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
Apartment in Chicago
4.92 out of 5 average rating, 309 reviewsSpacious & private! Free parking! Great location!
Guest favourite
Apartment in Chicago
4.98 out of 5 average rating, 201 reviewsSpacious 2BR on Quiet St - Free Park/Late Checkout
Guest favourite
Guest suite in Chicago
4.98 out of 5 average rating, 114 reviewsGorgeous Studio 15 Minutes From Ohare!
Guest favourite
Guest suite in Chicago
4.95 out of 5 average rating, 191 reviewsAttic cozy guests suite near South Loop in Chicago
Superhost
Apartment in Chicago
4.84 out of 5 average rating, 132 reviewsPerfect Private Getaway in Perfect Pilsen
Guest favourite
Apartment in Chicago
4.96 out of 5 average rating, 101 reviewsCute, Clean, Cozy Apartment in Pilsen
Guest favourite
Guest suite in Chicago
4.92 out of 5 average rating, 85 reviewsCozy one-bedroom suite in the heart of West Loop
Guest favourite
Apartment in Chicago
5.0 out of 5 average rating, 23 reviewsCozy Garden Unit in Logan Square
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Accommodation & holiday rentals
- Lake Michigan Beach Accommodation & holiday rentals
- Saugatuck Accommodation & holiday rentals
- Evanston Accommodation & holiday rentals
- South Haven Holiday rentals
- Naperville Accommodation & holiday rentals
- South Side Accommodation & holiday rentals
- South Bend Accommodation & holiday rentals
- New Buffalo Holiday rentals
- Chicago Accommodation & holiday rentals
- Fitness-friendly rentals West Side
- Rentals with a home theatre West Side
- Rentals with an EV charger West Side
- Rentals with a sauna West Side
- Pet-friendly rentals West Side
- Smoking-friendly rentals West Side
- Rentals with a balcony West Side
- Rentals with lake access West Side
- Waterfront rentals West Side
- Rentals with breakfast West Side
- Rentals with beach access West Side
- Loft rentals West Side
- Condo rentals West Side
- Rentals with a washing machine and dryer West Side
- Monthly Rentals West Side
- Rentals with a fireplace West Side
- Private suite rentals West Side
- Rentals with a patio West Side
- Townhouse rentals West Side
- Apartment rentals West Side
- Rentals with a fire pit West Side
- Rentals with pools West Side
- Rentals with outdoor seating West Side
- Family-friendly rentals West Side
- Kid-friendly rentals West Side
- House rentals West Side
- Guesthouse rentals West Side
- Rentals with a hot tub West Side
- Hotel rentals West Side
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