House holiday rentals in Woodlawn, Chicago
Find and book unique houses on Airbnb
Top-rated house rentals in Woodlawn, Chicago
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Woodlawn, Chicago
House rentals with a pool
Home in Schaumburg
5.0 out of 5 average rating, 3 reviewsParadise 4BR w/ Pool & Games
21–28 Nov
Home in Chicago
4.86 out of 5 average rating, 37 reviewsLuxury Cabin in Lakeview
7–14 Jul
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
19–26 Nov
Home in Glen Ellyn
4.94 out of 5 average rating, 16 reviewsGlen Ellyn Home
23–30 Jul
Home in Chicago Heights
Olympia field -matteson IL- homewood, park forest
22–29 Jul
Home in Gary
4.82 out of 5 average rating, 213 reviewsOasis , Near Beach, Hard Rock and Dunes
20–27 Nov
Home in Chicago
4.8 out of 5 average rating, 15 reviews2Bed+2Bath PentHouse in South Loop
22–29 Jan
Home in Schererville
5.0 out of 5 average rating, 3 reviewsCozy house in Schererville
5–12 Sep
Weekly house rentals
Home in Chicago
5.0 out of 5 average rating, 15 reviewsCozy Haven
14–21 Sep
Home in Chicago
4.9 out of 5 average rating, 29 reviewsCheerful 3 Bedroom, City Oasis
15–22 Oct
Home in Chicago
4.82 out of 5 average rating, 96 reviewsWoodlawn Oasis: 5-15 Mins from Food, Fun, Dining
28 Jan – 4 Feb
Home in Chicago
4.9 out of 5 average rating, 30 reviewsCheerful 2 Bedroom Residential Home with Finished Basement, full kitchen and Dining Room. 2 Residential Parking passes per 24 hour stay!
18–25 Jun
Home in Chicago
4.95 out of 5 average rating, 19 reviewsSpacius unit in historic gem
6–13 Nov
Home in Chicago
5.0 out of 5 average rating, 13 reviewsModern Family Townhouse
26 Dec – 2 Jan
Home in Chicago
4.88 out of 5 average rating, 42 reviewsCozy Chicago House near Hyde Park!
16–23 Aug
Home in Chicago
5.0 out of 5 average rating, 42 reviewsSpacious 3 Level Home with 5 BDR/3 BA & 2 Kitchens
22–29 Sep
Private house rentals
Home in Munster
4.97 out of 5 average rating, 35 reviewsEntire home: Private, Cozy Oasis in Quiet Locale
30 Dec – 6 Jan
Home in Chicago
5.0 out of 5 average rating, 8 reviewsModern Historic Greystone - Near Lake - Free Prkg
8–15 Nov
Home in Chicago
5.0 out of 5 average rating, 15 reviewsChicago Home by Midway near Downtown Attractions
8–15 Jan
Home in Chicago
4.85 out of 5 average rating, 27 reviewsA Family Rowhouse by UChicago
25 Jun – 2 Jul
Home in Munster
5.0 out of 5 average rating, 14 reviewsCozy Farmhouse in Munster
13–20 Jun
Home in Chicago
4.94 out of 5 average rating, 16 reviewsSpacious 3 bedrooms 5 mins from Lakeshore Drive
23–30 Nov
Home in Chicago
5.0 out of 5 average rating, 48 reviewsCozy, Quiet, Riverwalk Sanctuary
5–12 Jan
Home in Chicago
5.0 out of 5 average rating, 10 reviewsModern retreat near I-94
28 Aug – 4 Sep
Quick stats about house rentals in Woodlawn, Chicago
Total rentals
40 properties
Wifi availability
40 properties include access to wifi
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
1.5K reviews
Nightly prices starting at
€ 19 before taxes and fees
Destinations to explore
- Townhouse rentals United States
- Lighthouse rentals United States
- Earth house rentals United States
- House rentals United States
- Guest house rentals United States
- Guest house rentals Chicago
- Lakehouse rentals Chicago
- Townhouse rentals Chicago
- House rentals Chicago
- Guest house rentals Chicago
- Lakehouse rentals Chicago
- Townhouse rentals Chicago
- House rentals Chicago
- House rentals Downtown Chicago
- House rentals Milwaukee
- Lakehouse rentals Milwaukee
- Lakehouse rentals Illinois
- Treehouse rentals Illinois
- Townhouse rentals Illinois
- Tiny house rentals Illinois
- House rentals Illinois
- Guest house rentals Illinois
- Rentals with a washing machine and dryer Woodlawn
- Pet-friendly rentals Woodlawn
- Flat rentals Woodlawn
- Rentals with a fireplace Woodlawn
- Apartment rentals Woodlawn
- Rentals with a patio Woodlawn
- Monthly Rentals Woodlawn
- Rentals with lake access Woodlawn
- Rentals with outdoor seating Woodlawn
- Family-friendly rentals Woodlawn
- Rentals with beach access Woodlawn
- Family-friendly rentals Woodlawn
- Townhouse rentals Cook County
- House rentals Cook County
- Guest house rentals Cook County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom