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Search results; Over 1,000 homes in Highland Park

Top guest favourite
Guest suite in Highland Park
Charming space w/ use of deck and yard
1 bedroom, 2 beds, 1 private bathroom
28 Sept – 3 Oct
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4.97 out of 5 average rating, 166 reviews
Top guest favourite
Cottage in Highland Park
Re-imagined 1880s cottage by Highwood, Metra, Lake
2 bedrooms, 4 beds
19–24 Sept
4.98 out of 5 average rating, 109 reviews
Guest favourite
Home in Highland Park
Cozy 2-Bedroom Cottage Near Downtown Highland Park
2 bedrooms, 2 queen beds
7–12 Sept
4.94 out of 5 average rating, 183 reviews
Top guest favourite
Home in Highland Park
5 min to Ravinia*Navy Base*Sleeps 7*Smart TVs
3 bedrooms, 4 beds
7–12 Sept
4.95 out of 5 average rating, 21 reviews
Top guest favourite
Home in Highland Park
North Shore - Home Away From Home
4 bedrooms, 5 beds
21–26 Sept
5.0 out of 5 average rating, 44 reviews
Guest favourite
Flat in Highwood
Cozy Highwood Apt 4 BR 2 train stops to Naval Base
4 bedrooms, 5 beds
1–6 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Highland Park
North Shore Blue-Door Bungalow
3 bedrooms, 4 beds
15–20 Sept
4.94 out of 5 average rating, 47 reviews
Flat in Highwood
Cozy 2 bed Apt- 2 train stops to the Naval Base!
2 bedrooms, 5 beds
7–12 Sept
4.75 out of 5 average rating, 16 reviews
Top guest favourite
Home in Northbrook
*King bed *Outdoor Living *Sought-After Area
3 bedrooms, 3 beds
13–18 Oct
4.98 out of 5 average rating, 131 reviews
Top guest favourite
Cottage in Highwood
The Pleasant Hill Cottage North Shore Enchantment
3 bedrooms, 6 beds
7–12 Sept
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Guest suite in Riverwoods
Master qtr close to nature & easy urban facilities
1 bedroom, 2 beds
24–29 Oct
4.95 out of 5 average rating, 504 reviews
Guest favourite
Guest house in Lake Forest
Designer's Dream in the North Shore!
1 bedroom, 2 beds
6–11 Sept
4.81 out of 5 average rating, 126 reviews
Room in Highland Park
Priceless split leveranch
1–6 Sept
New place to stay
Top guest favourite
Flat in Wilmette
The Shop - Trendy Studio in the heart of Wilmette
1 bedroom, 1 bed
6–11 Sept
4.94 out of 5 average rating, 64 reviews
Guest favourite
Home in Deerfield
Lake Forest Country Estate
2 bedrooms, 2 beds
1–6 Sept
4.98 out of 5 average rating, 52 reviews
Top guest favourite
Home in Lake Bluff
Home Sweet Home, minutes to Great Lakes Naval Base
3 bedrooms, 4 beds
28 Sept – 3 Oct
4.95 out of 5 average rating, 191 reviews
Guest favourite
Flat in Waukegan
Charming apartment downtown |4.8mi from Navy Base
1 bedroom, 2 beds
11–16 Sept
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in Northbrook
1 Mi to Metra: Estate w/ Theater, Game Room & More
4 bedrooms, 4 beds
1–6 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Room in Wilmette
(BR#1) Welcoming, warm & comfortable, 3 guests
2 beds
21–26 Sept
4.95 out of 5 average rating, 309 reviews