Winnetka Vacation Rentals
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Vacation Rentals in Winnetka
AeroStay Retreat – 4BR Home Near O’Hare Airport!
Wood Dale IL
Located in Wood Dale, this vacation home is within a 15-minute drive of Donald E. Stephens Convention Center and Allstate Arena.
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Washer
LUXE 3 BR, 2 BA + Hot Tub
Elmhurst IL
$309 nightly
The price is $330 total per night
$330 total
Dec 15 - Dec 16
Total with taxes and fees
With a stay at this vacation home in Elmhurst, you'll be within a 5-minute drive of Elmhurst Hospital - Main Campus and Oak Brook Golf Course.
Kitchen
Washer
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Maywood IL
$223 nightly
The price is $238 total per night
$238 total
Dec 13 - Dec 14
Total with taxes and fees
With a stay at this vacation home in Maywood, you'll be within a 15-minute drive of United Center and State Street.
Kitchen
Washer
Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces
Chicago IL
With a stay at this vacation home in Chicago (Downtown Chicago), you'll be within a 5-minute walk of Michigan Avenue and State Street.
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Washer
Your Next Vacation Home
Des Plaines IL
$282 nightly
The price is $302 total per night
$302 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
With a stay at this vacation home in Des Plaines (Oakton), you'll be a 3-minute drive from Allstate Arena and 7 minutes from Donald E. Stephens Convention Center.
Kitchen
Washer
The Nicest House on VRBO in Chicago? Perhaps.. Custom Built 5 bdrm in West Town
Chicago IL
With a stay at this vacation home in Chicago (West Town), you'll be within a 5-minute drive of United Center and State Street.
Kitchen
Washer
Family frndly TwnHm by navy base
Waukegan IL
With a stay at this vacation home in Waukegan, you'll be a 2-minute drive from Lake Michigan and 7 minutes from Naval Base Great Lakes.
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Washer
Urban Farmhouse near O’Hare Airport
Des Plaines IL
When you stay at this vacation home in Des Plaines, you'll be on a river, within a 10-minute drive of Allstate Arena and Donald E. Stephens Convention Center.
Kitchen
Washer
Beautiful Updated Home near Great Lakes Naval Base
Waukegan IL
With a stay at this vacation home in Waukegan, you'll be a 3-minute drive from Lake Michigan and 8 minutes from Naval Base Great Lakes.
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Washer
3-bedroom building in lovely Westchester with AC, WiFi. Enjoy your stay
Westchester IL
When you stay at this vacation home in Westchester, you'll be within a 10-minute drive of Oak Brook Golf Course and Loyola University Medical Center.
Kitchen
Washer
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Winnetka Vacation Rentals essential information
Accommodation | 583 Vacation Rentals |
|---|---|
Lowest Price | $238 |
Highest Price | $330 |
Popular accommodation | AeroStay Retreat – 4BR Home Near O’Hare Airport!, LUXE 3 BR, 2 BA + Hot Tub, Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed, Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces, Your Next Vacation Home, The Nicest House on VRBO in Chicago? Perhaps.. Custom Built 5 bdrm in West Town, Family frndly TwnHm by navy base , Urban Farmhouse near O’Hare Airport, Beautiful Updated Home near Great Lakes Naval Base, 3-bedroom building in lovely Westchester with AC, WiFi. Enjoy your stay, Luxury Home Away From Your Home, Cozy 3-bedroom house in family-oriented Melrose Park. |