![](https://a0.muscache.com/im/pictures/de6fe07f-2515-4a23-b929-aad2853c6fa9.jpg)
Holiday rentals in Winnetka
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Winnetka
Guests agree: these stays are highly rated for location, cleanliness and more.
0 of 0 items showing
1 of 3 pages
1 of 3 pages
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Winnetka holiday rentals
Other great holiday rentals in Winnetka
![](https://a0.muscache.com/im/pictures/b9d3f6a1-cc27-44d5-8be2-737a6e08332c.jpg?im_w=720)
Guest favourite
Guest house in Evanston
4.9 out of 5 average rating, 83 reviewsCozy Guesthouse near NU - next to Lee Street Beach
![](https://a0.muscache.com/im/pictures/miso/Hosting-1015566750863466087/original/23cdecc6-e23b-422f-9c47-37ffb25b9a8e.jpeg?im_w=720)
Guest favourite
Home in Northbrook
4.97 out of 5 average rating, 29 reviews*King bed *Outdoor Living *Sought-After Area
![](https://a0.muscache.com/im/pictures/miso/Hosting-741179427015811611/original/cc90dc9e-f364-4d50-bf75-462d28f0ab2a.jpeg?im_w=720)
Guest favourite
Home in Skokie
4.89 out of 5 average rating, 70 reviewsLuxe-Haus of Love—The 1938 Cape Cod |Heated FLRS |
![](https://a0.muscache.com/im/pictures/34535e75-0c81-4fc4-84f3-aa057cea561a.jpg?im_w=720)
Guest favourite
Home in Evanston
4.9 out of 5 average rating, 31 reviewsSleepy sanctuary
![](https://a0.muscache.com/im/pictures/miso/Hosting-51603201/original/6930945c-352d-4dfc-b7f9-5d5652671050.jpeg?im_w=720)
Superhost
Home in Highland Park
5 out of 5 average rating, 26 reviewsSanctuary on the Ravine
![](https://a0.muscache.com/im/pictures/miso/Hosting-38328897/original/86f57b12-384f-4891-9306-583394580d4b.jpeg?im_w=720)
Guest favourite
Apartment in Skokie
4.95 out of 5 average rating, 43 reviewsParking Terrace Near Universities Up to 10%OFF
![](https://a0.muscache.com/im/pictures/hosting/Hosting-1044887929384788288/original/9691f633-e954-49a5-8585-e85622a07be1.jpeg?im_w=720)
Guest favourite
Home in Evanston
5 out of 5 average rating, 23 reviewsWanderlust Cottage
![](https://a0.muscache.com/im/pictures/miso/Hosting-535308409791676515/original/64a94787-6c77-4529-baab-97fb02e54f58.jpeg?im_w=720)
Guest favourite
Home in Highland Park
4.96 out of 5 average rating, 80 reviewsCharming Ranch-Style Cottage
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- South Bend Holiday rentals
- Chicago Holiday rentals
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom