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Search results; Over 1,000 homes in Highwood

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Top guest favourite
Cottage in Highwood
The Pleasant Hill Cottage North Shore Enchantment
3 bedrooms, 6 beds, 2.5 private bathrooms
7–12 Sept
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5.0 out of 5 average rating, 17 reviews
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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, 113 reviews
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Flat in Highwood
Cozy Highwood Apt 4 BR 2 train stops to Naval Base
4 bedrooms, 5 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 8 reviews
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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
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Top guest favourite
Home in Highland Park
Cozy 2-Bedroom Cottage Near Downtown Highland Park
2 bedrooms, 2 queen beds, 1 bathroom
7–12 Sept
4.94 out of 5 average rating, 186 reviews
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Top guest favourite
Home in Highland Park
5 min to Ravinia*Navy Base*Sleeps 7*Smart TVs
3 bedrooms, 4 beds, 4 bathrooms
7–12 Sept
4.95 out of 5 average rating, 21 reviews
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Hotel room in Bannockburn
Exec King Suite | La Quinta Deerfield | Pool Day
1 bedroom, 2 beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 3 reviews
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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
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Home in Highland Park
6 bed pool Indoor Basketball Gym
6 bedrooms, 6 beds, 6.5 bathrooms
20–25 Nov
5.0 out of 5 average rating, 11 reviews
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Room in Highland Park
Priceless split leveranch
WC
1–6 Sept
New place to stay
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Top guest favourite
Home in Highland Park
North Shore Blue-Door Bungalow
3 bedrooms, 4 beds, 1 bathroom
15–20 Sept
4.94 out of 5 average rating, 47 reviews
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Home in Northbrook
1 Mi to Metra: Estate w/ Theater, Game Room & More
4 bedrooms, 4 beds, 7 bathrooms
1–6 Sept
5.0 out of 5 average rating, 5 reviews
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Home in North Chicago
J&J Vacay “Your Navy Graduation Destination”
4 bedrooms, 6 beds, 2.5 bathrooms
18–23 Oct
4.97 out of 5 average rating, 62 reviews
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Home in Lake Forest
Spacious Home-Great Lakes Close-Quiet Location
5 bedrooms, 5 beds, 4 bathrooms
23–28 Sept
5.0 out of 5 average rating, 35 reviews
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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, 132 reviews
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Home in North Chicago
4BR Retreat/Sauna near Great Lakes Naval Base
4 bedrooms, 5 beds, 2 bathrooms
24–29 Oct
New place to stay
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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, 192 reviews
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Flat in Waukegan
Greenwood Loft & Rooftop
2 bedrooms, 2 beds, 1 bathroom
26–31 Oct
4.91 out of 5 average rating, 193 reviews
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Guest favourite
Home in Northbrook
6 Kings | Ping-Pong | Gazebo!
5 bedrooms, 6 king beds, 3.5 bathrooms
27 Sept – 2 Oct
4.9 out of 5 average rating, 52 reviews