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Search results; Over 1,000 homes in Highland Park

Guest favourite
Flat in Highland Park
Lovely studio near the beach! (and heated floors!)
1 bedroom, 1 bed, 1 private bathroom
3–8 Sept
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4.92 out of 5 average rating, 203 reviews
Top guest favourite
Guest suite in Highland Park
Charming space w/ use of deck and yard
4.97 out of 5 average rating, 162 reviews, 1 bedroom, 2 beds, 1 bathroom
29 Aug – 3 Sept
Guest favourite
Home in Highland Park
Cozy 2-Bedroom Cottage Near Downtown Highland Park
4.94 out of 5 average rating, 178 reviews, 2 bedrooms, 2 beds, 1 bathroom
8–13 Aug
Top guest favourite
Cottage in Highland Park
Re-imagined 1880s cottage by Highwood, Metra, Lake
4.98 out of 5 average rating, 106 reviews, 2 bedrooms, 4 beds, 1 bathroom
7–12 Sept
Top guest favourite
Home in Highland Park
North Shore - Home Away From Home
5.0 out of 5 average rating, 41 reviews, 4 bedrooms, 5 beds, 2 bathrooms
21–26 Sept
Top guest favourite
Home in Highland Park
North Shore Blue-Door Bungalow
4.93 out of 5 average rating, 46 reviews, 3 bedrooms, 4 beds, 1 bathroom
4–9 Sept
Top guest favourite
Home in Northbrook
*King bed *Outdoor Living *Sought-After Area
4.98 out of 5 average rating, 129 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
31 Aug – 5 Sept
Top guest favourite
Guest suite in Northbrook
Elegant 2BR/2BA Northshore Garden Apartment
4.92 out of 5 average rating, 100 reviews, 2 bedrooms, 3 beds, 2 bathrooms
4–9 Aug
Top guest favourite
Home in Highland Park
5 min to Ravinia*Navy Base*Sleeps 7*Smart TVs
4.95 out of 5 average rating, 20 reviews, 3 bedrooms, 4 beds, 4 bathrooms
16–21 Aug
Top guest favourite
Cottage in Highwood
The Pleasant Hill Cottage North Shore Enchantment
5.0 out of 5 average rating, 13 reviews, 3 bedrooms, 6 beds, 2.5 bathrooms
18–23 Aug
Guest favourite
Flat in Highland Park
Month-to-Month Secure, Charming, Cozy Pied-à-terre
4.88 out of 5 average rating, 17 reviews, 1 bed, 1 bathroom
10–17 Aug
Top guest favourite
Townhouse in Lake Forest
Furnished Lake Forest 3BR Townhome | Monthly
5.0 out of 5 average rating, 13 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
22–27 Dec
Top guest favourite
Guest suite in Riverwoods
Master qtr close to nature & easy urban facilities
4.95 out of 5 average rating, 493 reviews, 1 bedroom, 2 beds, 1 bathroom
11–16 Sept
Top guest favourite
Room in Evanston
Comfortable Private Room in Owner Occupied Home
4.99 out of 5 average rating, 210 reviews, 1 bed, 1 bathroom
11–16 Aug
Top guest favourite
Flat in Wilmette
The Shop - Trendy Studio in the heart of Wilmette
4.93 out of 5 average rating, 58 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Aug
Guest favourite
Room in Wilmette
(BR#3) Welcoming, warm & comfortable, 1 guest
4.92 out of 5 average rating, 111 reviews, 1 single bed, 1 bathroom
19–24 Aug
Top guest favourite
Guest suite in Glenview
Garden Suite with Private Full Bath-Adults Only
4.9 out of 5 average rating, 397 reviews, 1 bedroom, 1 bed, 1 bathroom
8–13 Sept
Guest favourite
Room in Prospect Heights
Lovely room in 2-bedroom apartment
4.97 out of 5 average rating, 94 reviews, 1 double bed, 1.5 bathrooms
11–16 Aug
Room in Des Plains
Near O'Hare | King Bed+Shared Bathroom+Parking
5.0 out of 5 average rating, 6 reviews, 1 king bed, 1 bathroom
9–14 Aug