
Vacation rentals with beach access in Woodlawn, Chicago
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Top-rated beach access rentals in Woodlawn, Chicago
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Popular amenities for Woodlawn, Chicago beach access rentals
Apartment rentals with beach access

Spacious! 3 bedroom apartment in Edgewater!
Great place. Spacious, clean, quiet. If this is the neighborhood you're looking for then this is a aces.

The Lakefront Lookout (2BR)
We had a great stay!

Woodlawn Oasis
Super responsive host and I loved the candles they had! The place was super clean and is exactly how it is listed on the photos

Lincoln Park DePaul Rowhouse Historic Bissell St
Nancy provided great instructions for check in and even saved us a parking spot in the street when we arrived. She was very proactive with communication during our stay to make sure we had everything we needed. The property was cleaning and welcoming.

Andersonville apartment, walk to the lake & train
Highly recommend staying at this beautiful home in Andersonville. Liz stands out as the top of the top AirBNB hosts. She’s thought of everything to make you feel at home, from a welcome note and snacks at arrival, wonderful suggestions on what to explore in the neighborhood and city, to an incredibly simplified checkout process. Easy parking and close proximity to local grocery store and charming restaurants. Cannot rave enough about our family’s wonderful experience. Would love to stay again!

Spacious 2 Bedroom in the heart of Lakeview!
Very comfortable space; great location; helpful host; well-equipped. Of note, there is no thermostat within the space, but that did not present an issue. Would return without hesitation in the future.

Quiet city getaway by beach in fun neighborhood
We had an amazing stay at their cozy and quiet place! Very responsive, helpful and provided great guides to local transportation and restaurants! Would love to stay again for our next Wrigley Field event!

Beautiful Hollywood-Ridge Suite in Edgewater
Dorothy was lovely and my stay at her place was exactly what I needed. The apartment is clean and well appointed. Location is great - walkable to Rivendale Theatre and lots of restaurants. Would definitely stay with Dorothy again if my travels take me back to this part of Chicago.
House rentals with beach access

Cornerstone - Mins from Downtown & Lake Michigan
Angela’s place is amazing. As a host she is extremely responsive and went above and beyond to address anything that I asked about. I l love the primary bedroom because it’s large and the bed is really comfortable. My husband enjoyed the jetted tub.l in the upstairs bathroom. We also made great use of the workout room (my husband did). The open concept first floor suited my family needs well. Overall we enjoyed our stay and are appreciative of Angela for being a great hostess!

Quiet and welcoming house.
Truely a home away from home. We had our family go together for the holidays and booked the place for two weeks. Tsegie's place has everything in there and plenty of space. It has clean linens, towels and utensils including for baking. Only confusion was with regards to the pet as there is a fee for having a pet (dog). Since we didn't list the dog in our booking, there was a bit of clarifications to be sent back and forth before we settled it down amicably. Overall, an excellent place for family and friends gathering.

Amazing historic campus mansion!
Excellent host, beautiful house.

House 5BED/3BATH/1PARKING close to Downtown & Lake
This home is in a quiet neighborhood. It is close to a Target awesome. Easily walkable to Andersonville and Clark St. for many restaurants and shops. The home itself was spacious, beautiful, and very clean. Junni was responsive to our inquiries.

CasaNova Modern City Living
Lilly was prompt in her responses and very helpful. The place was well kept and clean. A quick Uber ride to downtown. Our group really enjoyed our stay!!

Gated 3 Story Home perfect for Group Travelers
I've stayed in a lot of Airbnb's, & dont even have words to describe how much i loved staying here. Two friends & i were in town for a wedding & looking for someplace warm, relaxing, and away from all of the commotion. We could not possibly have chosen better. The house had everything we needed, & was so beautifully decorated -- the pictures do not do it justice. The only thing more lovely than the house was the garden -- it is this perfect little Eden. Gleatha was helpful, flexible, responded at once to questions, and checked in a couple of times, which was so much appreciated. I seriously wanted her to be my best friend by the end of the trip. We did not have time to explore the neighborhood, but the parts we did see were safe and lovely. Also much closer to downtown than we expected. This is not a house to which i would bring small children, as some of the decor is fragile. For everyone else, you would be fortunate indeed to stay here. Thank you again, Gleatha.

Exec Lux home wth 3 Level,6 Bdrms/3bth & 2 Kitchen
This is a Beautiful Home, with a peaceful atmosphere. A Great place to walk into and relax after a long trip, and spacious enough for a small group to enjoy one another's company without feeling overcrowded. 2 Full Refrigerators and 2 Full size stoves makes this location a rare find.

Cozy 4-Bedroom House with Patio
One of the best host we have ever stayed with!!
Condo rentals with beach access

A Stones Throw from U Chicago South Campus!
Had a great stay! The place was super clean and cozy, and the host was super helpful and easy to communicate with. Would totally stay here again!

Spacious Evanston Duplex - Free Parking
The home is extremely spacious and located w/in walkable distances to restaurants and shops in Evanston IL. Very modernized and kept cozy warm with steam heat. We had 4 adults and a dog staying there and we had plenty of room to spread out. We also entertained and easily accommodated 8 extra people for dinner. The selection of toys for children were also very helpful. Thank you for sharing this place with us over the holidays!

The Ramblers Inn, Northside NEW Reno w/parking!
We had a wonderful, peaceful time staying with Jeremiah and Maysa. They were kind, extremely communicative, and when our family came over to visit everyone commented on what a beautiful home it was. 10/10. Also, extremely fast WiFi, great for working from home for multiple people who were on video calls.

Jarvis Gardens - 1BR/BEACH/Wine patio/fire pit
I recently had the pleasure of staying at this charming Airbnb, and I can't say enough good things about it! From the moment I walked in, I was blown away by how beautifully decorated the space is. Every corner is thoughtfully designed, making it feel both cozy and stylish. The host was incredibly responsive and quick to answer any questions I had, which made my stay even more enjoyable. It’s always nice to know that help is just a message away! The location is fantastic—perfectly situated to explore the local sights and hidden gems. I loved being able to step out and find great restaurants and shops within walking distance. One of my favorite features was the record player! It added a nostalgic touch to my mornings and evenings, allowing me to unwind with some great tunes. And let’s not forget about the shower—it was absolutely breathtaking! It felt like a spa experience every time I stepped in. Overall, this Airbnb exceeded my expectations, and I can’t wait to return! Five Stars!

2BD/2BA MAG MILE MASTERPIECE (+Rooftop)
It was just like the photos. If we ever had any questions they would answer immediately. Super nice, the whole family loved it! If we ever go back to the windy city we would stay again.

Pets OK | Walk Score 95 | Desk | 1,750ft² |W/D
Perfect spot in Lincoln Park! My sisters and I loved our stay at Danny's place. The apartment was spotless and well-stocked, with plenty of space for the five of us. Check-in/apartment access could not have been easier! Will definitely try to stay here again.

Andersonville: 3-bed, 2-bath w/ Dining RM & EZ PKG
We enjoyed staying at Ari's place while visiting Chicago. Foster Avenue is a busy road but we were pleasantly surprised at the availability of parking and lack of traffic noise. It's a great place to stay.

Large 2BR, 2BA, patio, sunroom, W/D, L-kitchen
Pablo’s place was in a great area easy walk to the L train, friendly people around the neighborhood, easy access to stores, restaurants, grocery store. His home was beautiful very comfortable and had a lot of thoughtful amenities not listed and made it for a great experience. Although the weather was a little crazy we made use of the patio. A lot of personal touches in the home. We would definitely stay again. Thanks for the hospitality.
Quick stats about vacation rentals with beach access in Woodlawn, Chicago
Total rentals
20 properties
Nightly prices starting at
$30 before taxes and fees
Total number of reviews
940 reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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