Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Homes
Homes
NEW
NEW
Experiences
Experiences, new
NEW
NEW
Services
Services, new
Start your search
Location
Homes in Highland Park
Check in / Check out
Any week
Guests
Add guests
Become a host
Help Centre
Become a host
It’s easy to start hosting and earn extra income.
Refer a host
Find a co-host
Log in or sign up
filters
Filters
Price
Type of place
Show map
Search results; Over 1,000 homes in Highland Park
Over 1,000 homes in Highland Park
Guest favourite
Guest favourite
Flat in Highland Park
Lovely studio near the beach! (and heated floors!)
1 bedroom
,
·
1 bed
,
·
1 private bathroom
13–18 Jul
13–18 Jul
$1,317 SGD
Show price breakdown
for 5 nights
$1,317 SGD for 5 nights
,
·
4.92 out of 5 average rating, 202 reviews
4.92 (202)
Top guest favourite
Guest favourite
Home in Highland Park
North Shore - Home Away From Home
5.0 out of 5 average rating, 41 reviews
5.0 (41)
,
·
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
26–31 Aug
26–31 Aug
$3,045 SGD
Show price breakdown
for 5 nights
$3,045 SGD for 5 nights
Top guest favourite
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
4.95 (20)
,
·
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
4 bathrooms
4 bathrooms
16–21 Aug
16–21 Aug
$3,668 SGD
Show price breakdown
for 5 nights
$3,668 SGD for 5 nights
Guest favourite
Guest favourite
Home in Highland Park
Cozy 2-Bedroom Cottage Near Downtown Highland Park
4.94 out of 5 average rating, 173 reviews
4.94 (173)
,
·
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
6–11 Jul
6–11 Jul
$1,783 SGD
Show price breakdown
for 5 nights
$1,783 SGD for 5 nights
Top guest favourite
Guest favourite
Cottage in Highland Park
Re-imagined 1880s cottage by Highwood, Metra, Lake
4.98 out of 5 average rating, 105 reviews
4.98 (105)
,
·
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
3–10 Aug
3–10 Aug
$3,330 SGD
$3,053 SGD
Show price breakdown
for 7 nights
Home in Highland Park
Highland Park Residence
4.83 out of 5 average rating, 6 reviews
4.83 (6)
,
·
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
,
·
3 bathrooms
3 bathrooms
9–14 Aug
9–14 Aug
$3,083 SGD
Show price breakdown
for 5 nights
$3,083 SGD for 5 nights
Top guest favourite
Guest favourite
Cottage in Highwood
The Pleasant Hill Cottage North Shore Enchantment
5.0 out of 5 average rating, 9 reviews
5.0 (9)
,
·
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
2.5 bathrooms
2.5 bathrooms
9–14 Jul
9–14 Jul
$4,949 SGD
$4,528 SGD
Show price breakdown
for 5 nights
Top guest favourite
Guest favourite
Guest suite in Highland Park
Charming space w/ use of deck and yard
4.97 out of 5 average rating, 161 reviews
4.97 (161)
,
·
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
4–9 Jul
4–9 Jul
$1,287 SGD
Show price breakdown
for 5 nights
$1,287 SGD for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Home in Highland Park
North Shore Blue-Door Bungalow
4.93 out of 5 average rating, 46 reviews
4.93 (46)
,
·
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
11–16 Jul
11–16 Jul
$2,715 SGD
Show price breakdown
for 5 nights
$2,715 SGD for 5 nights
Flat in Highwood
Cozy 2 bed Apt- 2 train stops to the Naval Base!
4.71 out of 5 average rating, 14 reviews
4.71 (14)
,
·
2 bedrooms
2 bedrooms
,
·
5 beds
5 beds
,
·
1 bathroom
1 bathroom
6–11 Jul
6–11 Jul
$1,913 SGD
$1,461 SGD
Show price breakdown
for 5 nights
Top guest favourite
Guest favourite
Home in Lake Forest
Spacious Home-Great Lakes Close-Quiet Location
5.0 out of 5 average rating, 31 reviews
5.0 (31)
,
·
5 bedrooms
5 bedrooms
,
·
5 beds
5 beds
,
·
4 bathrooms
4 bathrooms
10–15 Aug
10–15 Aug
$6,335 SGD
Show price breakdown
for 5 nights
$6,335 SGD for 5 nights
Guest favourite
Guest favourite
Room in Highland Park
Perfect for Individual Travelers #2
4.88 out of 5 average rating, 48 reviews
4.88 (48)
,
·
1 double bed
1 double bed
,
·
1 bathroom
1 bathroom
16–21 Jul
16–21 Jul
$488 SGD
Show price breakdown
for 5 nights
$488 SGD for 5 nights
Top guest favourite
Guest favourite
Home in Northbrook
*King bed *Outdoor Living *Sought-After Area
4.98 out of 5 average rating, 125 reviews
4.98 (125)
,
·
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1.5 bathrooms
1.5 bathrooms
9–14 Aug
9–14 Aug
$2,440 SGD
Show price breakdown
for 5 nights
$2,440 SGD for 5 nights
Top guest favourite
Guest favourite
Home in Lake Bluff
Home Sweet Home, minutes to Great Lakes Naval Base
4.95 out of 5 average rating, 185 reviews
4.95 (185)
,
·
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
30 Aug – 4 Sept
30 Aug – 4 Sept
$1,195 SGD
Show price breakdown
for 5 nights
$1,195 SGD for 5 nights
Free cancellation
Guest favourite
Guest favourite
Home in Northbrook
*King beds*Modern* Renovated*North Shore
4.78 out of 5 average rating, 9 reviews
4.78 (9)
,
·
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
2.5 bathrooms
2.5 bathrooms
9–14 Jul
9–14 Jul
$6,038 SGD
$5,328 SGD
Show price breakdown
for 5 nights
Free cancellation
Superhost
Superhost
Flat in Highwood
Highwood Haven- 4 Bed 2 train stops to Naval Base!
5.0 out of 5 average rating, 4 reviews
5.0 (4)
,
·
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
13–18 Aug
13–18 Aug
$3,168 SGD
Show price breakdown
for 5 nights
$3,168 SGD for 5 nights
Top guest favourite
Guest favourite
Guest suite in Riverwoods
Master qtr close to nature & easy urban facilities
4.95 out of 5 average rating, 485 reviews
4.95 (485)
,
·
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
11–16 Sept
11–16 Sept
$1,019 SGD
Show price breakdown
for 5 nights
$1,019 SGD for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Home in North Chicago
Gorgeous Home Stay | 4BD 1.5BA
5.0 out of 5 average rating, 72 reviews
5.0 (72)
,
·
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
1.5 bathrooms
1.5 bathrooms
7–12 Jul
7–12 Jul
$3,020 SGD
$2,313 SGD
Show price breakdown
for 5 nights
Top guest favourite
Guest favourite
Home in Des Plains
Luxury 4 Bed 2.5 Bath near Chicago O'Hare Airport
4.88 out of 5 average rating, 144 reviews
4.88 (144)
,
·
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
2.5 bathrooms
2.5 bathrooms
9–14 Aug
9–14 Aug
$1,551 SGD
Show price breakdown
for 5 nights
$1,551 SGD for 5 nights
1
2
3
4
…
15