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Search results; Over 1,000 homes in Westchester

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Guest favourite
Home in Westchester
Jacuzzi, King Beds, Easy Access to DT Chicago!
4 bedrooms, 4 beds, 2.5 private bathrooms
19–25 Oct
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4.96 out of 5 average rating, 136 reviews
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Guest favourite
Flat in Westchester
Westchester Corporate Stay 5 Beds
3 bedrooms, 7 beds
21–26 Sept
4.86 out of 5 average rating, 7 reviews
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Superhost
Flat in Westchester
Near Chicago - Sleeps 10 - Westchester
2 bedrooms, 6 beds
27 Sept – 2 Oct
New place to stay
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Guest favourite
Home in Westchester
Quiet Suburban Westchester Home
3 bedrooms, 3 beds
18–23 Oct
4.98 out of 5 average rating, 60 reviews
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Top guest favourite
Home in Brookfield
Homey Brookfield Gem — 4 Beds, 2 Baths, Great Yard
4 bedrooms, 4 beds
27 Sept – 2 Oct
4.95 out of 5 average rating, 21 reviews
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Superhost
Flat in Berwyn
The Woodland Escape
2 bedrooms, 2 queen beds
19–24 Sept
New place to stay
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Top guest favourite
Home in Berwyn
Chic Bungalow Near Chicago - Stained Glass Gem
4 bedrooms, 4 beds
30 Sept – 5 Oct
5.0 out of 5 average rating, 28 reviews
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Top guest favourite
Home in Brookfield
Cozy Home in Brookfield
2 bedrooms, 2 beds
18–23 Oct
4.99 out of 5 average rating, 107 reviews
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Guest favourite
Home in Berwyn
Beautiful 4 bedroom 3 full bath Bungalow
4 bedrooms, 4 beds
27 Sept – 2 Oct
4.94 out of 5 average rating, 138 reviews
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Superhost
Home in Bellwood
Near O'Hare huge home for all occasions
4 bedrooms, 6 beds
4–9 Oct
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Guest favourite
Apartment in Berwyn
Red Door
4 bedrooms, 4 queen beds
20–25 Sept
5.0 out of 5 average rating, 11 reviews
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Guest favourite
Home in Berwyn
Paradise in the Park
4 bedrooms, 4 beds
20–25 Sept
4.93 out of 5 average rating, 42 reviews
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Top guest favourite
Flat in Oak Park
Large sunny 3BR apt. in downtown Oak Park
3 bedrooms, 5 beds
25–30 Oct
4.92 out of 5 average rating, 209 reviews
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Top guest favourite
Flat in Oak Park
Spacious & Modern Treetop Oasis King Bed + Parking
2 bedrooms, 4 beds
1–6 Nov
4.98 out of 5 average rating, 99 reviews
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Top guest favourite
Guest suite in Oak Park
Entire upstairs in Arts and Crafts Oak Park home
2 bedrooms, 3 beds
12–17 Oct
4.91 out of 5 average rating, 542 reviews
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Top guest favourite
Flat in Oak Park
Comfortable & Easy
2 bedrooms, 3 queen beds
13–18 Oct
5.0 out of 5 average rating, 11 reviews
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Flat in Chicago
Luxury penthouse with city views
3 bedrooms, 4 beds
20–25 Sept
New place to stay
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Top guest favourite
Home in Chicago
Chicago Home (1st floor) by Midway near Downtown
3 bedrooms, 3 beds
24–29 Oct
4.95 out of 5 average rating, 110 reviews
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Top guest favourite
Home in Brookfield
Coffee Bar, Game Room, Walk to Train
4 bedrooms, 6 beds
12–17 Oct
4.97 out of 5 average rating, 38 reviews