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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

Home in Glen Ellyn
4.83 out of 5 average rating, 12 reviews

Pardizes Suites

CrystalRating, 5 stars1 week ago
I was speechless when I walked in her house it was beyond beautiful nothing was out of place at all when I say she had everything you can think of to accommodate us all she had all the toiletries you could think of the kitchen was stocked with all kind of seasonings dishes she even stocked breakfast sausages she put balloons out she really out done herself she went above and beyond it was plenty of games there the rooms were beautiful the beds were so comfortable I didn’t want to get up it was the best airbnb I ever stayed in we were all blown away by how beautiful and clean and neat it was Lisa is a very great hostess you all make sure to book with her she is great
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, 51 reviews

Now Open: Heated Pool with Entire House

TaraRating, 5 stars1 month ago
Moizs was an amazing host. Very accommodating, quick response, had some great recommendations for local restaurants, shopping, etc. Bloomingdale is a cute and nice suburb of Chicago. We had a great trip and we will definitely be back.
Guest favourite
Home in Schaumburg
4.93 out of 5 average rating, 27 reviews

Schaumburg Oasis:Private Pool & Enchanted Garden

TeddyRating, 5 stars4 days 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 Skokie
New place to stay

Luxury fenced in modern ranch

PatriciaRating, 5 stars3 days 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

LUXURY - Movie Theater + Spa House

JuanRating, 5 stars1 week 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

Guest favourite
Home in Chicago
4.96 out of 5 average rating, 91 reviews

City Cottage in Logan Square-Avondale

AshleyRating, 5 stars1 month ago
We loved this cute little house! Super walkable and close to lots of stuff in Logan Square; although we thoroughly enjoyed the peacefulness of hanging out in the private backyard. Would definitely stay again!
Guest favourite
Home in Chicago
4.96 out of 5 average rating, 74 reviews

NEW! 3BR/2.5B Duplex in Noble Sq

AdamRating, 5 stars1 month ago
Host is very accommodating and responsive. The place is nice and was in a great location. Only a short 10 minute drive that was a straight shot to Michigan Ave. The only thing we felt was slightly misleading was that we were under the impression that the 3rd bedroom with a couch was able to pull out and convert into a bed. Unfortunately, that wasn’t the case, so we ended up leveraging an air mattress we had packed as a contingency. Overall, we had an enjoyable stay and would recommend.
Guest favourite
Home in Chicago
5 out of 5 average rating, 14 reviews

Spacious | 3 Beds | Free St. Parking

JenniferRating, 5 stars2 weeks ago
Glomery was a great host. Our first trip to Chicago, so we weren’t too sure about the safety of the neighborhood, but overall a very nice experience and had all the necessities. Very clean and tidy. Beds were so comfortable with fluffy pillows. Plenty of towels, coffee and extra pillows. Easy access in and easy street pick up for Ubers. We had a nice time and felt comfortable.
Superhost
Home in Chicago
5 out of 5 average rating, 6 reviews

Perfect Location Across from Park & Train Station

CarlaRating, 5 stars3 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.
Top guest favourite
Home in Chicago
5 out of 5 average rating, 10 reviews

Exquisite Chicago Modern Rooftop, Sleeps 9

MuhammadRating, 5 stars1 week ago
The whole process was very easy
Top guest favourite
Home in Oak Park
4.98 out of 5 average rating, 96 reviews

Modern Victorian Charm | A+ Location in OP

SamRating, 5 stars1 week ago
Great place to stay while visiting family! Very kid friendly and baby items provided too! Loved this home away from home!
Top guest favourite
Home in Chicago
5 out of 5 average rating, 74 reviews

Windy City White House (3br/2ba) *New Listing*

SamanthaRating, 5 stars1 week ago
Beautiful place! Very clean! The host was very responsive. The kitchen was stocked with tea, coffee and extras. I love that they had a tea kettle. The rental had everything we needed, extra bedding and towels. We arrived to a basket of snacks and drinks 😊. Comfy beds and sofa in the sitting room. Lots of room for a family of 4. It is an upstairs unit so stairs to climb. Location was ok.
Superhost
Home in Cicero
4.71 out of 5 average rating, 276 reviews

Close2city 3 bedroom with private parking (MDW)

RubinaRating, 5 stars2 weeks ago
Daniel was very responsive and accommodating. The private parking was great and the neighborhood was close enough to get into the city with ease.

Private house rentals

Guest favourite
Home in Chicago
4.88 out of 5 average rating, 51 reviews

CasaNova Modern City Living

HelenRating, 5 stars1 month ago
Beautiful home layout and very spacious! Location was a quick drive to the city, which was convenient. Host was also very kind and attentive. Thank you Ms. Lilly for our stay!
Guest favourite
Home in Chicago
4.93 out of 5 average rating, 28 reviews

1mi to Beach | 2-Floor Loft | Foosball

MarcelloRating, 5 stars2 weeks ago
The stay was amazing. The only issue was finding parking especially at night was really tuff to find a stop.
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.
Guest favourite
Home in Berwyn
4.91 out of 5 average rating, 22 reviews

European Custom Built Home 2 Bedrooms

DonRating, 5 stars1 month ago
What a really nice home! My crew and I were very thrilled to stay in this home. Large areas everywhere. Bedrooms were large and beds were comfortable. Very proactive host and quick to respond. We could not be more satisfied with our stay and look forward to returning if the home is available. We were close to several restaurants and could walk to them wothing 10 minutes. Safe neighborhood.
Guest favourite
Home in Chicago
4.94 out of 5 average rating, 18 reviews

Modern Single-Family Home w/outdoor space + garage

FrancescaRating, 5 stars2 weeks ago
We had a wonderful stay at this Airbnb! The space was perfect for our whole family—spacious, clean, and very comfortable. It had everything we needed to feel at home. The host was incredibly helpful and responsive, always willing to accommodate any needs or questions we had throughout our visit. The location was also great—easily accessible to a variety of activities, restaurants, and attractions in the area. We truly enjoyed our time here and would definitely stay again, especially with a large group. Highly recommend!
Superhost
Home in Chicago
4.64 out of 5 average rating, 59 reviews

Fully Renovated! only 15 min away from Downtown!

MidgeRating, 5 stars1 month ago
Very clean apartment and host was great. Everything was just as described and I would recommend it to a friend.
Guest favourite
Home in Chicago
4.98 out of 5 average rating, 64 reviews

① Lux | Spa | Rooftop | Modern | 4 Mi to Downtown

DaisyRating, 5 stars1 week ago
Anita’s place was absolutely stunning and looked just like the photos. Extremely clean and very spacious. We hosted a 50th birthday brunch here and it was more than enough space and amenities to accommodate everyone. The rooftop was just amazing and a great addition to the place. Thank you Anita for letting us book your gorgeous home and we would love to book again and again! ⭐️⭐️⭐️⭐️⭐️
Top guest favourite
Home in Chicago
5 out of 5 average rating, 89 reviews

Architect's Urban Oasis | 4bd/3ba I Luxe

KristanRating, 5 stars1 week ago
Beautiful home with high-end furnishings and gorgeous amenities. The house is spotless and the beds were extremely comfortable. My family had a wonderful time celebrating my son’s UChicago graduation in this very special home. Highly recommend!

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