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
Guest suite in Chicago
4.9 out of 5 average rating, 104 reviewsNew Bright & Airy Entire Unit in Logan
Guest favourite
Loft in Chicago
4.9 out of 5 average rating, 224 reviewsEntire place with free parking.
Guest favourite
Apartment in Chicago
4.89 out of 5 average rating, 351 reviewsSunny Logan Square Artists' home
Guest favourite
Apartment in Chicago
4.96 out of 5 average rating, 103 reviewsCute, Clean, Cozy Apartment in Pilsen
Superhost
Apartment in Chicago
4.84 out of 5 average rating, 178 reviewsLa Cottage
Superhost
Guesthouse in Bridgeport
4.92 out of 5 average rating, 326 reviewsPrivate Studio in Bridgeport, Chicago
Superhost
Condo in Chicago
4.87 out of 5 average rating, 130 reviews3D Tour! Designer Condo near Logan Square
Guest favourite
Apartment in Oak Park
4.87 out of 5 average rating, 253 reviewsCosmopolitan Nest in Oak Park North Side
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 an EV charger West Side
- Rentals with a sauna West Side
- Waterfront rentals West Side
- Private suite rentals West Side
- Rentals with breakfast West Side
- Loft rentals West Side
- Rentals with a balcony West Side
- Rentals with lake access West Side
- Rentals with pools West Side
- Rentals with a home theatre West Side
- Apartment rentals West Side
- Rentals with a fire pit West Side
- Family-friendly rentals West Side
- Rentals with beach access West Side
- Rentals with a hot tub West Side
- Rentals with a washing machine and dryer West Side
- Monthly Rentals West Side
- Rentals with a fireplace West Side
- Kid-friendly rentals West Side
- Rentals with outdoor seating West Side
- Fitness-friendly rentals West Side
- Rentals with a patio West Side
- House rentals West Side
- Hotel rentals West Side
- Condo rentals West Side
- Townhouse rentals West Side
- Pet-friendly rentals West Side
- Smoking-friendly rentals West Side
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