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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
9–14 Jul
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5.0 out of 5 average rating, 7 reviews
Flat in Highwood
Cozy 2 bed Apt- 2 train stops to the Naval Base!
2 bedrooms, 5 beds, 1 bathroom
6–11 Jul
4.71 out of 5 average rating, 14 reviews
Top guest favourite
Guest suite in Highland Park
Charming space w/ use of deck and yard
1 bedroom, 2 queen beds, 1 bathroom
2–7 Jul
4.97 out of 5 average rating, 161 reviews
Superhost
Flat in Highwood
Highwood Haven- 4 Bed 2 train stops to Naval Base!
4 bedrooms, 5 beds, 2 bathrooms
13–18 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Cottage in Highland Park
Re-imagined 1880s cottage by Highwood, Metra, Lake
2 bedrooms, 4 beds, 1 bathroom
3–10 Aug
4.98 out of 5 average rating, 105 reviews
Guest favourite
Flat in Highland Park
Lovely studio near the beach! (and heated floors!)
1 bedroom, 1 queen bed, 1 bathroom
15–20 Jul
4.92 out of 5 average rating, 202 reviews
Guest favourite
Home in Highland Park
Cozy 2-Bedroom Cottage Near Downtown Highland Park
2 bedrooms, 2 queen beds, 1 bathroom
6–11 Jul
4.94 out of 5 average rating, 171 reviews
Top guest favourite
Home in Highland Park
North Shore - Home Away From Home
4 bedrooms, 5 beds, 2 bathrooms
26–31 Aug
5.0 out of 5 average rating, 41 reviews
Superhost
Home in Schaumburg
Chicagoland-Schaumburg/ORD 3BR Ranch Home, sleeps7
3 bedrooms, 4 beds, 1 bathroom
26–31 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Guest suite in Riverwoods
Master qtr close to nature & easy urban facilities
1 bedroom, 2 beds, 1 bathroom
11–16 Sept
4.95 out of 5 average rating, 482 reviews
Top guest favourite
Home in Northbrook
*King bed *Outdoor Living *Sought-After Area
3 bedrooms, 3 beds, 1.5 bathrooms
9–14 Aug
4.98 out of 5 average rating, 125 reviews
Guest favourite
Room in Highland Park
Perfect for Individual Travelers #2
1 double bed, 1 bathroom
16–21 Jul
4.87 out of 5 average rating, 47 reviews
Top guest favourite
Home in Beach Park
Casa Monarca • 3.5 Bathrooms • Top 1%
3 bedrooms, 7 beds, 3.5 bathrooms
27 Jul – 1 Aug
4.99 out of 5 average rating, 99 reviews
Guest favourite
Flat in Evanston
NEW Fam-Frndly 3 bd 1 bth w/ EZ Parking near NU
3 bedrooms, 1 bathroom
3–8 Jul
4.94 out of 5 average rating, 163 reviews
Guest favourite
Home in Waukegan
Luxury 4BR near Six Flags & Naval Base
4 bedrooms, 4 queen beds, 2 bathrooms
19–24 Jul
5.0 out of 5 average rating, 23 reviews
Home in Riverwoods
Riverwoods Nature Retreat
3 bedrooms, 5 beds, 2.5 bathrooms
1–6 Jul
Top guest favourite
Home in Round Lake Beach
Round Lake Getaway Retreat
2 bedrooms, 4 beds, 1 bathroom
10–15 Jan
5.0 out of 5 average rating, 201 reviews
Top guest favourite
Home in Lake Bluff
Home Sweet Home, minutes to Great Lakes Naval Base
3 bedrooms, 4 beds, 1 bathroom
24–29 Jul
4.95 out of 5 average rating, 183 reviews
Top guest favourite
Home in Highland Park
North Shore Blue-Door Bungalow
3 bedrooms, 4 beds, 1 bathroom
11–16 Jul
4.93 out of 5 average rating, 45 reviews