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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
15–20 Aug
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4.97 out of 5 average rating, 164 reviews
Guest favourite
Home in Highland Park
Cozy 2-Bedroom Cottage Near Downtown Highland Park
2 bedrooms, 2 queen beds, 1 bathroom
22–27 Aug
4.94 out of 5 average rating, 179 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
North Shore - Home Away From Home
4 bedrooms, 5 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 43 reviews
Top guest favourite
Home in Highland Park
5 min to Ravinia*Navy Base*Sleeps 7*Smart TVs
3 bedrooms, 4 beds, 4 bathrooms
16–21 Aug
4.95 out of 5 average rating, 20 reviews
Guest favourite
Flat in Highland Park
Lovely studio near the beach! (and heated floors!)
1 bedroom, 1 queen bed, 1 bathroom
10–15 Sept
4.92 out of 5 average rating, 205 reviews
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
Room in Highland Park
Priceless split leveranch
WC
17–22 Aug
New place to stay
Top guest favourite
Cottage in Highwood
The Pleasant Hill Cottage North Shore Enchantment
3 bedrooms, 6 beds, 2.5 bathrooms
18–23 Aug
5.0 out of 5 average rating, 15 reviews
Flat in Highwood
Cozy 2 bed Apt- 2 train stops to the Naval Base!
2 bedrooms, 5 beds, 1 bathroom
13–18 Aug
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, 1.5 bathrooms
31 Aug – 5 Sept
4.98 out of 5 average rating, 130 reviews
Top guest favourite
Guest suite in Riverwoods
Master qtr close to nature & easy urban facilities
1 bedroom, 2 beds, 1 bathroom
11–16 Sept
4.95 out of 5 average rating, 499 reviews
Superhost
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, 7 reviews
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, 10 reviews
Top guest favourite
Guest house in Evanston
Mr. Hughes’ Attic, an 80s-themed coach house
1 bedroom, 1 queen bed, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 101 reviews
Top guest favourite
Room in Des Plains
Near O'Hare | King Bed+Shared Bathroom+Parking
1 king bed, 1 bathroom
29 Aug – 3 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Guest suite in Northbrook
Elegant 2BR/2BA Northshore Garden Apartment
2 bedrooms, 3 beds, 2 bathrooms
24–29 Aug
4.92 out of 5 average rating, 101 reviews
Top guest favourite
Townhouse in Lake Forest
Furnished Lake Forest 3BR Townhome | Monthly
3 bedrooms, 3 beds, 2.5 bathrooms
22–27 Dec
5.0 out of 5 average rating, 13 reviews
Guest favourite
Flat in Waukegan
Greenwood Loft & Rooftop
2 bedrooms, 2 beds, 1 bathroom
21–26 Sept
4.91 out of 5 average rating, 188 reviews