
Holiday rentals with lake access in Woodlawn
Find and book unique lake access rentals on Airbnb
Top-rated rentals with lake access in Woodlawn
Guests agree: these rentals with lake access are highly rated for location, cleanliness and more.

The Spa of Downtown Whiting
so close to Chicago but so far away. NEWLY REMODELED AND COMPLETELY FURNISHED. There's so much to enjoy in this incredible converted 2 flat, now a single unit. WE COMPLETELY RIPPED ON AND REDID THE ENTIRE INTERIOR. 1ST Flr-spa w/ 2 person jacuzzi, shower, continuous hot water, family room, kitchen 2nd flr, sitting room w/ TV and surround sound, 2 bedrooms, w/ bathroom and bath/shower. -FRONT BALCONY, -SPEAKERS THROUGHOUT -BLOCKS FROM THE BEACH & WOLFE LAKE -PERFECT LOCATION FOR PIEROGIFEST

Lincoln Pk-parking-wifi-King bd-crib-kid friendly
This wonderful 2 bedroom garden apartment in superhot Lincoln Park on a block where homes sell for 4 million to 12.5 million dollars. Walk score 97 The apartment was totally renovated adding new furniture, Flatscreen TVs in both bedrooms and Livingroom, a fully stocked kitchen, superfast wifi (150 Mbps) dedicated parking space, rooftop deck, washer, and dryer inside the apartment, see all that is offered below. The train (EL) stop is 2.5 blocks from the apartment. Go to the Cubs game/downtown.

420 at Cheltenham 4BR
If you want to experience an authentic piece of Chicago and it’s rich history, our place is a cozy spot to start and it’s just like being at home. Summertime Chicago Lake Shore Drive Beaches. Lollapalooza. Chicago Riverwalk. Concerts at Soldiers Field-Bears. Winter wonder festival. The Bean. Great for larger groups visiting looking to divide costs. Obama Library, Southshore golf course, Reggies on the Beach, Shedd Aquarium, Field Museum, Museum of Science & Industry are all within 20 minutes.

Wrigleyville Condo 2 Blks from Lake & Train
I think you'll enjoy my spacious East Lakeview condo. The location is super convenient just 2 blks from Sheridan red line & 2 blks from the lake. Easy proximity 4 blks to Wrigley Field & restaurants/nightlife in Wrigleyville & Boystown. Amazing restaurant next door w/back patio- El Mariachi w/the freshest chips & guacamole! Starbucks, playground, and Divvy Bike station at the corner. 1 mi to Montrose Beach. All downtown sight-seeing easily accessible from Lake Shore Dr or red line 2 blks away.

Spacious 4-Level/4-Bedroom Townhouse in West Loop
Spacious Townhouse in Chicago's Hip Foodie Neighborhood: West Loop/Fulton Market. This is a Private, 4-Story Townhouse on a Tree-Lined Street just Steps from the Action...while still quiet enough for a good night's sleep. Walk to some of the Nation's Top Restaurants (near Restaurant Row), Clubs, Pubs, Groceries, Parks, Coffee Shops. Easy Train Transit to O'Hare, Navy Pier, Mag Mile, McCormick Place, etc...Terrace w/Skyline Views & Attached Garage Parking for 1 Regular-Sized Vehicle Included!

Remodeled, Near Loyola, Beach and Subway
Stylish and sophisticated, this remodeled 3 bedroom, 2 bath private apartment is in a prime location, 3 blocks from Hartigan Beach, and 2 blocks to the Loyola Red Line "L" station to take you to Wrigley Field, downtown & many locations in between. We are 2 blocks from Loyola University & about 4 miles to Northwestern University. Located on a quiet, residential tree-lined street, we are a 2 block walk from all manner of restaurants & conveniences associated with our proximity to Loyola.

RockStar Pad W3A BoysTown/Wrigley Field/Parking lot
HAVE IT ALL @ W3A Chicago Wrigley Field/Boystown/Lakeview -Newly renovated like new in safe centrally located East Lakeview. -10 min walk to Wrigley Field, Boys town, beaches, super markets, restaurants with late night dining. 5 min walk to Metro Sheridan Red Line (direct downtown), private enclosed parking $10/night & or free permits for street parking -600 thread count linens, fluffy soft pillows, house coats, high speed WiFi, Sonos speakers, stylish design & in unit washer & dryer

Downtown Park #11 - Mich Ave PH | gym+rooftop
Feel at Home, Unwind, and Enjoy the amenities you deserve when you come to Chicago! Guests love staying with us because: -Central Location on Grant Park (no car needed!) -FAST WIFI -En-suite Laundry -Did we mention the Lake & Park are outside our front door? -Comfy Queen bed -Loft style bedroom -Shared Rooftop Deck stunning views -Gym -3 blocks from Red "L" subway -Close to Grant Park, The Bean, Soldier Field, Museums If you are looking for a special place, you've found it!

Chic Lincoln Park Townhome | Rooftop + Glam Bar
⭐️ Lincoln Park Luxury | Rooftop + Glam Station | Sleeps 10 ⭐️ Stay in the heart of Lincoln Park, one of Chicago’s most vibrant neighborhoods, where tree-lined streets meet world-class dining, shopping, nightlife, and the lakefront. This beautifully curated 3-story townhome blends luxury, comfort, and style, making it ideal for bachelorette weekends, girls’ trips, family stays, and celebratory group getaways. 📍 Steps from Lincoln Park Zoo, cafés, boutiques & the lakefront

Modern Corner 2BR in Streeterville | Roof Deck | L
Stunning 1,200 square foot apartment with oversize windows, an open layout, and city/lake views in multiple directions. This bright and modern two bedroom, one bathroom corner unit is perfect for travelers looking for a stylish escape in the sky in downtown Chicago just off the Magnificent Mile and the lakefront. The building has great amenities including an amazing rooftop terrace with 360 degree views of the skyline and the lake. This is the best location in the city!

Chicago Bootlegger House Sleeps 10-20
Walk to restaurants, groceries, shopping, Wrigley Field, Lake Michigan, Beaches, Boat Harbor, Lincoln Park Zoo, night life, bars, clubs, Red Line Train, Lakeshore Drive and more; all just a few blocks from your door. Giant house on 2 levels with over 3,500 square feet of living space and 6 bedrooms. Nicely decorated and lots of places to sit and mingle or watch one of the 85" TVs. Private 2 spot parking in garage and a parking pad for oversized vehicles.

Midcentury Modern Lakeview 2 Bedroom Apartment
Sunny 2 Bedroom, 1 Bath Lakeview Apartment near DePaul, just a short cab from Magnificent Mile, less than 1 mile from Wrigley Field in bustling area with ample entertainment, restaurants, bars & cafes. Walking distance to Chicago Lakefront, Lakeview, Lincoln Park Nearby venues- The Vic, Blueman Group, Wrigley Field, Schubas, Laugh Factory, DePaul, Illinois Masonic, & more.
Popular amenities for lake access rentals in Woodlawn
Lake access house rentals

Spacious Two Story Luxurious Home w/Outdoor Deck!

Uptown Townhouse - Walk to Lake Front and Red Line

B42: Spacious w/ Modern Art/Decor Mins to DWTN

Amazing historic campus mansion!

CasaNova Modern City Living

Historic Old Town, Fabulous 4 Bedroom Home

Private 3rd Floor Apartment

Private Downtown Retreat with Rooftop Oasis
Apartment rentals with lake access

Steps to Mag Mile, 2 BD , fast Wi-Fi, W&D

The Lakefront Lookout (Rooftop Deck • Gym)

Bronzeville Bohemian Loft

Lakeview Charmer -with parking!

cozy grand studio 2nd floor/near lake/public tran.

OLD TOWN TRIUMPHANT 2BD/2BA (+Rooftop&Parking)

Andersonville Living

Luxury Penthouse Loft w/Terrace 507 | River North
Other holiday rentals with lake access

Archways at the Lincoln Park Zoo 2bed/2ba

Elegant Rogers Park Home for 8 guest w/parking

Two Kings Chicago. Royal comfort in two king beds

Spacious Chicago South Side Condo

Inspired Sanctuary, perfect Andersonville location

10-Min Walk to UChicago Medical Center | Quiet 2BR

NEW! |Studio Apartment Whiting IN, United States#2

*New* Luxury Wrigley Penthouse, Free Parking
When is the best time to visit Woodlawn?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $90 SGD | $97 SGD | $116 SGD | $90 SGD | $151 SGD | $153 SGD | $128 SGD | $97 SGD | $70 SGD | $92 SGD | $69 SGD | $79 SGD |
| Avg. temp | -3°C | -1°C | 4°C | 10°C | 16°C | 22°C | 25°C | 24°C | 20°C | 13°C | 6°C | 0°C |
Quick stats about holiday rentals with lake access in Woodlawn

Total holiday rentals
Explore 30 holiday rentals in Woodlawn

Nightly prices starting at
Woodlawn holiday rentals start at $38 SGD per night before taxes and fees

Verified guest reviews
Over 860 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
30 of Woodlawn holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Woodlawn rentals
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- Rentals with lake access Chicago
- Rentals with lake access Cook County
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- Rentals with lake access United States
- Lincoln Park
- Wrigley Field
- Millennium Park
- United Center
- Grant Park
- Navy Pier
- Chicago River Walk
- Soldier Field
- 875 North Michigan Avenue
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- The Field Museum
- Guaranteed Rate Field
- Union Park
- Lincoln Park Zoo
- University of Chicago
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- Museum of Science and Industry
- Washington Park Zoo
- Illinois Beach State Park
- Loyola University Chicago





