filters

Search results; Over 1,000 homes in Highland Park

Photo 1 of 29
Guest favourite
Home in Highland Park
2-Acre Highland Park Retreat with Heated Pool ~ 5*
6 bedrooms, 6 beds, 4 private bathrooms
4–9 Oct
,
4.91 out of 5 average rating, 154 reviews
Photo 1 of 19
Top guest favourite
Cottage in Highland Park
Re-imagined 1880s cottage by Highwood, Metra, Lake
2 bedrooms, 4 beds, 1 bathroom
11–16 Oct
4.98 out of 5 average rating, 115 reviews
Photo 1 of 29
Guest favourite
Home in Highland Park
Cozy 2-Bedroom Cottage Near Downtown Highland Park
2 bedrooms, 2 queen beds, 1 bathroom
1–6 Oct
4.93 out of 5 average rating, 192 reviews
Photo 1 of 26
Top guest favourite
Home in Highland Park
North Shore - Home Away From Home
4 bedrooms, 5 beds, 2 bathrooms
13–18 Oct
4.98 out of 5 average rating, 46 reviews
Photo 1 of 29
Guest favourite
Flat in Highland Park
Lovely studio near the beach! (and heated floors!)
1 bedroom, 1 queen bed, 1 bathroom
25–30 Oct
4.92 out of 5 average rating, 209 reviews
Photo 1 of 29
Top guest favourite
Home in Highland Park
6 bed pool Indoor Basketball Gym
6 bedrooms, 6 beds, 6.5 bathrooms
28 Dec – 4 Jan
5.0 out of 5 average rating, 11 reviews
Photo 1 of 27
Top guest favourite
Home in Highland Park
North Shore Blue-Door Bungalow
3 bedrooms, 4 beds, 1 bathroom
3–8 Oct
4.94 out of 5 average rating, 47 reviews
Photo 1 of 29
Top guest favourite
Home in Highland Park
5 min to Ravinia*Navy Base*Sleeps 7*Smart TVs
3 bedrooms, 4 beds, 4 bathrooms
8–13 Oct
4.96 out of 5 average rating, 23 reviews
Photo 1 of 11
Top guest favourite
Guest suite in Highland Park
Charming space w/ use of deck and yard
1 bedroom, 2 queen beds, 1 bathroom
1–6 Oct
4.97 out of 5 average rating, 167 reviews
Photo 1 of 29
Top guest favourite
Cottage in Highwood
The Pleasant Hill Cottage North Shore Enchantment
3 bedrooms, 6 beds, 2.5 bathrooms
11–16 Oct
5.0 out of 5 average rating, 18 reviews
Photo 1 of 29
Guest favourite
Flat in Highwood
Cozy Highwood Apt 4 BR 2 train stops to Naval Base
4 bedrooms, 5 beds, 1 bathroom
5–10 Oct
5.0 out of 5 average rating, 10 reviews
Photo 1 of 29
Top guest favourite
Guest suite in Riverwoods
Master qtr close to nature & easy urban facilities
1 bedroom, 2 beds, 1 bathroom
29 Oct – 3 Nov
4.95 out of 5 average rating, 510 reviews
Photo 1 of 27
Hotel room in Bannockburn
Exec King Suite | La Quinta Deerfield | Pool Day
1 bedroom, 2 beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 4 reviews
Photo 1 of 29
Top guest favourite
Home in Northbrook
*King bed *Outdoor Living *Sought-After Area
3 bedrooms, 3 beds, 1.5 bathrooms
1–6 Oct
4.98 out of 5 average rating, 134 reviews
Photo 1 of 19
Home in Highland Park
Fresh and stylish family home near Lake Michigan
3 bedrooms, 5 beds, 2.5 bathrooms
1–6 Oct
4.86 out of 5 average rating, 7 reviews
Photo 1 of 29
Guest favourite
Home in Northbrook
1 Mi to Metra: Estate w/ Theater, Game Room & More
4 bedrooms, 4 beds, 7 bathrooms
1–6 Oct
5.0 out of 5 average rating, 5 reviews
Photo 1 of 10
Top guest favourite
Home in Lake Bluff
Home Sweet Home, minutes to Great Lakes Naval Base
3 bedrooms, 4 beds, 1 bathroom
3–8 Oct
4.95 out of 5 average rating, 197 reviews
Photo 1 of 27
Top guest favourite
Home in Lake Forest
Spacious Home-Great Lakes Close-Quiet Location
5 bedrooms, 5 beds, 4 bathrooms
9–14 Nov
5.0 out of 5 average rating, 37 reviews
Photo 1 of 14
Featured hotel
Hotel in Rosemount
Sonesta Chicago O'Hare Airport Rosemont, Accessib.
1 bedroom, 1 king bed, 1 bathroom
11–16 Oct
5.0 out of 5 average rating, 3 reviews