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Search results; Over 1,000 places

Guest favorite
Home in Highland Park
Charming Ranch-Style Cottage
10 min walk
Apr 29 – May 4
4.98 out of 5 average rating, 58 reviews
Guest favorite
Apartment in Highland Park
Lovely studio near the beach! (and heated floors!)
11 min walk
May 9 – 14
4.94 out of 5 average rating, 122 reviews
Superhost
Apartment in Highland Park
Stunning & Stylish Downtown Studio - Highland Park
13 min walk
May 6 – 11
5.0 out of 5 average rating, 37 reviews
Superhost
Apartment in Highland Park
Chic Studio in Downtown Highland Park near Metra
13 min walk
May 14 – 19
5.0 out of 5 average rating, 60 reviews
Guest favorite
Room in Highland Park
Stylish & comfy private bed, bath, & living room!
13 min walk
Apr 24 – 29
5.0 out of 5 average rating, 40 reviews
Guest favorite
Cottage in Highland Park
Re-imagined 1880s cottage by Highwood, Metra, Lake
3 min drive
May 5 – 10
4.96 out of 5 average rating, 47 reviews
Guest favorite
Room in Highland Park
Perfect for Individual Travelers #1
6 min drive
Apr 25 – 30
4.91 out of 5 average rating, 169 reviews
Guest favorite
Guest suite in Highland Park
Charming in-law suite w/ use of deck and yard
5 min drive
May 9 – 14
4.97 out of 5 average rating, 110 reviews
Superhost
Home in Highland Park
Rejuvenate and Relax in the North Shore
4 min drive
Apr 23 – 28
4.91 out of 5 average rating, 109 reviews
Apartment in Northbrook
Guest Room with 1 King Bed
18 min drive
Apr 18 – 23
4.58 out of 5 average rating, 168 reviews
Guest favorite
Guesthouse in Lake Forest
Adorable Carriage House East Lake Forest
10 min drive
Apr 21 – 26
4.88 out of 5 average rating, 80 reviews
Guest favorite
Guesthouse in Lake Forest
The Green Door - safe and calm with walkability
11 min drive
Aug 9 – 14
4.95 out of 5 average rating, 95 reviews
Guest favorite
Apartment in Highland Park
Full Apartment green oasis in law suite
6 min drive
Apr 27 – May 2
5.0 out of 5 average rating, 12 reviews
Guest favorite
Home in Northbrook
Northbrook Retreat with Ample Outdoor Space
9 min drive
May 4 – 9
5.0 out of 5 average rating, 14 reviews
Apartment in Northbrook
Guest Room with 2 Queen Beds
18 min drive
Apr 18 – 23
4.76 out of 5 average rating, 116 reviews
Superhost
Home in Highland Park
Modern Luxe Home w/Gameroom and Electric Fireplace
6 min drive
Apr 23 – 28
4.82 out of 5 average rating, 28 reviews
Superhost
Home in Highland Park
Witness Sunrise Over Lake Michigan
8 min drive
Apr 19 – 24
4.92 out of 5 average rating, 37 reviews
Superhost
Home in Highland Park
The Sunset Manor - Luxe Mansion for Serene retreat
5 min drive
May 23 – 28
4.88 out of 5 average rating, 8 reviews