Winnetka Vacation Rentals
Change your mind
Book hotels with free cancellation
Be picky
Search almost a million properties worldwide
Check prices for these dates
In two weeks
In one month
In two months
In three months
Browse Select Winnetka Vacation Homes

Amazing 3-bedroom house with WiFi and AC in awesome Chicago
Amazing 3-bedroom house with WiFi and AC in awesome Chicago

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
7.8 out of 10, Good, (6)
The price is CA $206
CA $338 total
includes taxes & fees
Aug 24 - Aug 25

Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater
Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater
6.0 out of 10, (2)
The price is CA $302
CA $1,372 total
includes taxes & fees
Sep 3 - Sep 4

North Chi Retreat-Near Navel base-Sauna,Pool, Airhokey, grill,King bed,Tikki Bar
North Chi Retreat-Near Navel base-Sauna,Pool, Airhokey, grill,King bed,Tikki Bar
9.6 out of 10, Exceptional, (4)

Rumble In the Jungle Charming 3-bedroom house in nice Addison with AC, WiFi
Rumble In the Jungle Charming 3-bedroom house in nice Addison with AC, WiFi
8.0 out of 10, Very good, (3)
The price is CA $304
CA $620 total
includes taxes & fees
Sep 9 - Sep 10

4BR Retreat w/ Theater, Game Room & Backyard
4BR Retreat w/ Theater, Game Room & Backyard
8.8 out of 10, Excellent, (6)
The price is CA $96
CA $713 total
includes taxes & fees
Aug 26 - Aug 27

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

Great 3 bedroom rental unit near Logan Square
Great 3 bedroom rental unit near Logan Square
9.6 out of 10, Exceptional, (52)
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.
Save an average of 15% on thousands of hotels when you're signed in
Top Winnetka Hotel Reviews

The Whitehall Hotel, BW Premier Collection
10/10 Excellent
Find out more about Winnetka
Find out more about Winnetka
Winnetka Vacation Homes information
Number of reviews | 355 |
---|---|
Accommodation | 679 Vacation Homes |
Lowest Price | CA $96 |
Highest Price | CA $304 |
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Top Vacation Homes in Other Destinations
More Accommodation Types in Winnetka
- Apartments in Winnetka
- Condo Rentals in Winnetka
- Aparthotels in Winnetka
- Motels in Winnetka
- B&B in Winnetka
- Cottages in Winnetka
- Guest Houses in Winnetka
- Hostels in Winnetka
- Villas in Winnetka
- Resorts in Winnetka
- Cabin Rentals in Winnetka
- Houseboats in Winnetka
- Inns in Winnetka
- Residences in Winnetka
- Hotels
All Accommodation Types
Be inspired: Top Vacation Homes destinations in 2025
- Orlando Vacation Homes
- Florida Vacation Homes
- Kissimmee Vacation Homes
- Hawaii Vacation Homes
- Costa Rica Vacation Homes
- Walt Disney World® Vacation Homes
- Palm Springs Vacation Homes
- Naples Vacation Homes
- Victoria Vacation Homes
- Kelowna Vacation Homes
- Toronto Vacation Homes
- Las Vegas Vacation Homes
- Vancouver Vacation Homes
- Mexico Vacation Homes
- Phoenix Vacation Homes
- Fort Lauderdale Vacation Homes
- Davenport Vacation Homes
- Myrtle Beach Vacation Homes
- Los Angeles Vacation Homes
- Cape Coral Vacation Homes
More ways to book
Expedia's Latest Trends
Hotels
- Hotels in Schaumburg
- Hotels in Rosemont
- Hotels near Soldier Field
- Hotels in Naperville
- Hotels near United Center
- Hotels near McCormick Place
- Hotels near Wrigley Field
- Hotels near Lollapalooza
- Hotels in Collingwood
- Hotels near Michigan Avenue
- Hotels near Art Institute of Chicago
- Hotels near Millennium Park
- Hotels near Chicago Riverwalk
- Pickering Casino Resort Hotel
Flights
Activities
Packages