Holiday rentals 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
Get the amount of space that is right for you
Popular amenities for West Side holiday rentals
Other great holiday rentals in West Side
Guest favourite
Flat in Chicago
4.87 out of 5 average rating, 190 reviews2 bedroom apartment near train line and bus lines!
Guest favourite
Flat in Chicago
4.96 out of 5 average rating, 167 reviews2BR Centrally Located in Cozy Hip Logan Square
Superhost
Flat in Berwyn
5.0 out of 5 average rating, 10 reviewsFriendly Songbird Suite
Guest favourite
Flat in Chicago
5.0 out of 5 average rating, 17 reviewsFlor de Luna ~ Little Village Chicago Retreat
Guest favourite
Guest suite in Berwyn
4.94 out of 5 average rating, 49 reviewsBest Place to Rest, near Chicago
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
Flat in Forest Park
4.91 out of 5 average rating, 22 reviewsCity-Accessible Basement Retreat
Superhost
Home in Chicago
4.89 out of 5 average rating, 36 reviewsBrand New Spacious Duplex
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- South Bend Holiday rentals
- New Buffalo Holiday rentals
- Chicago Holiday rentals
- Rentals with a fireplace West Side
- Rentals with a balcony West Side
- Monthly Rentals West Side
- Rentals with a hot tub West Side
- Rentals with a patio West Side
- Rentals with pools West Side
- Pet-friendly rentals West Side
- Smoking-friendly rentals West Side
- Flat rentals West Side
- Rentals with a firepit West Side
- Rentals with a cinema West Side
- Guest house rentals West Side
- Rentals with a washing machine and dryer West Side
- Hotel rentals West Side
- Waterfront rentals West Side
- Family-friendly rentals West Side
- House rentals West Side
- Rentals with lake access West Side
- Apartment rentals West Side
- Family-friendly rentals West Side
- Private suite rentals West Side
- Rentals with outdoor seating West Side
- Loft rentals West Side
- Rentals with beach access West Side
- Townhouse rentals West Side
- Rentals with an EV charger West Side
- Rentals with a sauna West Side
- Fitness-friendly rentals West Side
- Rentals with breakfast West Side
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