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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
29 Aug – 3 Sept
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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
30 Aug – 4 Sept
4.94 out of 5 average rating, 183 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
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, 20 reviews
Flat in Highwood
Cozy 2 bed Apt- 2 train stops to the Naval Base!
2 bedrooms, 5 beds
25–30 Aug
4.75 out of 5 average rating, 16 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
Top guest favourite
Cottage in Highwood
The Pleasant Hill Cottage North Shore Enchantment
3 bedrooms, 6 beds
20–25 Aug
5.0 out of 5 average rating, 16 reviews
Guest favourite
Flat in Highwood
Cozy Highwood Apt 4 BR 2 train stops to Naval Base
4 bedrooms, 5 beds
22–27 Aug
5.0 out of 5 average rating, 8 reviews
Room in Highland Park
Priceless split leveranch
20–25 Aug
New place to stay
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, 503 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, 131 reviews
Guest favourite
Room in Glenview
Northside home near O’hare &Downtown
2 beds
18–23 Oct
4.95 out of 5 average rating, 64 reviews
Top guest favourite
Home in Highland Park
6 bed pool Indoor Basketball Gym
6 bedrooms, 6 beds
20–25 Nov
5.0 out of 5 average rating, 11 reviews
Guest favourite
Guest house in Lake Forest
Designer's Dream in the North Shore!
1 bedroom, 2 beds
2–7 Sept
4.81 out of 5 average rating, 126 reviews
Top guest favourite
Home in Glenview
Charming Entire House
4 bedrooms, 4 beds
30 Aug – 4 Sept
4.98 out of 5 average rating, 85 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, 10 reviews
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, 208 reviews
Top guest favourite
Flat in Beach Park
The Cardinal Nest
2 bedrooms, 3 beds
16–21 Nov
5.0 out of 5 average rating, 38 reviews