
Holiday rentals with beach access in Woodlawn, Chicago
Find and book unique accommodation with beach access on Airbnb
Top-rated Accommodation with Beach Access in Woodlawn, Chicago
Guests agree: These holiday homes with beach access are highly rated for location, cleanliness and more.
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Popular amenities for Woodlawn, Chicago Accommodation with Beach Access
Apartment rentals with beach access

Spacious! 3 bedroom apartment in Edgewater!
Awesome apartment in the Loyola Chicago neighborhood. Easy access to the loop with the red line. Host is super responsive. The place was spotless and well stocked when we arrived.

The Lakefront Lookout (2BR)
Great place, and area. The place was clean and very spacious!

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 2 bed with modern kitchen + bath
Our second stay with Michael and Lora was just as great as the first one. It's a great space for couples or small families. Very well appointed, it offers everything you could need, and is in the best neighborhood -- a major plus! This is our go-to place to stay when we come to Chicago.

Pristine Lakeview| Boystown |Wrigley Haven |Beach.
Wonderful stay in a beautiful part of Chicago! There's lot to do in the area and it's just a quick walk away from the lake shore. Would highly recommend for anyone looking for a clean and cozy place to stay in northern Chicago!

Sunny Modern 1BR Beach/City Views Rooftop WFH Gym
The place was almost perfect. The Walls are very thin so you can hear everything other than that not bad at all oh and find the SERK art this is an insider for those who will pay attention at their stay.

Spacious 2 Bedroom in the heart of Lakeview!
Beautiful boho, whimsical space, firm mattresses, all the comforts of home: extra blankets, pillows, towels, books and magazines. Took pictures of how pretty everything was, thinking I want my home to look like this. Toilet flush was tricky in the way of older homes. Super convenient, in a fun neighborhood and easy walk to public transportation, parking available. We had a great time.
Holiday 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!

Amazing historic campus mansion!
An amazing host, went above and beyond to accomodate for our needs (we needed to leave bags in the house later than check out, which she allowed and we are very thankful for) - a beautiful house in a beautiful neighbourhood! Highly recommend :)

House 5BED/3BATH/1PARKING close to Downtown & Lake
The home is well maintained, very clean, with great amenities. I appreciated that Junni reached out to me before the trip to clarify any questions and provided detailed instructions for everything. I will be returning! Thank you Junni!

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!!

Woodlawn Oasis: 5-15 Mins from Food, Fun, Dining
Good location restaurants and shopping not far. House was clean, great space and provided the basics. First night wasn't working the host responded immediately and was able to troubleshoot and fix the issues!

Private Downtown Retreat with Rooftop Oasis
Perfect location and plenty of space for our party. It was the first time to Chicago for most of the guests and it was the perfect introduction to the city. Florin was accommodating and made sure everything was great for us. Clean, spacious, and priced fairly. Strongly recommend.

Edgewater Beach Home Steps to the Lake
This place was great!!! Clean and LOTS of space. We barely left the house except to grab a few meals and it was great! The deck was so nice (we got lucky on weather) and the kitchen was super well stocked!! Would highly recommend!
Holiday condos with beach access

A Stones Throw from U Chicago South Campus!
Great location within walking distance of University of Chicago and in a safe neighbourhood. Basement apartment with 2 bedrooms. Bed was comfortable & extra pillows & blankets were provided. Toilet & kitchen facilities were slightly dated but functional. Appreciated the use of washer/dryer & complimentary coffee/tea. Very hospitable host!

Studio flat in the heart of Chicago's Gold Coast
This is our second stay here. the location can't be beat and we will continue to stay here when we are in chicago. I will note that it is VERY loud. Depending on who you have above you can make it even louder. the pipes for the heat are also extremely loud. This doesn't bother us so much as we go in expecting it. This is also not the fault of the host at all and this airbnb and host are both still great!

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)
WWWWOOOWWW!! This host team was EXCEPTIONAL! I’ve stayed in plenty of AirBnBs, and I’ve NEVER encountered a host that was so EXTREMELY accommodating, responsive, and kind! Other hosts should take a page out of their book! The only thing I would change, and it’s not a bad thing (just a matter of preference); I would have some type of blinds or drapes over the living room windows. This will allow for privacy when you’re sitting in the living/dining room areas at night with the lights on inside. Hands down, we would without a doubt book with this team again! Thank you Wendy, Matt, and your co-hosts for helping to make our time in Chicago wonderful!

Pets OK | Walk Score 95 | Desk | 1,750ft² |W/D
Great stay!! Perfect location and it suited our family and dogs wonderfully while we weee in Chicago for 4 nights. I passed this listing along to a friend who is looking to stay in the same area. Overall great experience and we loved our time there!

Andersonville: 3-bed, 2-bath w/ Dining RM & EZ PKG
Just as described. Easy walk to transit, restaurants, coffee shops and more. Slept 5 of us easily and comfortably. Clean and updated space with plenty of amenities. As well, the host is great with communication. Would absolutely stay here again.

Large 2BR, 2BA, patio, sunroom, W/D, L-kitchen
This was the most amazing stay!!! I was coming home to visit friends and family and this apartment was beautiful and spacious - will definitely be staying again in the future.
Quick stats about holiday rentals with beach access in Woodlawn, Chicago
Total rentals
20 properties
Nightly prices starting at
$47 AUD before taxes and fees
Total number of reviews
950 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wi-Fi availability
20 properties include access to Wi-Fi
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Shedd Aquarium
- Guaranteed Rate Field
- Frank Lloyd Wright Home and Studio
- Humboldt Park
- The Field Museum
- Wicker Park
- Lincoln Park Zoo
- Museum of Science and Industry
- Six Flags Great America
- Skokie Country Club
- Promontory Point
- 875 North Michigan Avenue
- Flossmoor Golf Club
- Odyssey Fun World
- Moraine Hills State Park
- Washington Park Zoo
- Chicago History Museum
- Chicago Golf Club
- The 606
- Lincoln Park