
Holiday houses in West Side
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Top-rated holiday rentals in West Side
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
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Popular amenities for West Side holiday rentals
Other great holiday rentals in West Side
Guest favourite

Home in Chicago
4.94 out of 5 average rating, 32 reviewsFamily Friendly Duplex/9 min from MDW/Free Parking
Superhost

Home in Schaumburg
4.8 out of 5 average rating, 79 reviewsSpacious 5 Bedroom 1 Level Renovated Modern House
Guest favourite

Apartment in Chicago
4.95 out of 5 average rating, 39 reviewsElegant 4Bedroom with Free Parking in Albany Park
Superhost

Apartment in Chicago
4.81 out of 5 average rating, 16 reviewsCity Gem: Stylish 3BR for Urban Explorers
Guest favourite

Home in Lockport
5 out of 5 average rating, 19 reviewsCozy 4 Bed Ranch w Fenced Yard *Netflix
Superhost

Condo in Chicago
4.79 out of 5 average rating, 29 reviewsSpacious condo with open floor plan and fireplace
Guest favourite

Home in Lombard
5 out of 5 average rating, 21 reviewsSpacious Home in Chicago Suburbs
Guest favourite

Home in Gary
4.96 out of 5 average rating, 69 reviewsPrivate 5 Star 2 bedroom modern city farmhouse
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- North Side Holiday rentals
- South Bend Holiday rentals
- Lake Michigan Beach Holiday rentals
- South Side Holiday rentals
- Evanston Holiday rentals
- South Haven Holiday rentals
- Saugatuck Holiday rentals
- Naperville Holiday rentals
- Chicago Holiday rentals
- Rentals with a fireplace West Side
- Rentals with beach access West Side
- Rentals with an EV charger West Side
- Rentals with a sauna West Side
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- House rentals West Side
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- Townhouse rentals West Side
- Rentals with a balcony West Side
- Rentals with a home theatre West Side
- Rentals with lake access West Side
- Condo rentals West Side
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- Rentals with a fire pit West Side
- Family-friendly rentals West Side
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- Monthly Rentals West Side
- Rentals with pools West Side
- Rentals with a patio West Side
- Private suite rentals West Side
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- Hotel rentals West Side
- Pet-friendly rentals West Side
- Smoking-friendly rentals West Side
- Kid-friendly rentals West Side
- Rentals with a hot tub West Side
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