
Apartment holiday rentals in Woodlawn
Find and book unique apartments on Airbnb
Quick stats about apartment rentals in Woodlawn

Total holiday rentals
Explore 40 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 2,340 verified reviews to help you choose

Family-friendly holiday rentals
30 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
40 of Woodlawn holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Woodlawn rentals

4.7 Average rating
Woodlawn stays receive an average rating of 4.7 out of 5 from guests
Top-rated apartment rentals in Woodlawn
Guests agree: these apartments are highly rated for location, cleanliness and more.

Large Remodeled Home in Lincoln Park, Sleeps 12!
Stay in this thoughtfully remodeled home in Lincoln Park. Sleeps 12 w/ complimentary access to 3 parking spots! Enjoy the spacious layout, massive bedrooms, 2 private decks, and front yard w/ a grill. You will be steps from the North & Clybourn Red Line station, Divvy stations, Binny's, Whole Foods, Trader Joe's, Steppenwolf Theatre, so many incredible restaurants! Our home is (conveniently!) located next to train tracks. If you are a light sleeper, this urban location might not be for you.

NEW Rehabbed Sunny top floor Logan Square
Beautiful, newly renovated three bedroom second (top) floor unit with one bathroom in the heart of Logan Square. Located on the Kimball bus line with free in-building laundry available and plenty of FREE street parking. There is a neighborhood mini mart one door down and a Divvy bike rental stand three blocks away. Come stay in Chicago's hottest neighborhood with some of the best dining and bars the city has to offer. *Fan of the hit TV series "The Bear"? Close to Giant, Pizza Lobo & Margies

Apartment in Clarendon Hills.
Newly renovated Suite in multi family home in Clarendon Hills. Main level: fully equipped kitchen/island, dining area, living room & family room with fireplace. Upper level: Bedroom 1 - king size bed, walk in closet, private bathroom/shower. Bedroom 2 - queen bed, closet. Bedroom 3 - size bed, closet. Living room has a pull-out sofa bed. Family room with gas fireplace, access to deck/outdoor area. Easy access to restaurants, shopping (Oak Brook Mall minutes away), Metra, O’Hare.

1 #11 - 2 Bedroom 1 Bath Condo - McCormick Place
Beautiful and newly renovated premium condo located in the heart of Chicago Chinatown with 2 bedroom, 1 bath, a spacious living room and a well appointed kitchen. This condo has 4 beds and can accomodate 6+ guests. Minutes to Downtown, McCormick Place, and popular attractions. Walking distance to public transit, stores, Walgreens, Starbucks, and many great restaurants. We have properties here and in the vicinity that can accommodate groups of 27 or more guests. Contact us for details.

Newly updated 1BD/1B in Old Irving Chicago!
Welcome to your home away from home in the heart of one of Chicago's safest and quietest neighborhoods! This beautifully updated 1 bedroom apartment offers everything you need for a comfortable and convenient stay. It is perfect for couples, solo travelers, and business visitors. Book now for a truly unforgettable experience in the Windy City! - 1 free parking spot - 400 MB Wifi - 2 smart T.V. with access to Netflix, Hulu, Amazon and more! - Desk - Easy app paid laundry in the building.

Int. Designer’s Lakeview Duplex w/private backyard
A front door walkup duplex condo in the heart of Lakeview neighborhood. 2bed/2 bath with private office space. Surrounded by restaurants, bars and shops & just steps from the Wellington brown line train stop. Luxurious amenities such as designer toiletries, cooking oils/spices, cafe du monde coffee and various teas. Walk to nearby Wrigley, Lake, Lincoln Park Zoo or stay here and enjoy the private backyard garden with large lounge area, gas fireplace, grill, and 10 person dining table

Urban Luxury 1BR/2BA Logan Square Condo w/Garage
Luxurious 1BR/2BA garden-level condo in vibrant Logan Square! Comfortably furnished with tons of light and amenities, conveniently located one block from the Logan Square Blue Line Station and located on a quiet street. Steps from all of the hip restaurants and nightlife in Logan Square. Huge back yard and patio with fire pit for guest use. Free on-site garage parking with remote. And, if using public transit, the Logan Square is 8 stops, ~15-20 minutes from the Loop downtown!

Authentic Condo steps from Wrigley Field!
There's no better place to stay if you are visiting Wrigley Field! You can't possibly get any closer to the action with the building being located at Waveland & Clark! Hear the crowd roar from inside the living room! - Recent major renovations! Brand new central heat and air system! Steps from public transportation, Clark Street night life & Wrigley Field. Large balcony in the back & an additional private balcony off the master bedroom den in the front of the building.

Modern stay in lively Wicker Park neighborhood!
Centrally located in Wicker Park, Chicago, our property is steps from public transportation and a 15-minute drive to downtown. Ideal for couples, small families and groups, solo adventurers, or business travelers exploring the vibrant city. Please note: our main street location near a hospital may have some unavoidable city noises. Our unit can house 3-5 guests, please review the sleeping arrangements prior to booking. Travel RN friendly, rate negotiable, PM us for info!

Modern Chicago Movie Themed Apt
Welcome to Chicago at the Movies! An amazing fully updated apartment in the Ukrainian Village neighborhood. This midcentury modern 3 bedroom home is perfect for groups, couples, and families looking for a perfect Chicago vacation. The property is conveniently located on Grand Avenue just minutes by car, bus or train from Downtown and the Lakefront. We are also just a short 5 Minute ride to the United Center for concerts sports and more!

Unit 1, mins to Downtown and United Center
The whole group will enjoy easy access to everything in Unit 1 from this centrally located place. Three stylish bedrooms with private locked doors with keys, if traveling separate. Super updated Kitchen and bathroom. FREE STREET PARKING and ask for availability of 1 car PAY PRIVATE GARAGE PARKING( for convenience), guests has to PAY for the 1 car private garage parking. Sit and enjoy a nice hot coffee in the morning.

Just remodeled apartment close to airport and mall
This is just remodeled first floor 1 bedroom apartment that has everything you need for a comfortable stay. Conveniently located 14 min from O'hare airport and 10 min from Woodfield mall that has to offer variety of stores and huge amount of restaurants. All kitchenware for cooking your meals, board games for fun, pool to relax in summer and some snacks to get most out of your stay here.
Popular amenities for Woodlawn apartment rentals
Weekly apartment rentals

Modern Loft Perfect for Business Travelers

Golden Girls Inspired GetAway!

ChicagoRiver Double Room

Stylish Space 3BR Apt|15 mins DT|Near Expwy

Comfortable room with easy access to Chicago

First floor condo, 2 bedroom, 2 bathroom, balcony.

Long Term Sunny 3Bd/2Ba, Bucktown at the 606 trail

SuperHost with Private bedroom/bath/entry Lakeview
Pet-friendly apartment rentals

Lovely, Pet Friendly Condo w/ King Bed & Parking!

Quiet and Cozy 2 bedroom condo

2 BR condo in the heart of Old Town

Beautiful Condo in North Kenwood with Parking

Spacious Condo Queen bed 8 minutes to O'Hare

Condo in Chicago Bronzeville 9 mins to downtown #1

FreeParking/Laundry/BigSpace!/FamilyFun!/GameRoom!

OakPk/PublicTran/2bd/sleep6/WiFi/Chgo/Lndry/Garage
Apartment rentals with a pool

Just remodeled apartment close to airport and mall

Best view and luxury style, Located in Downtown

Lovely 2 Bed 2 Bathroom!

Iconic Style, Charming Lake View
When is the best time to visit Woodlawn?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $132 SGD | $137 SGD | $151 SGD | $127 SGD | $161 SGD | $164 SGD | $163 SGD | $157 SGD | $152 SGD | $154 SGD | $143 SGD | $137 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 |





