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Search results; 285 places in Winnetka

Guest favorite
Home in Highland Park
2-Acre Highland Park Retreat with Heated Pool ~ 5*
6 beds
Apr 1 – 6
4.9 out of 5 average rating, 124 reviews
Guest favorite
Condo in Evanston
"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
4 beds
May 13 – 18
4.96 out of 5 average rating, 75 reviews
Guest favorite
Condo in Evanston
"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool
5 beds
Apr 7 – 12
4.97 out of 5 average rating, 69 reviews
Superhost
Apartment in Evanston
Spirit of Evanston Oversize 1BDR
3 beds
Apr 19 – 24
5.0 out of 5 average rating, 6 reviews
Superhost
Home in Schaumburg
Paradise 4BR w/ Pool & Games
5 beds
Apr 1 – 6
New place to stay
Superhost
Home in Evanston
Beautiful Historic Colonial
7 beds
Apr 4 – 9
4.87 out of 5 average rating, 39 reviews
Apartment in Rosemont
Relaxing Standard Room l Free Airport Shuttle
1 king bed
Apr 1 – 6
New place to stay
Apartment in Schiller Park
Iconic City | Botanic Garden. Free Shuttle
1 king bed
Apr 1 – 6
4.15 out of 5 average rating, 13 reviews
Superhost
Home in Highland Park
6 bed pool Indoor Basketball Gym
6 beds
Aug 8 – 13
Guest favorite
Home in Schaumburg
Schaumburg Woodfield Pool House 4bedroom 2.5bath
5 beds
May 1 – 6
4.93 out of 5 average rating, 14 reviews
Guest favorite
Home in Niles
Luxury Modern House Epic Master Bath & Pool Table
5 beds
Apr 1 – 6
5.0 out of 5 average rating, 12 reviews
Superhost
Home in Lake Forest
Beautiful 137 Year Old Farm Home (3night min)
6 beds
Aug 19 – 24
4.91 out of 5 average rating, 58 reviews
Guest favorite
Home in Glen Ellyn
4K SqFt Home w/ Heated Pool & Hot Tub (Open Apr 8)
7 beds
Apr 1 – 7
4.97 out of 5 average rating, 31 reviews
Guest favorite
Home in Grayslake
Family-sized Indoor Heated Pool & Movie Theater!
11 beds
Apr 8 – 13
5.0 out of 5 average rating, 12 reviews
Guest favorite
Condo in Lisle
Peaceful Condo in Lisle, Illinois
1 king bed
Apr 26 – May 1
4.95 out of 5 average rating, 38 reviews
Superhost
Room in Deerfield
Stay with AnastasiaHealthcare,
Private Bedroom near Metra, 20 min to Airport
Apr 5 – 10
4.77 out of 5 average rating, 132 reviews
Apartment in Morton Grove
Corporate Housing by MGM
2 queen beds
Apr 6 – 11
4.77 out of 5 average rating, 35 reviews
Guest favorite
Guest suite in Bartlett
Cozy & Spacious Suite in Quiet Neighborhood
2 beds
May 12 – 17
4.97 out of 5 average rating, 183 reviews