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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, 11 reviews
Top guest favourite
Cottage in Highland Park
Re-imagined 1880s cottage by Highwood, Metra, Lake
2 bedrooms, 4 beds
3–10 Aug
4.98 out of 5 average rating, 105 reviews
Top guest favourite
Guest suite in Highland Park
Charming space w/ use of deck and yard
1 bedroom, 2 queen beds
19–24 Jul
4.97 out of 5 average rating, 162 reviews
Flat in Highwood
Cozy 2 bed Apt- 2 train stops to the Naval Base!
2 bedrooms, 5 beds
22–27 Jul
4.71 out of 5 average rating, 14 reviews
Guest favourite
Home in Highland Park
Cozy 2-Bedroom Cottage Near Downtown Highland Park
2 bedrooms, 2 queen beds
3–8 Aug
4.94 out of 5 average rating, 173 reviews
Top guest favourite
Guest suite in Riverwoods
Master qtr close to nature & easy urban facilities
1 bedroom, 2 beds
11–16 Sept
4.95 out of 5 average rating, 487 reviews
Guest favourite
Flat in Highland Park
Lovely studio near the beach! (and heated floors!)
1 bedroom, 1 queen bed
31 Aug – 5 Sept
4.92 out of 5 average rating, 202 reviews
Top guest favourite
Home in Highland Park
North Shore - Home Away From Home
4 bedrooms, 5 beds
26–31 Aug
5.0 out of 5 average rating, 41 reviews
Top guest favourite
Home in Highland Park
North Shore Blue-Door Bungalow
3 bedrooms, 4 beds
12–17 Jul
4.93 out of 5 average rating, 46 reviews
Top guest favourite
Home in Lake Bluff
Home Sweet Home, minutes to Great Lakes Naval Base
3 bedrooms, 4 beds
20–25 Sept
4.95 out of 5 average rating, 187 reviews
Top guest favourite
Home in Northbrook
*King bed *Outdoor Living *Sought-After Area
3 bedrooms, 3 beds
31 Aug – 5 Sept
4.98 out of 5 average rating, 126 reviews
Guest favourite
Guest house in Lake Forest
Designer's Dream in the North Shore!
1 bedroom, 2 beds
17–22 Aug
4.81 out of 5 average rating, 125 reviews
Top guest favourite
Home in Highland Park
5 min to Ravinia*Navy Base*Sleeps 7*Smart TVs
3 bedrooms, 4 beds
16–21 Aug
4.95 out of 5 average rating, 20 reviews
Guest favourite
Home in Highland Park
6 bed pool Indoor Basketball Gym
6 bedrooms, 6 beds
19–24 Dec
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Lake Forest
Spacious Home-Great Lakes Close-Quiet Location
5 bedrooms, 5 beds
10–15 Aug
5.0 out of 5 average rating, 31 reviews
Top guest favourite
Home in Gurnee
Cozy & Elegant 2BR | Near Naval Base and Six Flags
2 bedrooms
4–9 Aug
5.0 out of 5 average rating, 23 reviews
Guest favourite
Home in Deerfield
Lake Forest Country Estate
2 bedrooms, 2 beds
19–24 Jul
4.98 out of 5 average rating, 47 reviews
Flat in Chicago
Northside Chicago Apartment
2 bedrooms, 2 beds
29 Sept – 4 Oct
New place to stay
Top guest favourite
Home in Round Lake Beach
Round Lake Getaway Retreat
2 bedrooms, 4 beds
10–15 Jan
5.0 out of 5 average rating, 204 reviews