Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Homes
Homes
Experiences
Experiences
Services
Services
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
Photo 1 of 29
Top guest favourite
Guest favourite
Apartment in Highland Park
Green oasis in law suite
1 bedroom
,
·
1 bed
,
·
1 private bathroom
8–13 Sept
8–13 Sept
$1,621 SGD
$1,430 SGD
Show price breakdown
for 5 nights
,
·
5.0 out of 5 average rating, 66 reviews
5.0 (66)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Highland Park
Cozy 2-Bedroom Cottage Near Downtown Highland Park
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
,
·
1 bathroom
1 bathroom
7–12 Sept
7–12 Sept
$1,964 SGD
$1,663 SGD
Show price breakdown
for 5 nights
4.94 out of 5 average rating, 186 reviews
4.94 (186)
Photo 1 of 26
Top guest favourite
Guest favourite
Home in Highland Park
North Shore - Home Away From Home
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
21–26 Sept
21–26 Sept
$2,997 SGD
Show price breakdown
for 5 nights
$2,997 SGD for 5 nights
5.0 out of 5 average rating, 44 reviews
5.0 (44)
Photo 1 of 19
Top guest favourite
Guest favourite
Cottage in Highland Park
Re-imagined 1880s cottage by Highwood, Metra, Lake
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
19–24 Sept
19–24 Sept
$2,374 SGD
Show price breakdown
for 5 nights
$2,374 SGD for 5 nights
4.98 out of 5 average rating, 114 reviews
4.98 (114)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Highland Park
5 min to Ravinia*Navy Base*Sleeps 7*Smart TVs
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
4 bathrooms
4 bathrooms
7–12 Sept
7–12 Sept
$3,189 SGD
$2,624 SGD
Show price breakdown
for 5 nights
4.95 out of 5 average rating, 21 reviews
4.95 (21)
Photo 1 of 11
Top guest favourite
Guest favourite
Guest suite in Highland Park
Charming space w/ use of deck and yard
1 bedroom
1 bedroom
,
·
2 queen beds
2 queen beds
,
·
1 bathroom
1 bathroom
28 Sept – 3 Oct
28 Sept – 3 Oct
$1,470 SGD
$1,289 SGD
Show price breakdown
for 5 nights
Free cancellation
4.97 out of 5 average rating, 166 reviews
4.97 (166)
Photo 1 of 27
Top guest favourite
Guest favourite
Home in Highland Park
North Shore Blue-Door Bungalow
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
15–20 Sept
15–20 Sept
$2,675 SGD
Show price breakdown
for 5 nights
$2,675 SGD for 5 nights
4.94 out of 5 average rating, 47 reviews
4.94 (47)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Highland Park
6 bed pool Indoor Basketball Gym
6 bedrooms
6 bedrooms
,
·
6 beds
6 beds
,
·
6.5 bathrooms
6.5 bathrooms
20–25 Nov
20–25 Nov
$12,885 SGD
Show price breakdown
for 5 nights
$12,885 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 11 reviews
5.0 (11)
Photo 1 of 29
Guest favourite
Guest favourite
Flat in Highwood
Cozy Highwood Apt 4 BR 2 train stops to Naval Base
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
1 bathroom
1 bathroom
7–12 Sept
7–12 Sept
$2,352 SGD
Show price breakdown
for 5 nights
$2,352 SGD for 5 nights
5.0 out of 5 average rating, 8 reviews
5.0 (8)
Photo 1 of 29
Top guest favourite
Guest favourite
Cottage in Highwood
The Pleasant Hill Cottage North Shore Enchantment
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
2.5 bathrooms
2.5 bathrooms
7–12 Sept
7–12 Sept
$6,826 SGD
Show price breakdown
for 5 nights
$6,826 SGD for 5 nights
5.0 out of 5 average rating, 17 reviews
5.0 (17)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Des Plains
Luxury 4 Bed 2.5 Bath near Chicago O'Hare Airport
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
2.5 bathrooms
2.5 bathrooms
25–30 Oct
25–30 Oct
$1,326 SGD
Show price breakdown
for 5 nights
$1,326 SGD for 5 nights
4.88 out of 5 average rating, 153 reviews
4.88 (153)
Photo 1 of 29
Top guest favourite
Guest favourite
Guest suite in Riverwoods
Master qtr close to nature & easy urban facilities
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
24–29 Oct
24–29 Oct
$909 SGD
Show price breakdown
for 5 nights
$909 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 506 reviews
4.95 (506)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Northbrook
6 Kings | Ping-Pong | Gazebo!
5 bedrooms
5 bedrooms
,
·
6 king beds
6 king beds
,
·
3.5 bathrooms
3.5 bathrooms
27 Sept – 2 Oct
27 Sept – 2 Oct
$3,299 SGD
$2,975 SGD
Show price breakdown
for 5 nights
4.9 out of 5 average rating, 52 reviews
4.9 (52)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Glenview
Charming Entire House
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
8–13 Nov
8–13 Nov
$1,596 SGD
Show price breakdown
for 5 nights
$1,596 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 85 reviews
4.98 (85)
Photo 1 of 22
Top guest favourite
Guest favourite
Flat in Evanston
Stylish & Comfy Gem near Downtown~Balcony~Parking
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
20–25 Sept
20–25 Sept
$1,354 SGD
$1,163 SGD
Show price breakdown
for 5 nights
Free cancellation
4.96 out of 5 average rating, 318 reviews
4.96 (318)
Photo 1 of 27
Hotel room in Bannockburn
Exec King Suite | La Quinta Deerfield | Pool Day
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
6–11 Sept
6–11 Sept
$862 SGD
Show price breakdown
for 5 nights
$862 SGD for 5 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Northbrook
*King bed *Outdoor Living *Sought-After Area
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1.5 bathrooms
1.5 bathrooms
13–18 Oct
13–18 Oct
$3,048 SGD
Show price breakdown
for 5 nights
$3,048 SGD for 5 nights
4.98 out of 5 average rating, 132 reviews
4.98 (132)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Northbrook
1 Mi to Metra: Estate w/ Theater, Game Room & More
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
7 bathrooms
7 bathrooms
7–12 Sept
7–12 Sept
$7,958 SGD
Show price breakdown
for 5 nights
$7,958 SGD for 5 nights
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Photo 1 of 29
Top guest favourite
Guest favourite
Flat in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
29 Nov – 4 Dec
29 Nov – 4 Dec
$795 SGD
Show price breakdown
for 5 nights
$795 SGD for 5 nights
Free cancellation
4.99 out of 5 average rating, 110 reviews
4.99 (110)
1
2
3
4
…
15