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House holiday rentals in West Side

Find and book unique houses on Airbnb

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Popular amenities for house rentals in West Side

House rentals with a pool

Guest favourite
Home in Munster
5 out of 5 average rating, 11 reviews

Munster hide away

ChristopherRating, 5 stars5 months ago
Nice house with updates. We used all four bedrooms, so everyone had their own space. Kitchen and living room looked nice, but a bit cozy if everyone was in the space at the same time. There was a large breakfast nook/counter in the kitchen instead of a table. More dishes, mugs, etc. in the kitchen would have been nice. The coffee maker and provided K-cups were great! Would definitely stay again if it's available when we are in the area again.
Superhost
Home in Des Plaines
5 out of 5 average rating, 4 reviews

Rosemont 4BD2BA house with Pool

HannahRating, 5 stars1 month ago
Mike was very responsive leading up to our stay and very helpful whenever I had any questions about the property. The home was very clean and well maintained. Would recommend!
Guest favourite
Home in Bloomingdale
4.92 out of 5 average rating, 52 reviews

Now Open: Heated Pool with Entire House

AmyRating, 5 stars1 day ago
Really great place to stay, super responsive host! The pool was pretty great and so was the hot tub! Great location too, lots of stores, restaurants around, and parks like the Busse Woods (it’s huge and lots of walking paths)!
Guest favourite
Home in Schaumburg
4.93 out of 5 average rating, 27 reviews

Schaumburg Oasis:Private Pool & Enchanted Garden

TeddyRating, 5 stars1 week ago
They were a fantastic host, very responsive to every question and anything we needed. The location is quiet and amazing, great place to relax and enjoy time. love the pool! Will definitely stay again. 100% recommend!
Superhost
Home in Chicago
4.88 out of 5 average rating, 56 reviews

Luxury Loft with Private Pool and Movie Theater

RyanRating, 5 stars1 week ago
Damani was a great host, really responsive and easy to communicate with! The house was exactly as advertised and really nice! The pool was great!
Superhost
Home in Skokie
New place to stay

Luxury fenced in modern ranch

PatriciaRating, 5 stars1 week ago
It was a chaotic start to our vacation stemming off my daughter's graduation from Northwestern; however, Jennifer immediately took the stress off my shoulders and welcomed our family to a fabulous stay at her home. Words cannot express how grateful my family is and without Jennifer's help it would not have been as successfull. I highly recommend staying at any of her properties. She will go above and beyond to make sure you're stay is wonderful!
Home in Chicago
New place to stay

LUXE - Movie Theater + Spa House

JuanRating, 5 stars2 weeks ago
Great getaway place to stay at. Beautiful patio area as well!
Guest favourite
Home in Carol Stream
4.86 out of 5 average rating, 7 reviews

Spacious 4 Bed/3.5 Bath Sleeps 8+

CarmenRating, 5 stars8 months ago
Beautiful house very clean and comfortable. We'll be back very soon

Weekly house rentals

Superhost
Home in Chicago
4.8 out of 5 average rating, 84 reviews

Entire 2 BR home w/ office, deck & no clean fee!

JamelaRating, 5 stars3 months ago
Great host. Very responsive and clear with instructions. Highly recommended
Superhost
Home in Chicago
4.72 out of 5 average rating, 54 reviews

Animal House near Sox stadium

ChristineRating, 5 stars1 month ago
If you're traveling with a pet I would highly recommend this place! Great location and great communication throughout our stay.
Guest favourite
Home in Chicago
4.93 out of 5 average rating, 44 reviews

Floresitas Oasis, your home in Chicago

Kawina RochelleRating, 5 stars3 days ago
Lizbeth was an amazing host. She’s responsive and attentive. The place was exceptional clean and had an amazing smell. I was there to celebrate my birthday and was pleasantly surprised upon entry when I was greeted with a personalized birthday message, fresh flowers and a bottle of wine. Anytime I reached out to Lizbeth, she responded expeditiously. Again, very attentive. My husband and I will definitely stay at her beautiful Oasis again. We felt comfortable and completely safe. Everything we wanted to do was a quick drive from the location. If you’re considering staying at her home, you will not regret it. If I could give more than 5 stars, I would. Thanks Lizbeth for being an incredible host Until the next time…
Top guest favourite
Home in Chicago
5 out of 5 average rating, 26 reviews

Sunny Historic Cottage on the Park

MichelleRating, 5 stars6 months ago
We loved Megan’s place! It’s adorably decorated and very cozy. We felt at home during our stay. The beds were comfortable and the kitchen was great for cooking dinner one night. Checking in and out was really simple. You’re not immediately by the train, but it’s a quiet safe neighborhood and there’s a little park across the street and a cute coffee shop a short walk from the house. As was clearly indicated by the hosts, it’s notably warmer upstairs than it is downstairs (we stayed in November) but it wasn’t a real issue. Would happily stay here again.
Superhost
Home in Cicero
4.79 out of 5 average rating, 193 reviews

Spacious whole apt near shopping and city

CassieRating, 5 stars2 weeks ago
Host was very nice and helpful with our questions, nice neighborhood some noise but nothing too extreme & house was clean.
Top guest favourite
Home in Oak Park
4.94 out of 5 average rating, 34 reviews

Vintage Urban Retreat | Oak Park

BrianRating, 5 stars1 week ago
We had a great time at Gabriela's place. The listing was accurate, the location was great, and we were pleasantly surprised by how new and clean everything felt. Would stay again.
Superhost
Home in Chicago
5 out of 5 average rating, 4 reviews

Luxury-Near Downtown & United Center-Sleeps 14

AlexisRating, 5 stars1 week ago
Dan is a gracious host! He takes great pride in his property and making sure guests are comfortable and satisfied with their stay. I recommend this property to anyone who truly wants a home away from home stay! My family and I will book again next year!
Guest favourite
Home in Chicago
4.95 out of 5 average rating, 37 reviews

Mid-Century Gem By United Center: Hot Tub & Sauna

MatthewRating, 5 stars1 week ago
Had a great time at Sebastian’s place! The house was better than expected. Highly recommend staying here if you’re visiting Chicago.

Private house rentals

Guest favourite
Home in Chicago
5 out of 5 average rating, 10 reviews

The Modern Muse of Chicago! Close to everything!

VictoriaRating, 5 stars1 week ago
Jasna was an amazing host! The house was absolutely spectacular—truly even better than the photos. Every room felt thoughtfully designed and full of warmth, making it feel just like home. We had all the amenities we needed, which made our stay super comfortable and stress-free. It was the perfect setting for a special girls’ trip with my mom and sister. The neighborhood was peaceful and beautiful, adding to the relaxing vibe. We’ll definitely be back! Thank you again for everything, Jasna!
Superhost
Home in Chicago
4.92 out of 5 average rating, 48 reviews

Family Friendly Duplex/9 min from MDW/Free Parking

EhjayRating, 5 stars2 weeks ago
Very nice space to bring friends over
Top guest favourite
Home in Chicago
4.95 out of 5 average rating, 61 reviews

Chicago Home (1st floor) by Midway near Downtown

DelaneyRating, 5 stars6 days ago
My friends and I had a great time staying at Joanna’s place! It was super clean, the neighborhood was nice, and there were lots of stores and restaurants around the area too! We would definitely stay again :)
Guest favourite
Home in Oak Park
4.93 out of 5 average rating, 15 reviews

Spacious Designer Oasis: Game Room - Yard - Garage

Danielle GRating, 5 stars4 days ago
Rameez was an amazing host! Making the experience even more enjoyable with his quick responses & fast accommodations. The home is more spacious than it looks in the photos and it truly exceeded my expectations. I had a great stay for my birthday!
Top guest favourite
Home in Chicago
4.97 out of 5 average rating, 32 reviews

Cheerful two bedroom home with patio/deck

EricRating, 5 stars3 months ago
Beautiful home in a quiet neighborhood with responsive and helpful hosts.
Top guest favourite
Home in Chicago
4.9 out of 5 average rating, 367 reviews

Private 3rd Floor Apartment

RickRating, 5 stars1 month ago
Very comfy apartment in a great neighborhood. We were in town for a baseball game and it’s a terrific place for that, just about a 20-minute walk to Wrigley Field. The only thing to be concerned about is the stairs: there are two flights to get into the apartment and they’re fairly steep and small, so if you have mobility issues that would be a concern. I don’t and had no problem. Karen is a lovely host and was very helpful when I was getting into the place and unloading my stuff from my car. There are tons of restaurants and coffee shops in the area, so it’s a great place to explore and hang out.
Superhost
Home in Chicago
4.86 out of 5 average rating, 7 reviews

Perfect Location Across from Park & Train Station

CarlaRating, 5 stars4 weeks ago
The house was beautiful and was perfect for our group. Everything was spotlessly clean and just as described. Access to the El was convenient but also created quite a lot of noise especially in the front of the house. This, of course, is completely out of the host’s control and we got used to it after 24 hours or so. The location was also convenient to the interstate that flows right into downtown, which was great for us as we were participating in a conference in a hotel on Michigan Avenue. Overall we had a great experience with the house and the host. Would recommend this location very highly.
Guest favourite
Home in Chicago
4.96 out of 5 average rating, 23 reviews

Big house in the BEST Location!

JodiRating, 5 stars3 days ago
The house is lovely! Better than the pictures, just as all of the reviews say. The showers are incredible. The master bathroom is a dream. We had everything we needed & more. We don’t have a single complaint. We definitely plan on booking here again.

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