House vacation rentals in West Side

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Popular amenities for West Side house rentals

House rentals with a pool

Guest favorite
Home in Glen Ellyn
4.83 out of 5 average rating, 6 reviews

Pardizes Suites

RayRating, 5 stars1 day ago
Lisa was the best host I've ever had. The house was amazing. Definitely #1 against every other AIR BNB I've ever stayed at before. This house was comfortable, up to date (if not ahead of its time). The atmosphere was great. The beds were comfortable. There was so much to do in that home. I honestly will do my best to stay in this home again in the future. Outstanding job Lisa. See you soon!!! Rated 10 stars.......
Guest favorite
Home in Glen Ellyn
4.95 out of 5 average rating, 20 reviews

Glen Ellyn Home

TimothyRating, 5 stars5 months ago
The property was very nice. It was well maintained and our family with our grandson were very comfortable. If we were to have a negative comment is that the heat distribution was not even throughout the home. The upstairs where the three bedrooms were located was very warm and the kitchen, living room and family were quite chilly. However, this did not impede us having a comfortable stay.
Guest favorite
Home in Munster
5 out of 5 average rating, 10 reviews

Munster hide away

ChristopherRating, 5 stars4 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.
Home in Schaumburg
4.8 out of 5 average rating, 10 reviews

Spacious 3 Floor Townhome

FranciscoRating, 5 stars1 week ago
good place to stay. kid frendly. close to all activities y had planned
Top guest favorite
Home in Bloomingdale
4.94 out of 5 average rating, 48 reviews

Whole House With Hot Tub And Spacious Bedrooms

KarinaRating, 5 stars3 weeks ago
Amazing stay! This place has everything you need for both short and long visits. The location is extremely safe and convenient with shops within walking distance. My family and I thoroughly enjoyed the entire property, especially the game room and TV room which were perfect for entertainment. Moiz, the host, was very kind and quick to respond to any needs we had. Thank you for everything! We would definitely stay here again
Guest favorite
Home in Schaumburg
4.91 out of 5 average rating, 22 reviews

Schaumburg Oasis with a Pool and Hidden Garden

GotimukulRating, 5 stars4 weeks ago
had such a wonderful stay! The place was exactly as described—clean, cozy, and beautifully maintained. The host was incredibly kind and responsive, making the whole experience smooth and stress-free. Would definitely stay here again and highly recommend it to anyone looking for a comfortable and welcoming place to stay!
Guest favorite
Home in Plainfield
4.94 out of 5 average rating, 77 reviews

Large Spanish style Home (w/inground pool)

BethanyRating, 5 stars1 week ago
Stayed here the night before my wedding with my siblings who stayed the night of the wedding. We hosted our getting ready portion here for the morning of the wedding and Olinka and Daniel were gracious enough to allow us to stay in their beautiful home. Made for gorgeous pictures and a comfortable stay both nights. Thank you!!
Home in Glenwood
4.8 out of 5 average rating, 56 reviews

Spacious Family Glenwood Estates Home w/ Hot Tub!

Nicole And ArnoRating, 5 stars1 month ago
Loved this Airbnb! Didn’t want to leave.

Weekly house rentals

Guest favorite
Home in Chicago
4.92 out of 5 average rating, 282 reviews

Duplex Home RoscoeVillage/Wrigley Free St Parking

MontiraRating, 5 stars1 week ago
2nd time staying at Sharleen’s place—wonderful experience! We like location, friendly and quiet neighborhood, walkable to restaurants. We would recommend to guests looking for a space in Roscoe. 🙂
Guest favorite
Home in Chicago
4.98 out of 5 average rating, 152 reviews

Spacious Five Bedroom Home in Trendy Chicago Neighborhood

Kevin And CourtneyRating, 5 stars2 months ago
Great experience at Casey’s place. The home is as well stocked with kitchen essentials and extras as any place that we have ever stayed. There were toys for the kids and the design of the place was awesome. We had a great stay and would definitely come back.
Guest favorite
Home in Lansing
4.82 out of 5 average rating, 117 reviews

Cozy at The Walter

JodimarieRating, 5 stars4 weeks ago
Lovely cozy home perfect for what we needed. Loved the yummy extras she left for us in the kitchen:) The beds were comfortable and there were plenty of extra comforters for the cold nights! The heater worked amazingly well and the home smelled so nice of mild sandalwood from a diffuser in the living room. We felt right at home, and the location for us worked out well! Thank you!!
Guest favorite
Home in Chicago
4.86 out of 5 average rating, 221 reviews

The Avondale Guesthouse

ErickaRating, 5 stars6 months ago
We absolutely loved the place! Great location, price and space! Jed was so kind and responsive, and we absolutely loved the the outdoor space! We would definitely stay again!
Guest favorite
Home in Whiting
4.84 out of 5 average rating, 153 reviews

The Spa of Downtown Whiting

YesyRating, 5 stars2 weeks ago
Thank you for allowing us to enjoy your home. It was a wonderful experience. It is incredible. The place is very cozy. You feel an atmosphere of relaxation and peace.
Top guest favorite
Home in Chicago
4.95 out of 5 average rating, 185 reviews

Wrigleyville Greystone

RichRating, 5 stars1 week ago
If you going to Wrigley Field this is a great location to stay in, Walkable to the ballpark.
Guest favorite
Home in Justice
4.93 out of 5 average rating, 224 reviews

3 Kng, 1 Qn, 1 Full, 3AirBd|Basktbll Crt|FreePrkin

PaulRating, 5 stars2 months ago
Great place with plenty of space. Our family really enjoyed Michael’s home.
Guest favorite
Home in Chicago
4.95 out of 5 average rating, 216 reviews

Paradise on the Park

JoannaRating, 5 stars6 days ago
Great cozy place to stay. Right across from a park and super quiet. Walkable to many restaurants and public transportation. It had every amenity including a washer and dryer. The shower is huge and the bed comfortable. Ryan’s communication was fast and precise. Would definitely stay there again!

Private house rentals

Top guest favorite
Home in Oak Park
5 out of 5 average rating, 5 reviews

Sleeps 12 Comfortably in 8 Bedrooms 3 Full Bath

VinceRating, 5 stars4 months ago
This is the 2nd time this year we rented from Michael. He continued to impress with the responsiveness. This time we filled the whole house, all bedrooms and both floors, 12 in total, mix of kids and adults. We decorated for Christmas, made it feel like we were home for the holidays. We walked all around the neighborhood, got coffee in the morning, fresh bread from a fabulous bakery in Downtown Oak Park and always felt safe and enjoyed the friendly neighborhood. The home and bedrooms were warm when you wanted them warm during the day and cool at night to sleep in. Kitchens were well equipped and all the appliances worked perfectly. The tankless water heater was a blessing when we were all trying to get out for a family event. At one point we realized that we were out of trash bags on Christmas morning. Michael had them there in less than 30 minutes. Over the top responsiveness. Being 10 minutes from the Eisenhower makes this convenient to either Downtown or Oak Brook.
Superhost
Home in Chicago
4.86 out of 5 average rating, 102 reviews

Casa PLZN Location | Entire Home | Garage Parking

AuraRating, 5 stars2 weeks ago
Happy that this place was available! It was comfortable, clean, and roomy, right in Pilsen. Excellent communication and overall great spot.
Top guest favorite
Home in Elmhurst
5 out of 5 average rating, 48 reviews

Big Family Home with 4 King Beds

GabrielRating, 5 stars1 week ago
I will be recommending this place to everyone for a nice get together. The neighborhood was nice and quiet and it is a beautiful place to relax or to have as an activity weekend. Plenty of stuff to do
Superhost
Home in Blue Island
4.82 out of 5 average rating, 195 reviews

Warm and comfortable inviting Suburban home !

CasieRating, 5 stars1 week ago
Nice spot - place was very clean, comfy beds, lots of seating areas that were also comfy. We got used the the sounds of the trains after the first night. Bumped into Rich one day while he was mowing the grass; he was very kind. The place is a little older, but that’s in the description. We couldn’t figure out how to get the stove to turn on so we heated food in the microwave and on the gas grill outside. Neighborhood was very quiet and peaceful, and we liked having the fenced yard for our dog.
Superhost
Home in Gary
4.87 out of 5 average rating, 47 reviews

The Blue House: Family Retreat

MichaelRating, 5 stars2 days ago
We enjoyed our stay at this house . She was very responsive and she made good use of space in the house to accommodate a family. Would recommend to anyone.
Superhost
Home in Markham
4.73 out of 5 average rating, 124 reviews

The Country Life! Entire House.

DeniseRating, 5 stars1 month ago
Cathy was a great host, very responsive! House was great, it accommodated our family size perfect. The only thing in my opinion that was missing was washer and dryer access in the home. We were traveling with toddlers and couldn’t wash a load of clothes. But aside from that everything else was great.
Guest favorite
Home in Chicago Ridge
4.92 out of 5 average rating, 127 reviews

Quiet cul-de-sac with huge fenced in backyard

JonathanRating, 5 stars3 days ago
Great experience. Tom is a great host , replies super fast and offers to help with anything needed , the house is spacious and everything is well kept.
Superhost
Home in Chicago
4.84 out of 5 average rating, 503 reviews

*ENTIRE CITY HOUSE/PARKING - 3 MIN WALK TO TRAIN

AdelaidaRating, 5 stars5 days ago
Nice place, quiet and comfortable and we loved the neighborhood

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