filters

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
,
5.0 out of 5 average rating, 10 reviews
Flat in Highwood
Cozy 2 bed Apt- 2 train stops to the Naval Base!
4.71 out of 5 average rating, 14 reviews, 2 bedrooms, 5 beds, 1 bathroom
7–12 Jul
Top guest favourite
Guest suite in Highland Park
Charming space w/ use of deck and yard
4.97 out of 5 average rating, 162 reviews, 1 bedroom, 2 beds, 1 bathroom
19–24 Jul
Top guest favourite
Cottage in Highland Park
Re-imagined 1880s cottage by Highwood, Metra, Lake
4.98 out of 5 average rating, 105 reviews, 2 bedrooms, 4 beds, 1 bathroom
3–10 Aug
Guest favourite
Flat in Highland Park
Lovely studio near the beach! (and heated floors!)
4.92 out of 5 average rating, 202 reviews, 1 bedroom, 1 bed, 1 bathroom
13–18 Jul
Guest favourite
Home in Highland Park
Cozy 2-Bedroom Cottage Near Downtown Highland Park
4.94 out of 5 average rating, 173 reviews, 2 bedrooms, 2 beds, 1 bathroom
3–8 Aug
Top guest favourite
Guest suite in Riverwoods
Master qtr close to nature & easy urban facilities
4.95 out of 5 average rating, 487 reviews, 1 bedroom, 2 beds, 1 bathroom
11–16 Sept
Top guest favourite
Home in Highland Park
North Shore - Home Away From Home
5.0 out of 5 average rating, 41 reviews, 4 bedrooms, 5 beds, 2 bathrooms
26–31 Aug
Top guest favourite
Home in Northbrook
*King bed *Outdoor Living *Sought-After Area
4.98 out of 5 average rating, 126 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
31 Aug – 5 Sept
Top guest favourite
Home in Highland Park
North Shore Blue-Door Bungalow
4.93 out of 5 average rating, 46 reviews, 3 bedrooms, 4 beds, 1 bathroom
11–16 Jul
Top guest favourite
Home in Lake Bluff
Home Sweet Home, minutes to Great Lakes Naval Base
4.95 out of 5 average rating, 186 reviews, 3 bedrooms, 4 beds, 1 bathroom
5–10 Sept
Guest favourite
Home in Highland Park
Bohemian Bungalow - Highland Park & Highwood
4.95 out of 5 average rating, 20 reviews, 3 bedrooms, 3 beds, 1 bathroom
11–16 Jul
Guest favourite
Room in Highland Park
Perfect for Individual Travelers #2
4.88 out of 5 average rating, 49 reviews, 1 double bed, 1 bathroom
16–21 Jul
Guest favourite
Home in Des Plains
Modern Cozy Retreat by O’Hare
4.94 out of 5 average rating, 17 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
3–8 Aug
Top guest favourite
Flat in Beach Park
J’s Farmhouse Cottage. 2 bedroom duplex.
4.97 out of 5 average rating, 454 reviews, 2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
Top guest favourite
Home in Lake Forest
Spacious Home-Great Lakes Close-Quiet Location
5.0 out of 5 average rating, 31 reviews, 5 bedrooms, 5 beds, 4 bathrooms
10–15 Aug
Flat in Chicago
Northside Chicago Apartment
New place to stay, 2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
Guest favourite
Home in Deerfield
Lake Forest Country Estate
4.98 out of 5 average rating, 47 reviews, 2 bedrooms, 2 beds, 2 bathrooms
7–12 Jul
Top guest favourite
Home in North Chicago
J&J Vacay “Your Navy Graduation Destination”
4.98 out of 5 average rating, 57 reviews, 4 bedrooms, 6 beds, 2.5 bathrooms
19–24 Jul