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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, 2 bathrooms
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, 1 bathroom
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, 2 bathrooms
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, 2 bathrooms
27 Sept – 2 Oct
4.95 out of 5 average rating, 21 reviews
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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
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Top guest favourite
Home in Brookfield
Cozy Home in Brookfield
2 bedrooms, 2 beds, 1 bathroom
18–23 Oct
4.99 out of 5 average rating, 107 reviews
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Guest favourite
Apartment in Berwyn
Red Door
4 bedrooms, 4 queen beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 11 reviews
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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
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Guest favourite
Home in Berwyn
Beautiful 4 bedroom 3 full bath Bungalow
4 bedrooms, 4 beds, 3 bathrooms
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, 3.5 bathrooms
4–9 Oct
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Guest favourite
Home in La Grange
Elegant Escape in Top Location
5 bedrooms, 6 beds, 2.5 bathrooms
20–25 Sept
4.83 out of 5 average rating, 24 reviews
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Top guest favourite
Flat in Oak Park
Spacious & Modern Treetop Oasis King Bed + Parking
2 bedrooms, 4 beds, 1 bathroom
1–6 Nov
4.98 out of 5 average rating, 99 reviews
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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
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Home in Forest Park
Ferdinand Rear Home
2 bedrooms, 2 queen beds, 1 bathroom
26–31 Dec
New place to stay
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Flat in Chicago
Luxury penthouse with city views
3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
New place to stay
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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, 1 bathroom
2–7 Oct
4.91 out of 5 average rating, 542 reviews
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Top guest favourite
Home in Chicago
Chicago Home (1st floor) by Midway near Downtown
3 bedrooms, 3 beds, 1 bathroom
24–29 Oct
4.95 out of 5 average rating, 110 reviews
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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