
Vacation rentals in Winnetka
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Top-rated vacation rentals in Winnetka
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
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Popular amenities for Winnetka vacation rentals
Other great vacation rentals in Winnetka
Superhost

Home in Fox Lake
4.89 out of 5 average rating, 55 reviewsStunning Lake Views, Huge Deck, Water Fun!
KymRating, 5 stars2 months ago
Absolutely Loved our stay!! There aren't enough good things to say about the view, location & beautiful house. So fun! There's a pool table, air hockey & 2 free standing video games. Spent every sunset in the Lakeview room😍 Just gorgeous beyond words! Did i mention the Bald Eagle that hangs out in the tree right outside the Lakeview bedroom? Incredible! the lake doesn't freeze over in one spot in front of the lakeview window, saw all the big birds of prey hunt. It was definitely wildlife at its finest. The owners are Very responsive & told us to be on the look out for the eagle! Fantastic time! Loved Loved Loved it & already reserved for our Wedding weekend❤️
Top guest favorite

Home in Schaumburg
5 out of 5 average rating, 51 reviewsGreat location-King beds-Kids playroom
AdamRating, 5 stars3 weeks ago
Ninna's place was fantastic! It was exactly as described, and the process was proactive. Ninna communicated very well and anticipated questions we may have. We had friends from the area join us for dinner, and Ninna was accommodating of that request. Her place was perfect, with everything we may need during our stay. The kitchen was stocked with all the things we needed, and the coffee nook was a nice touch! The kids enjoyed the little playroom upstairs, and the mattresses were very comfortable.
Superhost

Guest suite in Plainfield
4.86 out of 5 average rating, 78 reviewsRelaxing Suite with Independent Entrance
CindyRating, 5 stars1 week ago
Maria’s place was great! Easy access to the Airbnb & the yard was a bonus for our two dogs. Lots of little touches that made the stay pleasant; coffee, water, snacks were all appreciated. The bed was very comfortable too! I would definitely stay again when in the area.
Guest favorite

Apartment in Albany Park
4.86 out of 5 average rating, 42 reviewsElegant 4Bedroom with Free Parking in Albany Park
MatthewRating, 5 stars2 months ago
Wonderful stay as always, thank you so much!
Superhost

Apartment in Jefferson Park
4.63 out of 5 average rating, 24 reviewsCity Gem: Stylish 3BR for Urban Explorers
AnnikaRating, 5 stars1 month ago
Peaceful, felt like home, very spacious and comfortable
Superhost

Home in Round Lake Beach
4.89 out of 5 average rating, 201 reviewsCorner Lakefront Property
ShannonRating, 5 stars1 month ago
Perfect place to stay for my son's graduation from the Navy Academy. Very flexible to the fact we extended our stay to spend more time with our Sailor.. Felt Right At Home!!! Thank you Jacqueline & Mark.. ;-)
Superhost

Home in Wonder Lake
4.82 out of 5 average rating, 73 reviewsGreat Kayaking, biking, hiking get away
RandallRating, 5 stars4 months ago
Check in was easy, and everything was as described. Julie’s place met our needs for a place to stay while visiting family. Her place is clean and well supplied. Lots of room which we didn’t use all of it. The fenced in area was nice to be able to let our dogs out.
Top guest favorite

Home in Lombard
5 out of 5 average rating, 25 reviewsSpacious Home in Chicago Suburbs
JenniferRating, 5 stars2 weeks ago
It was great! The house was lovely and looked newly renovated. It was much roomier than I expected. The beds were very comfortable.
Quick stats about vacation rentals in Winnetka
Total rentals
10 properties
Nightly prices starting at
$20 before taxes and fees
Total number of reviews
150 reviews
Wifi availability
10 properties include access to wifi
Popular amenities
Self check-in, Gym, and BBQ grill
Local attractions
The Happ Inn Bar & Grill, Spirit Elephant, and Taco Nano!
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- Indiana Dunes National Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Oak Street Beach
- Shedd Aquarium
- Guaranteed Rate Field
- Humboldt Park
- Frank Lloyd Wright Home and Studio
- 875 North Michigan Avenue
- Wilmot Mountain Ski Resort
- Six Flags Great America
- The Field Museum
- Lincoln Park Zoo
- Lincoln Park
- Wicker Park
- Museum of Science and Industry
- Grand Geneva Resort & Spa
- Chicago History Museum
- Willis Tower
- Racine North Beach
- Brookfield Zoo
- Flossmoor Golf Club
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