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Highland Park long stay rentals
Stay a week, a month or longer in a comfortable place all your own
Featured long stay living spaces - Highland Park
Properties highly-rated for stays of 28 nights or longer, with space to feel right at home
Showing deals for:5 Jan - 2 Feb
Image gallery for Stunning & Stylish Downtown Studio - Highland Park
8.08.0 out of 10, Very good, (4 reviews)
Very good
(4 reviews)
Stunning & Stylish Downtown Studio - Highland Park
Highland Park, IL
8% off
Price is NZ$7,369
NZ$7,369
for 28 nights, 1 apartment
NZ$263 per night
includes taxes & fees
Image gallery for Home Sweet Home, minutes to Great Lakes Naval Base
9.49.4 out of 10, Exceptional, (26 reviews)
Exceptional
(26 reviews)
Home Sweet Home, minutes to Great Lakes Naval Base
Lake Bluff, IL
25% off
Price is NZ$5,589
NZ$5,589
for 28 nights, 1 home
NZ$200 per night
includes taxes & fees
Image gallery for Walk to Train: Convenient Skokie Condo!
8.68.6 out of 10, Excellent, (4 reviews)
Excellent
(4 reviews)
Walk to Train: Convenient Skokie Condo!
Skokie, IL
7% off
Price is NZ$7,732
NZ$7,732
for 28 nights, 1 apartment
NZ$276 per night
includes taxes & fees
Image gallery for Re-imagined 1880's cottage walking distance to Highwood, Metra, Lake Michigan
1010 out of 10, Exceptional, (23 reviews)
Exceptional
(23 reviews)
Re-imagined 1880's cottage walking distance to Highwood, Metra, Lake Michigan
Chicago (and vicinity), IL
26% off
Price is NZ$12,391
NZ$12,391
for 28 nights, 1 cottage
NZ$443 per night
includes taxes & fees
Image gallery for Master qtr close to nature & easy urban facilities
9.89.8 out of 10, Exceptional, (67 reviews)
Exceptional
(67 reviews)
Master qtr close to nature & easy urban facilities
Deerfield, IL
18% off
Price is NZ$4,615
NZ$4,615
for 28 nights, 1 home
NZ$165 per night
includes taxes & fees
Image gallery for Beautifully Decorated Ranch, minutes from Lakefront, Beach and Downtown
9.89.8 out of 10, Exceptional, (116 reviews)
Exceptional
(116 reviews)
Beautifully Decorated Ranch, minutes from Lakefront, Beach and Downtown
Lake Forest, IL
15% off
Price is NZ$16,609
NZ$16,609
for 28 nights, 1 home
NZ$593 per night
includes taxes & fees
Image gallery for 3BR Apartment, Split level house, in Waukegan, 7min. to The Naval Base with WiFi
9.49.4 out of 10, Exceptional, (14 reviews)
Exceptional
(14 reviews)
3BR Apartment, Split level house, in Waukegan, 7min. to The Naval Base with WiFi
Waukegan, IL
13% off
Price is NZ$9,296
NZ$9,296
for 28 nights, 1 home
NZ$332 per night
includes taxes & fees
Image gallery for Special Skevanston Space 2mi to Northwestern University & beach
9.09.0 out of 10, Wonderful, (20 reviews)
Wonderful
(20 reviews)
Special Skevanston Space 2mi to Northwestern University & beach
Evanston, IL
17% off
Price is NZ$5,314
NZ$5,314
for 28 nights, 1 apartment
NZ$190 per night
includes taxes & fees
Image gallery for Charming, light-filled 5br Wilmette home
1010 out of 10, Exceptional, (1 review)
Exceptional
(1 review)
Charming, light-filled 5br Wilmette home
Wilmette, IL
26% off
Price is NZ$13,073
NZ$13,073
for 28 nights, 1 home
NZ$467 per night
includes taxes & fees
Image gallery for Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
1010 out of 10, Exceptional, (38 reviews)
Exceptional
(38 reviews)
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
Evanston, IL
12% off
Price is NZ$6,595
NZ$6,595
for 28 nights, 1 apartment
NZ$236 per night
includes taxes & fees
Image gallery for Kitschy House on a Quiet Tree Lined Street in Upscale Evanston Neighborhood
1010 out of 10, Exceptional, (15 reviews)
Exceptional
(15 reviews)
Kitschy House on a Quiet Tree Lined Street in Upscale Evanston Neighborhood
Evanston, IL
25% off
Price is NZ$8,393
NZ$8,393
for 28 nights, 1 home
NZ$300 per night
includes taxes & fees
Image gallery for The NICEST place in Evanston for Families 1500Main
1010 out of 10, Exceptional, (58 reviews)
Exceptional
(58 reviews)
The NICEST place in Evanston for Families 1500Main
Evanston, IL
12% off
Price is NZ$13,666
NZ$13,666
for 28 nights, 1 home
NZ$488 per night
includes taxes & fees
Image gallery for New Your Home Away From Home! - Near Great Lakes Naval Base!!
9.09.0 out of 10, Wonderful, (29 reviews)
Wonderful
(29 reviews)
New Your Home Away From Home! - Near Great Lakes Naval Base!!
North Chicago, IL
9% off
Price is NZ$20,612
NZ$20,612
for 28 nights, 1 home
NZ$736 per night
includes taxes & fees
Image gallery for Unique Apt. in Upscale Evanston with Easy Access to Chicago
9.89.8 out of 10, Exceptional, (71 reviews)
Exceptional
(71 reviews)
Unique Apt. in Upscale Evanston with Easy Access to Chicago
Evanston, IL
24% off
Price is NZ$8,773
NZ$8,773
for 28 nights, 1 apartment
NZ$313 per night
includes taxes & fees
Image gallery for Outstanding Ohare Oasis
8.88.8 out of 10, Excellent, (19 reviews)
Excellent
(19 reviews)
Outstanding Ohare Oasis
Des Plaines, IL
36% off
Price is NZ$14,628
NZ$14,628
for 28 nights, 1 home
NZ$522 per night
includes taxes & fees
Image gallery for Designer Furnished + Game Room | LCP Collection
1010 out of 10, Exceptional, (3 reviews)
Exceptional
(3 reviews)
Designer Furnished + Game Room | LCP Collection
Des Plaines, IL
16% off
Price is NZ$9,593
NZ$9,593
for 28 nights, 1 home
NZ$343 per night
includes taxes & fees
Image gallery for North Chi retreat – Navy, Sauna, Tiki Bar, Games
9.89.8 out of 10, Exceptional, (9 reviews)
Exceptional
(9 reviews)
North Chi retreat – Navy, Sauna, Tiki Bar, Games
North Chicago, IL
8% off
Price is NZ$15,253
NZ$15,253
for 28 nights, 1 home
NZ$545 per night
includes taxes & fees
Image gallery for Mid Century Elegance in Evanston Vintage Apartment.
1010 out of 10, Exceptional, (16 reviews)
Exceptional
(16 reviews)
Mid Century Elegance in Evanston Vintage Apartment.
Evanston, IL
44% off
Price is NZ$9,129
NZ$9,129
for 28 nights, 1 apartment
NZ$326 per night
includes taxes & fees
Image gallery for Cute Ranch House close to town monthly stay
6.06.0 out of 10, (1 review)
(1 review)
Cute Ranch House close to town monthly stay
Deerfield, IL
8% off
Price is NZ$7,997
NZ$7,997
for 28 nights, 1 home
NZ$286 per night
includes taxes & fees
Image gallery for Serene Retreat Awaits You!
9.69.6 out of 10, Exceptional, (48 reviews)
Exceptional
(48 reviews)
Serene Retreat Awaits You!
Highland Park, IL
17% off
Price is NZ$18,663
NZ$18,663
for 28 nights, 1 home
NZ$667 per night
includes taxes & fees
Image gallery for Spacious 4-bedroom house in amazing Des Plaines with WiFi, AC
9.49.4 out of 10, Exceptional, (3 reviews)
Exceptional
(3 reviews)
Spacious 4-bedroom house in amazing Des Plaines with WiFi, AC
Des Plaines, IL
9% off
Price is NZ$19,158
NZ$19,158
for 28 nights, 1 home
NZ$684 per night
includes taxes & fees
Image gallery for Windy City Welcome
9.49.4 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)
Windy City Welcome
Arlington Heights, IL
35% off
Price is NZ$12,568
NZ$12,568
for 28 nights, 1 home
NZ$449 per night
includes taxes & fees
Image gallery for Chicago's Hidden Treasure, "EVANSTON, IL"
9.69.6 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)
Chicago's Hidden Treasure, "EVANSTON, IL"
Evanston, IL
8% off
Price is NZ$10,839
NZ$10,839
for 28 nights, 1 apartment
NZ$387 per night
includes taxes & fees
Image gallery for Huge 4BR w/ Yard | Sleeps 8 | LCP Collection
9.89.8 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)
Huge 4BR w/ Yard | Sleeps 8 | LCP Collection
Des Plaines, IL
15% off
Price is NZ$15,445
NZ$15,445
for 28 nights, 1 home
NZ$552 per night
includes taxes & fees
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value