
Holiday houses in West Side
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in West Side
Guests agree: these stays are highly rated for location, cleanliness and more.
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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, 33 reviewsFamily Friendly Duplex/9 min from MDW/Free Parking
NoelleRating, 5 stars3 days ago
Loved our stay in Chicago! Johanna was a WONDERFUL host!! Very helpful and very clear instructions for check in and out. When I needed to get ahold of her it was super easy to connect with her. House is adorable and very home like feeling :) would definitely recommend staying here!
Superhost

Home in Schaumburg
4.8 out of 5 average rating, 80 reviewsSpacious 5 Bedroom 1 Level Renovated Modern House
NolanRating, 5 stars3 weeks ago
Great place to stay. I would recommend to everyone.
Guest favourite

Apartment in Chicago
4.95 out of 5 average rating, 39 reviewsElegant 4Bedroom with Free Parking in Albany Park
MatthewRating, 5 stars3 weeks ago
Thank you for letting us stay in your beautiful home. Everything was exactly as described! Will definitely stay again
Superhost

Apartment in Chicago
4.81 out of 5 average rating, 16 reviewsCity Gem: Stylish 3BR for Urban Explorers
MaríaRating, 5 stars2 months ago
Excellent lodging and host, I would come back!
Guest favourite

Home in Lockport
5 out of 5 average rating, 19 reviewsCozy 4 Bed Ranch w Fenced Yard *Netflix
StephanieRating, 5 stars1 week ago
Samantha’s home was a great landing spot in an easy location for us to visit with nearby family. Five adults and one toddler were very comfortable and enjoyed the space. The house is well appointed with everything we needed, and we appreciated the extra toys and high chair. The neighborhood is quiet and peaceful, while being near amenities and major highways. The listing description, Samantha’s instructions, and the posted instructions in the house made for a seamless stay.
Superhost

Condo in Chicago
4.79 out of 5 average rating, 29 reviewsSpacious condo with open floor plan and fireplace
TatianaRating, 5 stars1 month ago
This place was spacious and perfect for our family (two kids and a baby), with plenty of room for everyone to spread out. The hosts were fantastic! They encountered an issue with the fridge not working just before our arrival but handled it professionally, providing excellent support until it was fixed. We really appreciated their responsiveness and care. We highly recommend this space for families and large groups. One small suggestion: if you’re a light sleeper or have kids, consider bringing a noise machine, as some sound from the upstairs neighbors can be heard. However, this wasn’t a problem for us and is to be expected when staying in a condo.
Guest favourite

Home in Lombard
5 out of 5 average rating, 21 reviewsSpacious Home in Chicago Suburbs
JonathanRating, 5 stars2 weeks ago
Fantastic spot. Came for a local event with some friends and definitely was not disappointed. Made my first ever Airbnb experience super easy and low stress.
Guest favourite

Home in Gary
4.96 out of 5 average rating, 69 reviewsPrivate 5 Star 2 bedroom modern city farmhouse
AmberRating, 5 stars2 months ago
Angela was very responsive. That house is right off the highway so it’s easy to get to the sheets and linens. Everything was very clean. House was set up so cute. Made us feel right at home. The neighborhood was very quiet also. Would recommend 100% and hope to stay there again when I’m in town! 5 star!
Destinations to explore
- Downtown Chicago Holiday rentals
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- 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
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- Rentals with an EV charger West Side
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- Townhouse rentals West Side
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- Loft rentals West Side
- Rentals with a washing machine and dryer West Side
- Fitness-friendly rentals West Side
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