Vacation rentals in Winnetka

Book unique vacation rentals, houses, and more on Airbnb

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Popular amenities for Winnetka vacation rentals

Stay near Winnetka's top sights

Writers Theatre8 locals recommend
Starbucks8 locals recommend
Historic Wagner Farm5 locals recommend
Glencoe Beach4 locals recommend
Graeter's Ice Cream3 locals recommend
Winnetka3 locals recommend

Other great vacation rentals in Winnetka

Superhost
Home in Fox Lake
4.89 out of 5 average rating, 55 reviews

Stunning 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 reviews

Great location-King beds-Kids playroom

AdamRating, 5 stars2 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 reviews

Relaxing 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 reviews

Elegant 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 reviews

City Gem: Stylish 3BR for Urban Explorers

AnnikaRating, 5 stars1 month ago
Peaceful, felt like home, very spacious and comfortable
Guest favorite
Home in Antioch
4.92 out of 5 average rating, 115 reviews

Entertain on The Chain! water sports and sauna.

JoshuaRating, 5 stars2 weeks ago
Tucked along the quiet northern edge of Antioch, this house doesn’t just offer a place to stay - it gives you something to feel. Vaulted ceilings, custom barnwood beds, and raw concrete countertops set the tone: warm, solid, and built with intent. The private beach isn’t flashy - it’s better. Soft sand, still water, and no reason to rush. Grill outside, gather at the big family-style table, then sweat it all out in the sauna that feels like it was made to erase stress. The beds hit the sweet spot between firm and forgiving. Every corner of the place feels curated without being pretentious. Jewel is just up the road if you need supplies, but you’ll quickly forget the outside world exists. And Waylon? The kind of host you rarely get - quick to respond, genuinely helpful, and fully dialed in without hovering. This isn’t just a weekend rental - it’s the kind of place that makes you rethink how you spend your time off. You’ll leave better than you arrived.
Superhost
Home in Round Lake Beach
4.89 out of 5 average rating, 200 reviews

Corner 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 reviews

Great Kayaking, biking, hiking get away

RandallRating, 5 stars3 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.

Quick stats about vacation rentals in Winnetka

  • Total rentals

    10 properties

  • Nightly prices starting at

    ﺩ.ﺇ73 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!

Destinations to explore

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Winnetka