House holiday rentals in Highland Park
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Top-rated house rentals in Highland Park
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Highland Park
House rentals with a pool
Home in Grayslake
4.95 out of 5 average rating, 109 reviewsHuge Indoor Pool &Theater - link moved see details
6–13 Dec
Home in Lake Forest
4.91 out of 5 average rating, 58 reviewsBeautiful 137 Year Old Farm Home (3night min)
8–15 Apr
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
23–30 Jan
Home in Grayslake
5.0 out of 5 average rating, 15 reviewsFamily-sized Indoor Heated Pool & Movie Theater!
6–13 Jan
Home in McHenry
5.0 out of 5 average rating, 35 reviewsHighwood Haven
6–13 Jan
Home in Plainfield
4.95 out of 5 average rating, 62 reviewsRelaxing Spanish style Home (w/heated pool)
23–30 Sep
Home in Genoa City
5.0 out of 5 average rating, 34 reviewsFamily Getaway by Lake Geneva - Games Pool & Yard
8–15 Feb
Home in Glen Ellyn
4.94 out of 5 average rating, 16 reviewsGlen Ellyn Home
23–30 Jul
Weekly house rentals
Home in Chicago
4.98 out of 5 average rating, 206 reviewsWrigleyville Southport Studio
28 Nov – 5 Dec
Home in Highland Park
4.98 out of 5 average rating, 59 reviewsCharming Ranch-Style Cottage
16–23 Apr
Home in Lake Forest
5.0 out of 5 average rating, 6 reviewsParkside Cottage Near the Train
24 Feb – 3 Mar
Home in Highland Park
4.86 out of 5 average rating, 43 reviewsA Wonderful Getaway Home on the North Shore!
23 Feb – 2 Mar
Home in Northbrook
5.0 out of 5 average rating, 16 reviewsNorthbrook Retreat with Ample Outdoor Space
10–17 Sep
Home in Deerfield
4.96 out of 5 average rating, 26 reviewsLake Forest Country Estate
21–28 May
Home in Wilmette
4.98 out of 5 average rating, 92 reviewsUnique porcelain-enamel paneled "Lustron" home
29 Sep – 6 Oct
Home in Highland Park
4.8 out of 5 average rating, 30 reviewsModern Luxe Home w/Gameroom and Electric Fireplace
26 Sep – 3 Oct
Private house rentals
Home in Waukegan
4.91 out of 5 average rating, 65 reviewsThe Indigo Cottage
7–14 Jan
Home in North Chicago
4.97 out of 5 average rating, 33 reviewsSpacious 2-br, 1 bath home w/AC near Naval Base
5–12 Dec
Home in Libertyville
5.0 out of 5 average rating, 11 reviewsPrivate Get A Way
5–12 Oct
Home in Antioch
4.96 out of 5 average rating, 27 reviewsHideaway Lakehouse
5–12 May
Home in Evanston
5.0 out of 5 average rating, 55 reviewsLarimer Park Carriage House
6–13 Dec
Home in Arlington Heights
5.0 out of 5 average rating, 18 reviewsSun-filled luxury, walk to AHdowntown, fenced yard
16–23 Feb
Home in Kenosha
5.0 out of 5 average rating, 96 reviewsLITTLE HOUSE by the BIG LAKE
4–11 Apr
Home in Berwyn
5.0 out of 5 average rating, 77 reviewsRetro Modern Bungalow | free parking | fire pit
28 Dec – 4 Jan
Quick stats about house rentals in Highland Park
Total rentals
30 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
1.1K reviews
Nightly prices starting at
€ 37 before taxes and fees
Destinations to explore
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