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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
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
6 bed pool Indoor Basketball Gym
6 bedrooms, 6 beds, 6.5 bathrooms
19–26 Dec
5.0 out of 5 average rating, 11 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
North Shore - Home Away From Home
4 bedrooms, 5 beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 44 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
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
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 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 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
Flat in Evanston
New 3bd/1.5 bth Apt w/private prkg
3 bedrooms, 4 beds, 2 bathrooms
18–23 Oct
4.92 out of 5 average rating, 211 reviews
Top guest favourite
Guest suite in Riverwoods
Master qtr close to nature & easy urban facilities
1 bedroom, 2 beds, 1 bathroom
24–29 Oct
4.95 out of 5 average rating, 507 reviews
Top guest favourite
Home in North Chicago
Guest Favorite | Navy PIR Family Retreat Sleeps 9
4 bedrooms, 5 beds, 2 bathrooms
3–8 Oct
5.0 out of 5 average rating, 74 reviews
Top guest favourite
Home in Gurnee
Gurnee Gathering Place Near Navy Base
4 bedrooms, 4 beds, 2.5 bathrooms
26 Sept – 1 Oct
4.98 out of 5 average rating, 120 reviews
Guest favourite
Home in Northbrook
1 Mi to Metra: Estate w/ Theater, Game Room & More
4 bedrooms, 4 beds, 7 bathrooms
12–17 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Wauconda
Modern 4BR Lake Retreat • Walk to Beach & Main St
4 bedrooms, 4 beds, 1.5 bathrooms
24–29 Oct
4.99 out of 5 average rating, 82 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