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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
29 Aug – 3 Sept
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4.97 out of 5 average rating, 165 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
Guest favourite
Home in Highland Park
Cozy 2-Bedroom Cottage Near Downtown Highland Park
2 bedrooms, 2 queen beds, 1 bathroom
30 Aug – 4 Sept
4.94 out of 5 average rating, 183 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, 44 reviews
Top guest favourite
Home in Highland Park
5 min to Ravinia*Navy Base*Sleeps 7*Smart TVs
3 bedrooms, 4 beds, 4 bathrooms
7–12 Sept
4.95 out of 5 average rating, 20 reviews
Flat in Highwood
Cozy 2 bed Apt- 2 train stops to the Naval Base!
2 bedrooms, 5 beds, 1 bathroom
20–25 Aug
4.75 out of 5 average rating, 16 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
19–24 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
19–24 Aug
5.0 out of 5 average rating, 16 reviews
Guest favourite
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, 8 reviews
Top guest favourite
Guest suite in Riverwoods
Master qtr close to nature & easy urban facilities
1 bedroom, 2 beds, 1 bathroom
24–29 Oct
4.95 out of 5 average rating, 503 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, 131 reviews
Top 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, 11 reviews
Guest favourite
Room in Glenview
Northside home near O’hare &Downtown
2 beds, 1 bathroom
18–23 Oct
4.95 out of 5 average rating, 64 reviews
Top guest favourite
Home in Arlington Heights
J&D Airbnb
2 bedrooms, 3 beds, 1 bathroom
29 Aug – 3 Sept
4.97 out of 5 average rating, 39 reviews
Top guest favourite
Flat in Beach Park
The Cardinal Nest
2 bedrooms, 3 beds, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 38 reviews
Top guest favourite
Home in Glenview
Charming Entire House
4 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
4.98 out of 5 average rating, 85 reviews
Guest favourite
Guest house in Lake Forest
Designer's Dream in the North Shore!
1 bedroom, 2 beds, 1 bathroom
2–7 Sept
4.81 out of 5 average rating, 126 reviews
Guest favourite
Home in Des Plains
Modern Cozy Retreat by O’Hare
2 bedrooms, 2 beds, 1.5 bathrooms
29 Aug – 3 Sept
4.75 out of 5 average rating, 24 reviews