
House vacation rentals in Westchester
Find and book unique houses on Airbnb
Top-rated house rentals in Westchester
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Westchester house rentals
House rentals with a pool

2-Acre Highland Park Retreat with Heated Pool ~ 5*

Comfortable 3BR Home-Prime Video, WiFi, Parking

Spacious 3 Floor Townhome

Now Open: Heated Pool with Entire House

Highwood Haven/Indoor Pool/Hot Tub/Arcade

Paradiso Vacation

Schaumburg Oasis:Private Pool & Enchanted Garden

Beautiful Spanish style Home (w/inground pool)
Weekly house rentals

Casa 22 | Luxury Modern House for 6 | 3 Bed,2 Bath

Bliss in Brookfield- 5BR, 3BA

Guest Favorite Spacious Home Near Chicago O'Hare

Fully Remodeled Large Home

Oak Park - Wine House!

King Bed - Entire Home - Private corner lot

Family Luxury at Brookfield Zoo

RANCH, House-tel: updated full kitchen, comfy beds
Private house rentals

Spacious Designer Oasis: Game Room - Yard - Garage

Executive retreat in Villa Park

Modern Charming Home w/Pergola & games

Lakefront View Getaway Home! Hot tub! Kayak!

Spacious Home in Chicago Suburbs

Large Cottage near Hinsdale Oakbrook sleeps 5

2BDRM Entire Home+Pool Table- 20min to MDW

Cozy 1-Bedroom Apartment on the Ground Floor
Destinations to explore
- Chicago Vacation rentals
- Indianapolis Vacation rentals
- Downtown Chicago Vacation rentals
- Platteville Vacation rentals
- St. Louis Vacation rentals
- Detroit Vacation rentals
- Columbus Vacation rentals
- Louisville Vacation rentals
- Southern Indiana Vacation rentals
- Cincinnati Vacation rentals
- Milwaukee Vacation rentals
- Wisconsin River Vacation rentals
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- Shedd Aquarium
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- The Field Museum
- Illinois Beach State Park
- Wicker Park
- Garfield Park Conservatory
- Brookfield Zoo
- Museum of Science and Industry
- Lincoln Park Zoo
- Willis Tower
- Raging Waves Waterpark
- The 606
- The Beverly Country Club
- Wilmot Mountain Ski Resort