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Search results; Over 1,000 homes in Highland Park

Guest favourite
Home in Highland Park
Rejuvenate and Relax in the North Shore
4 bedrooms, 5 beds, 2.5 private bathrooms
12–17 Aug
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4.89 out of 5 average rating, 142 reviews
Top guest favourite
Guest suite in Highland Park
Charming space w/ use of deck and yard
1 bedroom, 2 queen beds, 1 bathroom
29 Aug – 3 Sept
4.97 out of 5 average rating, 162 reviews
Guest favourite
Home in Highland Park
Cozy 2-Bedroom Cottage Near Downtown Highland Park
2 bedrooms, 2 queen beds, 1 bathroom
8–13 Aug
4.94 out of 5 average rating, 178 reviews
Top guest favourite
Cottage in Highland Park
Re-imagined 1880s cottage by Highwood, Metra, Lake
2 bedrooms, 4 beds, 1 bathroom
7–12 Sept
4.98 out of 5 average rating, 106 reviews
Guest favourite
Flat in Highland Park
Lovely studio near the beach! (and heated floors!)
1 bedroom, 1 queen bed, 1 bathroom
3–8 Sept
4.92 out of 5 average rating, 203 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, 41 reviews
Top guest favourite
Home in Lake Bluff
Home Sweet Home, minutes to Great Lakes Naval Base
3 bedrooms, 4 beds, 1 bathroom
9–14 Oct
4.95 out of 5 average rating, 188 reviews
Top guest favourite
Home in Highland Park
North Shore Blue-Door Bungalow
3 bedrooms, 4 beds, 1 bathroom
4–9 Sept
4.93 out of 5 average rating, 46 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, 129 reviews
Top guest favourite
Guest suite in Northbrook
Elegant 2BR/2BA Northshore Garden Apartment
2 bedrooms, 3 beds, 2 bathrooms
4–9 Aug
4.92 out of 5 average rating, 100 reviews
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, 12 reviews
Top guest favourite
Guest suite in Glenview
Garden Suite with Private Full Bath-Adults Only
1 bedroom, 1 queen bed, 1 bathroom
8–13 Sept
4.9 out of 5 average rating, 397 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
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
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, 491 reviews
Guest favourite
Room in Wilmette
(BR#3) Welcoming, warm & comfortable, 1 guest
1 single bed, 1 bathroom
19–24 Aug
4.92 out of 5 average rating, 111 reviews
Top guest favourite
Room in Evanston
Comfortable Private Room in Owner Occupied Home
1 bed, 1 bathroom
11–16 Aug
4.99 out of 5 average rating, 210 reviews
Top guest favourite
Flat in Wilmette
The Shop - Trendy Studio in the heart of Wilmette
1 bedroom, 1 bed, 1 bathroom
9–14 Aug
4.93 out of 5 average rating, 58 reviews
Top guest favourite
Flat in Chicago
Vintage library museum retreat near CTA brown line
2 bedrooms, 2 beds, 1 bathroom
18–23 Jan
5.0 out of 5 average rating, 37 reviews