3bd/1.5 bth Apt w/private prkg
3 bedrooms, 4 beds, 2 bathrooms
8–13 Nov
4.92 out of 5 average rating, 212 reviews
Guest favourite
Flat in Waukegan
Greenwood Loft & Rooftop
2 bedrooms, 2 beds, 1 bathroom
8–13 Nov
4.91 out of 5 average rating, 198 reviews
Guest favourite
Home in Northbrook
*King beds*Modern* Renovated*North Shore
4 bedrooms, 4 beds, 2.5 bathrooms
17–22 Sept
4.82 out of 5 average rating, 11 reviews
Guest favourite
Home in Lindenhurst
Peaceful Family & Fur-Friendly home near Navy Base
3 bedrooms, 3 beds, 1 bathroom
18–23 Oct
4.91 out of 5 average rating, 86 reviews