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Guest favorite
Home in Highland Park
2-Acre Highland Park Retreat with Heated Pool ~ 5*
15 guests6 bedrooms6 beds4 baths
Jun 1 – 6
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Jun 1 – 6
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ﺩ.ﺇ28,628 for 5 nights
for 5 nights

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Superhost
Apartment in Highland Park
Chic Studio in Downtown Highland Park near Metra
1 bed
Jun 1 – 6
ﺩ.ﺇ2,044 for 5 nights
for 5 nights
4.86 out of 5 average rating, 107 reviews
Top guest favorite
Apartment in Highland Park
Full Apartment green oasis in law suite
1 queen bed
Jun 2 – 7
ﺩ.ﺇ3,766 for 5 nights
for 5 nights
5.0 out of 5 average rating, 37 reviews
Superhost
Home in Highland Park
BRAND NEW*North Shore*3 BDR*3 Smart TVs
4 beds
Jun 12 – 17
ﺩ.ﺇ10,311 for 5 nights
for 5 nights
Top guest favorite
Home in Highland Park
Charming Ranch-Style Cottage
2 queen beds
Jun 27 – Jul 2
ﺩ.ﺇ5,153 for 5 nights
for 5 nights
4.97 out of 5 average rating, 117 reviews
Top guest favorite
Room in Highland Park
Stay with CrystalBusiness development,
Modern & Private Basement Retreat with Kitchenette
Jul 1 – 6
ﺩ.ﺇ2,880 for 5 nights
for 5 nights
5.0 out of 5 average rating, 61 reviews
Guest favorite
Apartment in Highland Park
Lovely studio near the beach! (and heated floors!)
Free cancellation
Jun 7 – 12
ﺩ.ﺇ3,905 for 5 nights
for 5 nights
4.91 out of 5 average rating, 161 reviews
Guest favorite
Room in Highland Park
Stay with NinaResale shop owner,
Perfect for Individual Travelers #1
Jul 3 – 8
ﺩ.ﺇ1,184 for 5 nights
for 5 nights
4.89 out of 5 average rating, 212 reviews
Top guest favorite
Home in Highland Park
A Wonderful Getaway Home on the North Shore!
Free cancellation
Sep 1 – 6
ﺩ.ﺇ5,101 for 5 nights
for 5 nights
4.91 out of 5 average rating, 67 reviews
Top guest favorite
Guest suite in Highland Park
Charming in-law suite w/ use of deck and yard
2 queen beds
Jun 2 – 7
ﺩ.ﺇ3,595 for 5 nights
for 5 nights
4.97 out of 5 average rating, 144 reviews
Top guest favorite
Cottage in Highland Park
Re-imagined 1880s cottage by Highwood, Metra, Lake
Free cancellation
Sep 1 – 6
ﺩ.ﺇ6,819 for 5 nights
for 5 nights
4.97 out of 5 average rating, 79 reviews
Guest favorite
Home in Highland Park
Witness Sunrise Over Lake Michigan
Free cancellation
Jul 20 – 25
ﺩ.ﺇ24,517 for 5 nights
for 5 nights
4.93 out of 5 average rating, 54 reviews
Guest favorite
Room in Highland Park
Stay with TamaraTeacher,
Redhothens in Ravinia
Jul 6 – 11
ﺩ.ﺇ2,238 for 5 nights
for 5 nights
4.9 out of 5 average rating, 67 reviews
Home in Highland Park
North Shore Chicago Coastal Retreat
Free cancellation
Jul 6 – 11
ﺩ.ﺇ7,727 for 5 nights
for 5 nights
New place to stay
Guest favorite
Home in Highland Park
North Shore - Home Away From Home
Free cancellation
Sep 24 – 29
ﺩ.ﺇ6,781 for 5 nights
for 5 nights
5.0 out of 5 average rating, 6 reviews
Top guest favorite
Home in Highland Park
North Shore Blue-Door Bungalow
Free cancellation
Nov 16 – 21
ﺩ.ﺇ6,712 for 5 nights
for 5 nights
4.93 out of 5 average rating, 29 reviews
Guest suite in Highland Park
Your relaxing stay in Highland Park
1 queen bed
Jun 4 – 9
ﺩ.ﺇ2,492 for 5 nights
for 5 nights
4.79 out of 5 average rating, 152 reviews
Superhost
Home in Highland Park
Rejuvenate and Relax in the North Shore
7 beds
Jun 2 – 7
ﺩ.ﺇ11,012 for 5 nights
for 5 nights
4.9 out of 5 average rating, 126 reviews
Top guest favorite
Guest suite in Riverwoods
Master qtr close to nature & easy urban facilities
Free cancellation
Jul 19 – 24
ﺩ.ﺇ3,551 for 5 nights
for 5 nights
4.96 out of 5 average rating, 397 reviews