House vacation rentals in Woodlawn, Chicago

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Popular amenities for Woodlawn, Chicago house rentals

House rentals with a pool

Home in Glen Ellyn
4.8 out of 5 average rating, 5 reviews

Pardizes Suites

FernandaRating, 5 stars1 week ago
Really nice and spacious place. Everything was clean and comfy.
Guest favorite
Home in Schererville
4.94 out of 5 average rating, 52 reviews

Cozy house in Schererville

CarlosRating, 5 stars1 week ago
Kate’s place was exactly what I expected. Pristine condition and spotless. Kate accommodated my early arrival which was greatly appreciated. I would 100% book this place again. Highly recommend her place to anyone in the area for a weekend or just to get away from the city. Thank you again for your attention on such a short notice on my booking.
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.
Home in Olympia Fields
4.56 out of 5 average rating, 43 reviews

Luxurious South Suburban Villa

LanceRating, 5 stars3 months ago
My team thanks you for your comfortable home, it is what the crew needs after a day working outside on a large solar field array. Whenever on an extended out of town work trip we like to stay at an Airbnb, a much better value than several rooms at hotels. Your home was roomy & comfortable, we enjoyed our stay and thank you for being a great host.
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 Lockport
4.63 out of 5 average rating, 8 reviews

Hidden GEM OASIS in Chicagoland

Raymond BrianRating, 5 stars4 weeks ago
Excellent host! Fantastic property!
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 stars2 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
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 Roscoe Village
4.92 out of 5 average rating, 282 reviews

Duplex Home RoscoeVillage/Wrigley Free St Parking

MontiraRating, 5 stars4 days 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 Glen Ellyn
4.92 out of 5 average rating, 148 reviews

Home in Glen Ellyn

LindaRating, 5 stars4 days ago
Humongous place to stay for a large group. Master bedroom was so huge! Having 5 bedrooms was great. We really enjoyed our stay.
Guest favorite
Home in Lansing
4.82 out of 5 average rating, 117 reviews

Cozy at The Walter

JodimarieRating, 5 stars3 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!!
Top guest favorite
Home in Wicker Park
4.97 out of 5 average rating, 33 reviews

Wicker Park 6bd/4ba, Steps from Cta, Parking Incl

LaureenRating, 5 stars1 month ago
The location alone makes this home worth booking. Add that there’s ample room for family/friends and it’s a gem in the middle of a great Chicago neighborhood. We were a group of six and loved every minute.
Guest favorite
Home in Avondale
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 Lake View
4.95 out of 5 average rating, 184 reviews

Wrigleyville Greystone

ThomasRating, 5 stars1 month ago
Fantastic place in an awesome location. Very walkable part of town and a great spot to easily get to Wrigley Field. Found a number of great bars and restaurants in walking distance during our stay. Would definitely stay here again!
Guest favorite
Home in West Town
4.95 out of 5 average rating, 214 reviews

Paradise on the Park

LyndsayRating, 5 stars1 month ago
One of the best Airbnb’s I have stayed at! Super clear instructions, clean, modern, and a great location! I would definitely stay here again! I even had the opportunity to buy a piece of his original artwork 😊 The Airbnb is beautifully decorated in many of his original pieces and I was ecstatic to find out there were available to buy! Very communicative and friendly.

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 Illinois Medical District
4.86 out of 5 average rating, 101 reviews

Casa PLZN Location | Entire Home | Garage Parking

RicardoRating, 5 stars2 weeks ago
Great place! I’ll definitely be coming back! The beds are amazing!
Top guest favorite
Home in Elmhurst
5 out of 5 average rating, 48 reviews

Big Family Home with 4 King Beds

GabrielRating, 5 stars5 days 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 Austin
4.88 out of 5 average rating, 48 reviews

Grand Victorian Mansion in Austin Area

SaifRating, 5 stars6 months ago
The accommodation was spacious and very comfortable for our large group of 16. While the floors creak a bit, it wasn’t an issue. Samantha was always quick to address any questions and issues. The gated parking area provided ample space for our cars, which was a great convenience.
Superhost
Home in Blue Island
4.82 out of 5 average rating, 195 reviews

Warm and comfortable inviting Suburban home !

CasieRating, 5 stars4 days 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, 45 reviews

The Blue House: Family Retreat

AlexisRating, 5 stars1 week ago
Clean and kid friendly! Just as described. Perfect place to hang our Easter vacation with our group of 13!! Everyone felt comfortable and accommodated. Only thing I’d change if I could, more pillows! We’re a pillow loving family. Otherwise everything was great!!
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.
Top guest favorite
Home in Chicago Ridge
4.92 out of 5 average rating, 126 reviews

Quiet cul-de-sac with huge fenced in backyard

CandaceRating, 5 stars1 week ago
Tom’s place felt right at home! Spacious backyard, quiet neighborhood, and he’s very friendly. Responded right away with any questions or comments we had! 10/10 recommend anyone to stay here if available!

Quick stats about house rentals in Woodlawn, Chicago

  • Total rentals

    60 properties

  • Nightly prices starting at

    ﺩ.ﺇ110 before taxes and fees

  • Total number of reviews

    1.7K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    60 properties include access to wifi

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