
House holiday rentals in West Side
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Top-rated house rentals in West Side
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Popular amenities for house rentals in West Side
House rentals with a pool

Pardizes Suites
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

Munster hide away
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.

Rosemont 4BD2BA house with Pool
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!

Now Open: Heated Pool with Entire House
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.

Schaumburg Oasis:Private Pool & Enchanted Garden
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!

Luxury fenced in modern ranch
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!

LUXURY - Movie Theater + Spa House
Great getaway place to stay at. Beautiful patio area as well!

Spacious 4 Bed/3.5 Bath Sleeps 8+
Beautiful house very clean and comfortable. We'll be back very soon
Weekly house rentals

City Cottage in Logan Square-Avondale
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!

NEW! 3BR/2.5B Duplex in Noble Sq
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.

Spacious | 3 Beds | Free St. Parking
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.

Perfect Location Across from Park & Train Station
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.

Exquisite Chicago Modern Rooftop, Sleeps 9
The whole process was very easy

Modern Victorian Charm | A+ Location in OP
Great place to stay while visiting family! Very kid friendly and baby items provided too! Loved this home away from home!

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

Close2city 3 bedroom with private parking (MDW)
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

CasaNova Modern City Living
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!

1mi to Beach | 2-Floor Loft | Foosball
The stay was amazing. The only issue was finding parking especially at night was really tuff to find a stop.

Sunny Historic Cottage on the Park
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.

European Custom Built Home 2 Bedrooms
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.

Modern Single-Family Home w/outdoor space + garage
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!

Fully Renovated! only 15 min away from Downtown!
Very clean apartment and host was great. Everything was just as described and I would recommend it to a friend.

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

Architect's Urban Oasis | 4bd/3ba I Luxe
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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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Six Flags Great America
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Lincoln Park Zoo
- Wicker Park
- Illinois Beach State Park
- Brookfield Zoo
- Washington Park Zoo
- The 606
- The Beverly Country Club
- Flossmoor Golf Club
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