Forrestville Ave Large Suite 
Best Price Match
8.6 (103 Reviews) Apartment
The entire place is yours • 130 m² size • Free parking
Chicago Grand Boulevard • In Woodlawn · 4.1km to center
Best Price Match 41+ Vacation Rentals Near Woodlawn
NearbyHoliday - Vacation Rentals in Woodlawn
The Penthouse, Lux stay near Downtown, UofC & Lake Best Price Match
9.2 (37 Reviews) Apartment
The entire place is yours • 135 m² size • Kitchen
Best Price Match 
New Luxurious 5BD-2BA Duplex-FREE WINE-2CAR Parking Best Price Match
9.1 (18 Reviews) Apartment
The entire place is yours • 158 m² size • Free on-site parking
Chicago Avalon Park • In Woodlawn · 4.5km to center
Best Price Match 
The Black And White Suite Best Price Match
7.1 (20 Reviews) Holiday_home
The entire place is yours • 223 m² size • Free parking
Chicago Grand Boulevard • In Woodlawn · 4.8km to center
Best Price Match 
BOUTIQUE GARDEN HOUSE CHICAGO 3-STORY sleeps 12 Best Price Match
9.7 (6 Reviews) Holiday_home
The entire place is yours • 139 m² size • Free on-site parking
Chicago Greater Grand Crossing • In Woodlawn · 2.7km to center
Best Price Match 
Beautifully Renovated House 10 mins from Downtown Best Price Match
8.3 (12 Reviews) Holiday_home
The entire place is yours • 297 m² size • Kitchen
Chicago Grand Boulevard • In Woodlawn · 4.8km to center
Best Price Match 
The Brown House - A luxurious UChicago Campus stay Best Price Match
10.0 (5 Reviews) Apartment
The entire place is yours • 139 m² size • Free on-site parking
Best Price Match 
Cozy Woodlawn Retreat 1 Best Price Match
9.8 (4 Reviews) Apartment
The entire place is yours • 111 m² size • Free parking
Best Price Match Luxury Places to Stay in Woodlawn
Over 14+ Luxury Places to Stay in or Near Woodlawn
The Study at the University of Chicago Best Price Match
9.1 (1047 Reviews) Hotel
Private parking • Restaurant • Pet friendly
Best Price Match 
Sophy Hyde Park Best Price Match
9.0 (202 Reviews) Hotel
Private parking • Restaurant • Pet friendly
Best Price Match The Penthouse, Lux stay near Downtown, UofC & Lake Best Price Match
9.2 (37 Reviews) Apartment
The entire place is yours • 135 m² size • Kitchen
Best Price Match 
Chic Euro City Getaway- Close to Downtown Best Price Match
8.4 (29 Reviews) Apartment
The entire place is yours • 111 m² size • Free WiFi
Chicago Grand Boulevard • In Woodlawn · 3.5km to center
Best Price Match BOUTIQUE GARDEN HOUSE CHICAGO 3-STORY sleeps 12 Best Price Match
9.7 (6 Reviews) Holiday_home
The entire place is yours • 139 m² size • Free on-site parking
Chicago Greater Grand Crossing • In Woodlawn · 2.7km to center
Best Price Match Forrestville Ave Large Suite Best Price Match
8.6 (103 Reviews) Apartment
The entire place is yours • 130 m² size • Free parking
Chicago Grand Boulevard • In Woodlawn · 4.1km to center
Best Price Match Beautifully Renovated House 10 mins from Downtown Best Price Match
8.3 (12 Reviews) Holiday_home
The entire place is yours • 297 m² size • Kitchen
Chicago Grand Boulevard • In Woodlawn · 4.8km to center
Best Price Match 
Beautiful Big 3 bedroom Quiet Apt near downtown Best Price Match
8.5 (23 Reviews) Apartment
The entire place is yours • 149 m² size • Free on-site parking
Chicago South Shore • In Woodlawn · 3.1km to center
Best Price Match Pet-Friendly Vacation Rentals in Woodlawn
Over 18+ Pet-Friendly Vacation Rentals in or Near Woodlawn
The Study at the University of Chicago Pets allowed Best Price Match
9.1 (1047 Reviews) Hotel
Private parking • Restaurant • Pet friendly
Best Price Match The Black And White Suite Pets allowed Best Price Match
7.1 (20 Reviews) Holiday_home
The entire place is yours • 223 m² size • Free parking
Chicago Grand Boulevard • In Woodlawn · 4.8km to center
Best Price Match 
Chicago Lakeshore Hotel Pets allowed Best Price Match
6.3 (92 Reviews) Hotel
Free on-site parking • Pet friendly • Free WiFi
Best Price Match 
Greater Grand Crossing/Hyde Park Pets allowed Best Price Match
7.4 (23 Reviews) Apartment
The entire place is yours • 12 m² size • Pet friendly
Chicago Greater Grand Crossing • In Woodlawn · 2.6km to center
Best Price Match 
Modern & Spacious Stay by Northwestern Hospital Bronzeville Pets allowed Best Price Match
9.5 (4 Reviews) Apartment
The entire place is yours • 111 m² size • Free parking
Chicago Grand Boulevard • In Woodlawn · 3.3km to center
Best Price Match 
Luxe Loft vibe with King Suite - 4BR 3Ba Pets allowed Best Price Match
9.7 (7 Reviews) Apartment
The entire place is yours • 232 m² size • Free on-site parking
Best Price Match 
Eco Stay by UChicago, Lakefront & Hyde Park! Pets allowed Best Price Match
9.0 (5 Reviews) Apartment
The entire place is yours • 74 m² size • Free on-site parking
Best Price Match 
Sleek 1-Bedroom Apt in Chicago - East Park Tower 0610 rep Pets allowed Best Price Match
8.8 (6 Reviews) Apartment
The entire place is yours • 58 m² size • Pet friendly
Best Price Match Vacation Rentals in Woodlawn
Over 34+ Vacation Rentals in or Near Woodlawn
Forrestville Ave Large Suite Best Price Match
8.6 (103 Reviews) Apartment
The entire place is yours • 130 m² size • Free parking
Chicago Grand Boulevard • In Woodlawn · 4.1km to center
Best Price Match The Penthouse, Lux stay near Downtown, UofC & Lake Best Price Match
9.2 (37 Reviews) Apartment
The entire place is yours • 135 m² size • Kitchen
Best Price Match New Luxurious 5BD-2BA Duplex-FREE WINE-2CAR Parking Best Price Match
9.1 (18 Reviews) Apartment
The entire place is yours • 158 m² size • Free on-site parking
Chicago Avalon Park • In Woodlawn · 4.5km to center
Best Price Match The Black And White Suite Best Price Match
7.1 (20 Reviews) Holiday_home
The entire place is yours • 223 m² size • Free parking
Chicago Grand Boulevard • In Woodlawn · 4.8km to center
Best Price Match BOUTIQUE GARDEN HOUSE CHICAGO 3-STORY sleeps 12 Best Price Match
9.7 (6 Reviews) Holiday_home
The entire place is yours • 139 m² size • Free on-site parking
Chicago Greater Grand Crossing • In Woodlawn · 2.7km to center
Best Price Match Beautifully Renovated House 10 mins from Downtown Best Price Match
8.3 (12 Reviews) Holiday_home
The entire place is yours • 297 m² size • Kitchen
Chicago Grand Boulevard • In Woodlawn · 4.8km to center
Best Price Match The Brown House - A luxurious UChicago Campus stay Best Price Match
10.0 (5 Reviews) Apartment
The entire place is yours • 139 m² size • Free on-site parking
Best Price Match Cozy Woodlawn Retreat 1 Best Price Match
9.8 (4 Reviews) Apartment
The entire place is yours • 111 m² size • Free parking
Best Price Match Villa Places to Stay in Woodlawn
Over 1+ Villa Places to Stay in or Near Woodlawn
Lakefront Rooftop Parking Best Price Match
7.6 (10 Reviews) Villa
The entire place is yours • 204 m² size • Free on-site parking
Chicago South Shore • In Woodlawn · 3.4km to center
Best Price Match Hotels in Woodlawn
Over 7+ Hotels in or Near Woodlawn
Sophy Hyde Park Best Price Match
9.0 (202 Reviews) Hotel
Private parking • Restaurant • Pet friendly
Best Price Match The Study at the University of Chicago Best Price Match
9.1 (1047 Reviews) Hotel
Private parking • Restaurant • Pet friendly
Best Price Match Chicago Lakeshore Hotel Best Price Match
6.3 (92 Reviews) Hotel
Free on-site parking • Pet friendly • Free WiFi
Best Price Match 
Chateau de Woodlawn - Room III - The Dream Catcher Best Price Match
7.5 (35 Reviews) Guest_house
Free on-site parking • Free WiFi • Family rooms
Best Price Match 
Shared, spacious condo near UChicago and Obama Center Best Price Match
7.4 (8 Reviews) Guest_house
Free on-site parking • Free WiFi • Private bathroom
Best Price Match 
Chateau de Woodlawn - Room II - Le Parisienne Best Price Match
7.7 (22 Reviews) Guest_house
Free on-site parking • Free WiFi • Non-smoking rooms
Best Price Match 
Chateau de Woodlawn - Room I - La Tour Eiffel Best Price Match
9.5 (13 Reviews) Guest_house
Free on-site parking • Shuttle service (free) • Free WiFi
Best Price Match Cheap Places to Stay in Woodlawn
Over 7+ Cheap Places to Stay in or Near Woodlawn
Chateau de Woodlawn - Room III - The Dream Catcher Best Price Match
7.5 (35 Reviews) Guest_house
Free on-site parking • Free WiFi • Family rooms
Best Price Match Chateau de Woodlawn - Room II - Le Parisienne Best Price Match
7.7 (22 Reviews) Guest_house
Free on-site parking • Free WiFi • Non-smoking rooms
Best Price Match Chateau de Woodlawn - Room I - La Tour Eiffel Best Price Match
9.5 (13 Reviews) Guest_house
Free on-site parking • Shuttle service (free) • Free WiFi
Best Price Match Shared, spacious condo near UChicago and Obama Center Best Price Match
7.4 (8 Reviews) Guest_house
Free on-site parking • Free WiFi • Private bathroom
Best Price Match Chicago Lakeshore Hotel Best Price Match
6.3 (92 Reviews) Hotel
Free on-site parking • Pet friendly • Free WiFi
Best Price Match Sophy Hyde Park Best Price Match
9.0 (202 Reviews) Hotel
Private parking • Restaurant • Pet friendly
Best Price Match The Study at the University of Chicago Best Price Match
9.1 (1047 Reviews) Hotel
Private parking • Restaurant • Pet friendly
Best Price Match About Woodlawn Vacation Rentals
Looking for places to stay in Woodlawn? Compare top options in Chicago.
With more than 41 Woodlawn vacation rentals, we can help you find a place to stay. These rentals, including vacation homes, holiday homes, and other short-term private accommodations, offer top-notch amenities with strong value, giving you comfort and luxury at the same time. Get more value and more room when you stay in Woodlawn.
Looking for last-minute deals or the best offers on cottages, condos, private villas, and large vacation homes? NearbyHoliday makes it easy to compare different options with a single click. Looking for a rental by owner with swimming pools, hot tubs, pet-friendly stays, or large-suite comforts? You can compare vacation rentals by owner and other popular Airbnb-style properties in Woodlawn. Prices average US $223 a night.
NearbyHoliday makes it easy and safe to find and compare vacation rentals in Woodlawn, with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Top Stay Categories in Woodlawn
Use These Quick Filters to Find a Vacation Rental in Woodlawn
Browse the most useful filters to narrow down vacation rentals, holiday homes, and other places to stay in Woodlawn.
Pro Tip: Use the quick filters above to compare vacation rentals, holiday homes, hotels, resorts, cabins, villas, and pet-friendly places to stay in Woodlawn. These links help you narrow your search faster, discover short-term rentals with the amenities and pricing that fit your trip, and browse popular stay types before checking availability, last-minute options, and the best deals for your preferred travel style.
Weather in Woodlawn
Average temperatures and rainfall by month range to help plan your stay in Woodlawn.
Mar - May
Avg High17°C / 62°F
Avg Low6°C / 42°F
Rainfall106 mm / 4.2 in
Jun - Aug
Avg High28°C / 83°F
Avg Low18°C / 65°F
Rainfall90 mm / 3.5 in
Sep - Nov
Avg High18°C / 65°F
Avg Low9°C / 48°F
Rainfall70 mm / 2.7 in
Dec - Feb
Avg High3°C / 38°F
Avg Low-5°C / 22°F
Rainfall62 mm / 2.4 in