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 Kenwood · 1.4km to center
Best Price Match 38+ Vacation Rentals Near Kenwood
NearbyHoliday - Vacation Rentals in Kenwood
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 
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 Kenwood · 1.8km 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 Kenwood · 2.2km to center
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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 Kenwood · 2.0km to center
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Hamaline Luxury Guest House Best Price Match
8.5 (7 Reviews) Villa
The entire place is yours • 1400 m² size • Free on-site parking
Best Price Match 
Stylish Urban Retreat 3 Bedroom Newly Remodeled Best Price Match
8.3 (32 Reviews) Apartment
The entire place is yours • 111 m² size • Free on-site parking
Chicago Grand Boulevard • In Kenwood · 2.4km 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 Luxury Places to Stay in Kenwood
Over 14+ Luxury Places to Stay in or Near Kenwood
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 Hamaline Luxury Guest House Best Price Match
8.5 (7 Reviews) Villa
The entire place is yours • 1400 m² size • Free on-site parking
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 Kenwood · 2.0km to center
Best Price Match Stylish Urban Retreat 3 Bedroom Newly Remodeled Best Price Match
8.3 (32 Reviews) Apartment
The entire place is yours • 111 m² size • Free on-site parking
Chicago Grand Boulevard • In Kenwood · 2.4km 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 Kenwood · 2.2km 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 Kenwood · 1.4km to center
Best Price Match Pet-Friendly Vacation Rentals in Kenwood
Over 17+ Pet-Friendly Vacation Rentals in or Near Kenwood
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 Kenwood · 1.8km 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 Kenwood · 4.7km to center
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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
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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 Kenwood · 1.0km to center
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 Kenwood
Over 27+ Vacation Rentals in or Near Kenwood
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 Kenwood · 1.4km 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 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 Kenwood · 1.8km 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 Kenwood · 2.2km to center
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 Kenwood · 2.0km to center
Best Price Match Hamaline Luxury Guest House Best Price Match
8.5 (7 Reviews) Villa
The entire place is yours • 1400 m² size • Free on-site parking
Best Price Match Stylish Urban Retreat 3 Bedroom Newly Remodeled Best Price Match
8.3 (32 Reviews) Apartment
The entire place is yours • 111 m² size • Free on-site parking
Chicago Grand Boulevard • In Kenwood · 2.4km 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 Villa Places to Stay in Kenwood
Over 1+ Villa Places to Stay in or Near Kenwood
Hamaline Luxury Guest House Best Price Match
8.5 (7 Reviews) Villa
The entire place is yours • 1400 m² size • Free on-site parking
Best Price Match Hotels in Kenwood
Over 11+ Hotels in or Near Kenwood
Hyatt Place Chicago-South/University Medical Center Best Price Match
8.3 (367 Reviews) Hotel
Breakfast • Shuttle service (free) • 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 Study at the University of Chicago Best Price Match
9.1 (1047 Reviews) Hotel
Private parking • Restaurant • Pet friendly
Best Price Match 
Chicago South Loop Hotel Best Price Match
6.4 (3608 Reviews) Hotel
Free on-site parking • Free WiFi • View
Best Price Match 
McCormick Place Guest House Best Price Match
7.6 (173 Reviews) Guest_house
Free parking • Free WiFi • View
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 
Villa Dubois Guest House Best Price Match
6.7 (227 Reviews) Guest_house
Free parking • Free WiFi • View
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 Cheap Places to Stay in Kenwood
Over 11+ Cheap Places to Stay in or Near Kenwood
Chicago South Loop Hotel Best Price Match
6.4 (3608 Reviews) Hotel
Free on-site parking • Free WiFi • View
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 
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 Villa Dubois Guest House Best Price Match
6.7 (227 Reviews) Guest_house
Free parking • Free WiFi • View
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 McCormick Place Guest House Best Price Match
7.6 (173 Reviews) Guest_house
Free parking • Free WiFi • View
Best Price Match About Kenwood Vacation Rentals
Looking for places to stay in Kenwood? Compare top options in Chicago.
With more than 38 Kenwood 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 Kenwood.
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 Kenwood. Prices average US $206 a night.
NearbyHoliday makes it easy and safe to find and compare vacation rentals in Kenwood, 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 Kenwood
Use These Quick Filters to Find a Vacation Rental in Kenwood
Browse the most useful filters to narrow down vacation rentals, holiday homes, and other places to stay in Kenwood.
Pro Tip: Use the quick filters above to compare vacation rentals, holiday homes, hotels, resorts, cabins, villas, and pet-friendly places to stay in Kenwood. 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 Kenwood
Average temperatures and rainfall by month range to help plan your stay in Kenwood.
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