Vacation rentals in Woodlawn, Chicago

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Woodlawn, Chicago

Guests agree: these stays are highly rated for location, cleanliness, and more.

Superhost

Guest suite in Chicago

4.93 out of 5 average rating, 168 reviews

Bike the Lakefront from a Sleek Urban Retreat

Cook in a stainless-steel kitchen with granite countertops, gleaming utensils, and a well-stocked fridge. Black and gray accents and dark woods offset a muted palette at this open-concept home. Thoughtful details include 800-thread-count linens. A retreat designed to evoke relaxation through luxury and elements of the earth. Lush bath linens & robes, luxury body and hair care products, coupled with sleek design creates a spa bathroom retreat you're sure to enjoy. Full granite and stainless steel kitchen, with wine fridge, stocked with morning essentials and Bronzeville BNB staples to ease you into the day's adventure. Relax or be social in the open space living and dining area equipped with Amazon entertainment system and Wi-Fi providing up-to-date weather, sports, news, the latest movies and yes...sometimes...work. Retreat to one of three sleeping accommodations, each drept in 800 thread count, 100% cotton linens. You'll find Bronzeville BNB thoughtful touches around every corner. Enjoy! You'll have access to the full suite including open floor plan living room/dining room/kitchen, spa bathroom, bedroom with walk in closet, hall closet, rear mud room containing washer/dryer, mop/broom, garbage tray, and fire extinguisher. There is concrete patios at the front and the rear entrances also. The backyard, main property deck and garage are restricted areas. The suite is nestled in the historic Bronzeville-Hyde Park neighborhood. Rent a Divvy bike to explore the 18-mile lakefront recreation trail close by. Chicago’s main attractions are a short drive away. The most efficient way to get around the city is UBER offering door-to-door service to all of Chicago's top attractions. Claim your FREE Uber ride (up to $5) gift from the host by signing up using this link: https://www.uber.com/invite/zkyf4 Divvy bike rentals are an awesome way to explore Chicago's 18 mile lakefront trail. The Divvy Explorer Pass includes 24 hours of bike access, with unlimited trips up to 3 hours each for $15/day. Pick up and return bikes at the 575+ Chicago & Evanston Divvy stations. Download the Divvy app for station locations and ride pass purchases. Your safety is important. Please be safe and aware of your surroundings. In any huge city, things can happen. It is suggested to not walk at night, avoid public transportation outside of downtown, and use rideshare transportation apps to avoid exchanging currency.

Dec 25 – Jan 1

€ 167 per night
Guest favorite

Apartment in Chicago

4.92 out of 5 average rating, 166 reviews

Handicap accessible apartment w/Level-2 EV Charger

Just 12.5 miles from downtown in the extremely quiet Chicago neighborhood of Hegewisch. Walking distance to the South Shore train line, which can easily get you to Chicago museums and entertainment, or attractions in NW Indiana. Private parking in back also gives you the option of driving anywhere and then walking directly to your door, and outside cameras are present for security. Banks, restaurants, grocery, convenience, and liquor stores are all 1 block of the apartment for all your needs.

Nov 12 – 19

€ 97 per night
Superhost

Apartment in South Shore

4.83 out of 5 average rating, 12 reviews

Taste the Best of Chicago

Located in prominent and historic community, this stylish apartment is just across the street from the South Shore Cultural Center, 71st Street beach and a private Golf Course, it’s also 3 minutes from Jackson Park Golf Course - Five minutes away from the grounds of the Obama Presidential Center: Steps from the Metra which gets you Downtown in just 12 minutes…where you’ll find the Museum Campus, Soldier Field, Chicago River walk and Navy Pier, the MOST visited attraction in the state of IL.

Jun 5 – 12

€ 166 per night

Popular amenities for Woodlawn, Chicago vacation rentals

Stay near Woodlawn, Chicago's top sights

Daley's Restaurant22 locals recommend
Jackson Park11 locals recommend
ALDI12 locals recommend
Robust Coffee Lounge41 locals recommend
Apostolic Church of God3 locals recommend
Garden of the Phoenix32 locals recommend

Other great vacation rentals in Woodlawn, Chicago

Superhost

Apartment in Woodlawn

4.92 out of 5 average rating, 24 reviews

Comfy Solar & Green 2BR Near Hot Hyde Park!

Aug 20 – 27

€ 156 per night
Guest favorite

Condo in Woodlawn

4.98 out of 5 average rating, 52 reviews

Comfy 2 Bedroom Apartment w/ Office

Aug 23 – 30

€ 148 per night
Superhost

Apartment in Woodlawn

4.93 out of 5 average rating, 85 reviews

Beautiful European Apartment

Oct 29 – Nov 5

€ 197 per night
Superhost

Apartment in Chicago

4.93 out of 5 average rating, 29 reviews

3 BR w Private Parking Minutes from I-90

Aug 12 – 19

€ 161 per night
Guest favorite

Guesthouse in Hyde Park

5.0 out of 5 average rating, 31 reviews

2 br, 2 bt, detached, UChicago Coachman's House

Nov 5 – 12

€ 316 per night
Guest favorite

Apartment in Woodlawn

4.86 out of 5 average rating, 44 reviews

Chateau de Woodlawn Peaceful 3 bedroom apartment.

Jan 6 – 13

€ 144 per night
Superhost

Apartment in Chatham

4.9 out of 5 average rating, 73 reviews

Carol’s Guesthouse: Your Needs Are Covered!

Nov 13 – 20

€ 137 per night
Guest favorite

Home in Chicago

4.92 out of 5 average rating, 84 reviews

Boho Chic Coach House 30Min to downtown W/ Parking

Jun 10 – 17

€ 145 per night
Guest favorite

Condo in Woodlawn

5.0 out of 5 average rating, 13 reviews

University of Chicago Condo-Upgraded and Spacious

Nov 6 – 13

€ 233 per night
Superhost

Guest suite in Bronzeville

4.85 out of 5 average rating, 92 reviews

Bronzeville Guest Suite - 1 Br

Jun 3 – 10

€ 116 per night
Guest favorite

Apartment in Woodlawn

4.9 out of 5 average rating, 10 reviews

Woodlawn~ Entire Luxury Apt

Oct 3 – 10

€ 190 per night
Superhost

Apartment in East Side

4.85 out of 5 average rating, 59 reviews

Lovely 1-BR Apt with full kitchen & living room

Apr 11 – 18

€ 95 per night

Quick stats about vacation rentals in Woodlawn, Chicago

Total rentals

230 properties

Wifi availability

230 properties include access to wifi

Rentals with dedicated workspaces

150 properties have a dedicated workspace

Pet-friendly rentals

40 properties allow pets

Family-friendly rentals

110 properties are a good fit for families

Total number of reviews

5.8K reviews

Destinations to explore

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Chicago
  6. Woodlawn