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Search results; Over 1,000 homes in Westchester

Guest favourite
Home in Westchester
Modern 2Bdrm Westchester/Chicago Home.With Hot tub
2 bedrooms, 3 beds, 1 private bathroom
4–9 Oct
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4.87 out of 5 average rating, 103 reviews
Superhost
Flat in Westchester
Near Chicago - Sleeps 10 - Westchester
2 bedrooms, 6 beds, 1 bathroom
27 Sept – 2 Oct
New place to stay
Guest favourite
Home in Westchester
Quiet Suburban Westchester Home
3 bedrooms, 3 beds, 2 bathrooms
18–23 Oct
4.98 out of 5 average rating, 60 reviews
Top guest favourite
Home in Brookfield
Homey Brookfield Gem — 4 Beds, 2 Baths, Great Yard
4 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
4.95 out of 5 average rating, 21 reviews
Top guest favourite
Home in Berwyn
Chic Bungalow Near Chicago - Stained Glass Gem
4 bedrooms, 4 beds, 2 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 28 reviews
Flat in Chicago
Luxury penthouse with city views
3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
New place to stay
Top guest favourite
Home in Brookfield
Coffee Bar •Game Room •Walk to Train •Garage
4 bedrooms, 6 beds, 3 bathrooms
12–17 Oct
4.97 out of 5 average rating, 37 reviews
Superhost
Home in Bellwood
Near O'Hare huge home for all occasions
4 bedrooms, 6 beds, 3.5 bathrooms
28 Sept – 3 Oct
Top guest favourite
Home in Brookfield
Cozy Home in Brookfield
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
4.99 out of 5 average rating, 107 reviews
Guest favourite
Home in Villa Park
Cozy 5BD Home with Scandinavian Vibes
5 bedrooms, 5 beds, 2 bathrooms
27 Sept – 2 Oct
4.91 out of 5 average rating, 44 reviews
Guest favourite
Apartment in Berwyn
Red Door
4 bedrooms, 4 queen beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Addison
Private & quiet🌲 O'Hare 8mi✈️ D/T Chicago 22mi 🏙
3 bedrooms, 5 beds, 2 bathrooms
29 Sept – 4 Oct
4.99 out of 5 average rating, 93 reviews
Guest favourite
Flat in Oak Park
Top floor of Historic Oak Park Home /2 Car Garage
3 bedrooms, 5 beds, 1 bathroom
21–26 Sept
4.96 out of 5 average rating, 127 reviews
Guest favourite
Home in Itasca
At the center of it all, a secret suburban gem!
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.71 out of 5 average rating, 34 reviews
Top guest favourite
Home in Bensenville
Grand 6BR, 4.5BA Game Rm Near O’Hare, & Down Town
5 bedrooms, 8 beds, 4.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Home in Maywood
Charming 4BR | 2 living rooms & game area
4 bedrooms, 5 queen beds, 2 bathrooms
14–19 Dec
4.95 out of 5 average rating, 20 reviews
Top guest favourite
Flat in Oak Park
Large sunny 3BR apt. in downtown Oak Park
3 bedrooms, 5 beds, 1 bathroom
25–30 Oct
4.92 out of 5 average rating, 209 reviews
Guest favourite
Home in Lombard
Grand Retreat/5Brs/Game Room
5 bedrooms, 6 beds, 2 bathrooms
12–17 Oct
5.0 out of 5 average rating, 50 reviews
Guest favourite
Home in Des Plains
Rosemont 4BD2BA house with Pool
4 bedrooms, 5 beds, 2 bathrooms
19–24 Sept
5.0 out of 5 average rating, 27 reviews