House holiday rentals in Chicago
Find and book unique houses on Airbnb
Top-rated house rentals in 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 Chicago
House rentals with a pool
Home in Highland Park
2-Acre Highland Park Retreat with Heated Pool ~ 5*
Home in Schaumburg
Schaumburg Woodfield Pool House 4bedroom 2.5bath
Home in Lincoln Park
Luxury Cabin in Lakeview
Home in Glen Ellyn
Glen Ellyn Home
Home in Schaumburg
Paradise 4BR w/ Pool & Games
Home in Chicago
2Bed+2Bath PentHouse in South Loop
Home in Carol Stream
Amazing Summer Pool Awaits You!
Home in Bloomingdale
Whole House in Bloomingdale, IL
Weekly house rentals
Home in North Park
Chicago Riverhouse summer on our patio!
Home in Bolingbrook
The Sunshine Spot
Home in Portage Park
The Evergreen House
Home in Joliet
The Garden House - Murals and more
Home in Lake View
1-bedroom with full kitchen, washer/dryer inside
Home in Chicago
Boho Chic Coach House 30Min to downtown W/ Parking
Home in Berwyn
Retro Modern Bungalow | free parking | fire pit
Home in Lake View
2BD/1 BA with summer patio in quiet Roscoe Village
Private house rentals
Home in Munster
Cozy Farmhouse in Munster
Home in West Rogers Park
Private Condo in Chicago w/ Parking, Near Evanston
Home in Garfield Ridge
Chicago Home by Midway near Downtown Attractions
Home in Logan Square
City Cottage in Logan Square-Avondale
Home in Lincoln Park
Charming 3-BED in Lincoln Park/ Old Town & Parking
Home in Bridgeport
Cozy, Quiet, Riverwalk Sanctuary
Home in Wicker Park
Cozy space in Wicker Park
Home in Wrigleyville
Cubby Blue home - Wrigley ~Free Parking~
Quick stats about house rentals in Chicago
Total rentals
1.8K properties
Rentals with dedicated workspaces
1.2K properties have a dedicated workspace
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
470 properties allow pets
Family-friendly rentals
950 properties are a good fit for families
Total number of reviews
69K reviews
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- South Bend Holiday rentals
- New Buffalo Holiday rentals
- Lighthouse rentals United States
- Townhouse rentals United States
- House rentals United States
- Guest house rentals United States
- Earth house rentals United States
- Rentals with a cinema Chicago
- Rentals with outdoor seating Chicago
- Lakehouse rentals Chicago
- Rentals with an EV charger Chicago
- Loft rentals Chicago
- Rentals with breakfast Chicago
- Rentals with a firepit Chicago
- Family-friendly rentals Chicago
- Rentals with an accessible-height bed Chicago
- Monthly Rentals Chicago
- Fitness-friendly rentals Chicago
- Townhouse rentals Chicago
- Rentals with a balcony Chicago
- Smoking-friendly rentals Chicago
- Hotel rentals Chicago
- Pet-friendly rentals Chicago
- Mansion rentals Chicago
- Rentals with a fireplace Chicago
- Private suite rentals Chicago
- Beachfront rentals Chicago
- Rentals with lake access Chicago
- Rentals with a sauna Chicago
- Rentals with pools Chicago
- Apartment rentals Chicago
- Rentals with a hot tub Chicago
- Waterfront rentals Chicago
- Family-friendly rentals Chicago
- Bed and breakfasts Chicago
- Rentals with a patio Chicago
- Boutique hotel rentals Chicago
- Rentals with a washing machine and dryer Chicago
- Flat rentals Chicago
- Rentals with beach access Chicago
- Townhouse rentals Downtown Chicago
- House rentals Downtown Chicago
- House rentals Milwaukee
- Lakehouse rentals Milwaukee
- Lakehouse rentals Lake Geneva
- House rentals Lake Geneva
- Treehouse rentals Illinois
- Lakehouse rentals Illinois
- Townhouse rentals Illinois
- House rentals Illinois
- Tiny house rentals Illinois
- Guest house rentals Illinois
- Townhouse rentals Cook County
- Guest house rentals Cook County
- 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