Short-Term Rentals in Woodlawn, IL: Compare 10+ Sites & Save

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725 Best Short-Term Rentals in Woodlawn (Starting from $45)

Woodlawn Oasis
Woodlawn Oasis
House
Chicago, IL, USA
0.3k from Woodlawn center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

3 Bedrooms12 Guests
7.0

Good

2 reviews

$331
Average price / night
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Beautiful newly renovated townhome, very quite, safe, centralized location.\n
Beautiful newly renovated townhome, very quite, safe, centralized location.\n
House
Chicago, IL, 60637, United States
0.2k from Woodlawn center

AC, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
New to Booking
$303
Average price / night
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Kenwood Apartments, Downtown Hyde Park
Kenwood Apartments, Downtown Hyde Park
House
Chicago, IL, USA
0.4k from Woodlawn center

Accommodations, Parking, Homestays, Lodgings, Places to stay

25 Bedrooms75 Guests
6.1

Good

44 reviews

$141
Average price / night
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The MOD Suite: Quaint family abode near UChicago, Lakeshore Dr. & DuSable Museum
The MOD Suite: Quaint family abode near UChicago, Lakeshore Dr. & DuSable Museum
Apartment
Chicago, IL, 60637, United States
0.4k from Woodlawn center

AC, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

3 Bedrooms7 Guests
New to Booking
$146
Average price / night
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Luxe Loft vibe with King Suite - 4BR 3Ba
Luxe Loft vibe with King Suite - 4BR 3Ba
Apartment
Chicago, IL, USA
0.6k from Woodlawn center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay

4 Bedrooms8 Guests
New to Booking
$405
Average price / night
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Chic 3-bedroom well-appointed condo near University of Chicago and Lakeshore
Chic 3-bedroom well-appointed condo near University of Chicago and Lakeshore
Condo
Chicago, IL, 60637, United States
0.4k from Woodlawn center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

3 Bedrooms6 Guests
New to Booking
$212
Average price / night
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The Brown House - A luxurious UChicago Campus stay
The Brown House - A luxurious UChicago Campus stay
Apartment
Chicago, IL, USA
0.9k from Woodlawn center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Family

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$407
Average price / night
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Near Lakefront! Minutes from the beach, Obama museum campus and 2 golf courses!!
Near Lakefront! Minutes from the beach, Obama museum campus and 2 golf courses!!
House
Chicago, IL, 60637, United States
0.5k from Woodlawn center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
9.6

Exceptional

5 reviews

$549
Average price / night
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Parisian Retreat 6min to Main Quandrangle U of C
Parisian Retreat 6min to Main Quandrangle U of C
Apartment
Chicago, IL, USA
1.0k from Woodlawn center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Self-catering

3 Bedrooms6 Guests
9.0

Fabulous

1 reviews

$486
Average price / night
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3BR near U Chicago and Obama Center, Easy Parking
3BR near U Chicago and Obama Center, Easy Parking
Apartment
Chicago, IL, 60637, United States
0.5k from Woodlawn center

AC, Dryer, Heater, Internet, Laundry, Living Area, No Smoking, Washer

3 Bedrooms6 Guests
8.0

Good

1 reviews

$512
Average price / night
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La Casa Negra Chicago A Beautiful 3Bed 2Bath
La Casa Negra Chicago A Beautiful 3Bed 2Bath
Apartment
Chicago, IL, USA
1.3k from Woodlawn center

Apartments, Accommodations, Parking, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$270
Average price / night
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Bright Vintage U of C Center Condo with WiFi, AC in enjoyable Chicago
Bright Vintage U of C Center Condo with WiFi, AC in enjoyable Chicago
Condo
Chicago, IL, 60637, United States
0.6k from Woodlawn center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Laundry, Microwave, No Smoking

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$300
Average price / night
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Eco Stay by UChicago, Lakefront & Hyde Park!
Eco Stay by UChicago, Lakefront & Hyde Park!
Apartment
Chicago, IL, USA
1.5k from Woodlawn center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay, Family, Self-catering

2 Bedrooms5 Guests
8.7

Fabulous

3 reviews

$183
Average price / night
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Luxe Loft vibe –4BR/3BA Apt– King Suite-11 minutes from downtown-Families-Groups
Luxe Loft vibe –4BR/3BA Apt– King Suite-11 minutes from downtown-Families-Groups
Apartment
Chicago, IL, 60637, United States
0.6k from Woodlawn center

AC, Dryer, Elevator, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$568
Average price / night
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2 Mi to South Shore Beach Urban Retreat with Yard
2 Mi to South Shore Beach Urban Retreat with Yard
House
Chicago, IL, USA
1.5k from Woodlawn center

Parking, Accessibility, Internet, Guest Services, Fireplace/Heating, Security/Safety, Child Friendly

3 Bedrooms6 Guests
New to Booking
$200
Average price / night
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Woodlawn Oasis...10 Minutes to Dining & Downtown
Woodlawn Oasis...10 Minutes to Dining & Downtown
House
Chicago, IL, 60637, United States
0.6k from Woodlawn center

AC, Arcade, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

3 Bedrooms12 Guests
9.2

Superb

14 reviews

$555
Average price / night
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Chateau de Woodlawn - Peaceful 3 bedroom apartment.
Chateau de Woodlawn - Peaceful 3 bedroom apartment.
Apartment
Chicago, IL, USA
1.6k from Woodlawn center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Self-catering, Accessible hotels

3 Bedrooms6 Guests
8.2

Very Good

11 reviews

$126
Average price / night
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Book the Great Migration Guest House. Family-sized condo near the Green Line.\n\n
Book the Great Migration Guest House. Family-sized condo near the Green Line.\n\n
Apartment
Chicago, IL, 60637, United States
0.7k from Woodlawn center

AC, Dryer, Heater, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$401
Average price / night
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Chateau de Woodlawn - Room II - Le Parisienne
Chateau de Woodlawn - Room II - Le Parisienne
House
Chicago, IL, USA
1.6k from Woodlawn center

B&bs, Cheap, Accommodations, Parking, Guest houses, Homestays, Lodgings, Places to stay, Self-catering

1 Bedroom2 Guests
8.4

Very Good

16 reviews

$65
Average price / night
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Spacious 3BR on UChicago Campus & Hospitals Free Street Parking
Spacious 3BR on UChicago Campus & Hospitals Free Street Parking
Condo
Chicago, IL, 60637, United States
0.9k from Woodlawn center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms6 Guests
10.0

Exceptional

7 reviews

$835
Average price / night
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Chateau de Woodlawn - Room I - La Tour Eiffel
Chateau de Woodlawn - Room I - La Tour Eiffel
House
Chicago, IL, USA
1.6k from Woodlawn center

B&bs, Cheap, Accommodations, Parking, Guest houses, Homestays, Lodgings, Places to stay, Family

1 Bedroom2 Guests
9.0

Fabulous

10 reviews

$45
Average price / night
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Scott House of Woodlawn - Upper 2 Bdrm unit in Chicago; AC and extras
Scott House of Woodlawn - Upper 2 Bdrm unit in Chicago; AC and extras
House
Chicago, IL, 60637, United States
0.9k from Woodlawn center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, No Smoking

2 Bedrooms6 Guests
New to Booking
$401
Average price / night
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The Jewels, 2 bed/2 bath, UChicago 2mi, Parking, DTWN 15mi
The Jewels, 2 bed/2 bath, UChicago 2mi, Parking, DTWN 15mi
Apartment
Chicago, IL, 60637, United States
0.9k from Woodlawn center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking, TV

2 Bedrooms4 Guests
New to Booking
$103
Average price / night
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Family-friendly, spacious, next to Jackson Park. Free parking.
Family-friendly, spacious, next to Jackson Park. Free parking.
Condo
Chicago, IL, 60637, United States
1.0k from Woodlawn center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms6 Guests
9.4

Superb

3 reviews

$337
Average price / night
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Nice 2bedroom apartment steps away from UofChicago
Nice 2bedroom apartment steps away from UofChicago
Apartment
Chicago, IL, 60637, United States
1.0k from Woodlawn center

Heater, Internet, No Smoking, TV

2 Bedrooms6 Guests
New to Booking
$110
Average price / night
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The Hyde Park Hide-A-Way is ready to welcome you with the comfort of home!
The Hyde Park Hide-A-Way is ready to welcome you with the comfort of home!
Apartment
Chicago, IL, 60637, United States
1.1k from Woodlawn center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms5 Guests
9.6

Exceptional

8 reviews

$268
Average price / night
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High-end 2Bdrm Garden Apt. Where Comfort Meets Style
High-end 2Bdrm Garden Apt. Where Comfort Meets Style
Apartment
Chicago, IL, 60637, United States
1.1k from Woodlawn center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, TV

2 Bedrooms5 Guests
10.0

Exceptional

3 reviews

$270
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Short-Term Rentals in Woodlawn.

Stay Near Woodlawn's Top Attractions

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Woodlawn Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 725 verified short-term rentals in Woodlawn, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Woodlawn vary depending on location, property size, and travel dates. Rates typically start from around $45 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Woodlawn include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Woodlawn, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Woodlawn often include amenities such as Fireplace/Heating, Internet, and Wellness Facilities, providing a comfortable and convenient stay.

Short-term rentals in Woodlawn are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.