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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, 165 reviews
Guest favourite
Home in Highland Park
Cozy 2-Bedroom Cottage Near Downtown Highland Park
2 bedrooms, 2 queen beds, 1 bathroom
30 Aug – 4 Sept
4.94 out of 5 average rating, 183 reviews
Top guest favourite
Cottage in Highland Park
Re-imagined 1880s cottage by Highwood, Metra, Lake
2 bedrooms, 4 beds, 1 bathroom
19–24 Sept
4.98 out of 5 average rating, 109 reviews
Top guest favourite
Home in Highland Park
5 min to Ravinia*Navy Base*Sleeps 7*Smart TVs
3 bedrooms, 4 beds, 4 bathrooms
7–12 Sept
4.95 out of 5 average rating, 20 reviews
Top guest favourite
Home in Highland Park
North Shore - Home Away From Home
4 bedrooms, 5 beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 44 reviews
Top guest favourite
Home in Highland Park
6 bed pool Indoor Basketball Gym
6 bedrooms, 6 beds, 6.5 bathrooms
20–25 Nov
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Cottage in Highwood
The Pleasant Hill Cottage North Shore Enchantment
3 bedrooms, 6 beds, 2.5 bathrooms
19–24 Aug
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, 1 bathroom
24–29 Oct
4.95 out of 5 average rating, 503 reviews
Flat in Highwood
Cozy 2 bed Apt- 2 train stops to the Naval Base!
2 bedrooms, 5 beds, 1 bathroom
25–30 Aug
4.75 out of 5 average rating, 16 reviews
Room in Highland Park
Priceless split leveranch
WC
19–24 Aug
New place to stay
Top guest favourite
Home in Highland Park
North Shore Blue-Door Bungalow
3 bedrooms, 4 beds, 1 bathroom
15–20 Sept
4.94 out of 5 average rating, 47 reviews
Guest favourite
Flat in Highwood
Cozy Highwood Apt 4 BR 2 train stops to Naval Base
4 bedrooms, 5 beds, 1 bathroom
22–27 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Northbrook
*King bed *Outdoor Living *Sought-After Area
3 bedrooms, 3 beds, 1.5 bathrooms
31 Aug – 5 Sept
4.98 out of 5 average rating, 131 reviews
Top guest favourite
Home in Lake Forest
Spacious Home-Great Lakes Close-Quiet Location
5 bedrooms, 5 beds, 4 bathrooms
19–24 Aug
5.0 out of 5 average rating, 34 reviews
Guest favourite
Room in Glenview
Northside home near O’hare &Downtown
2 beds, 1 bathroom
18–23 Oct
4.95 out of 5 average rating, 64 reviews
Top guest favourite
Home in Glenview
Charming Entire House
4 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
4.98 out of 5 average rating, 85 reviews
Home in Chicago
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
New place to stay
Top guest favourite
Home in Waukegan
Navy Graduation Retreat- 4BR Home by Great Lakes
4 bedrooms, 5 beds, 3 bathrooms
18–23 Oct
5.0 out of 5 average rating, 61 reviews
Guest favourite
Guest house in Lake Forest
Designer's Dream in the North Shore!
1 bedroom, 2 beds, 1 bathroom
2–7 Sept
4.81 out of 5 average rating, 126 reviews