Winnetka Holiday Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Winnetka holiday rentals

A spacious hotel lobby with a high ceiling, chandeliers, and a bar area.

1. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (305 reviews)
"The rooms were clean, and the staff was courteous and the Breakfast was excellent."
United States
Ernest
The price is AU$310
includes taxes & fees
16 Nov - 17 Nov
The Gem Museum Suites
A patio area with outdoor seating and solar-powered lights.

2. Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More

Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
South Evanston
10.0 out of 10, Exceptional, (60 reviews)
"Great apt, excellent host"
United States
Colleen B.
The price is AU$393
includes taxes & fees
23 Nov - 24 Nov
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
A bedroom with a bed, a ceiling fan, a radiator, a window with blinds, and a potted plant.

3. Spacious 2BR Close to it All - Chic Apt in Skokie

Spacious 2BR Close to it All - Chic Apt in Skokie
West Dempster
9.0 out of 10, Wonderful, (4 reviews)
"Excellent communication with the host. Easy and secure access to the unit. Well furnished and perfect for my trip. So clean! "
United States
Jean W.
The price is AU$318
includes taxes & fees
16 Nov - 17 Nov
Spacious 2BR Close to it All - Chic Apt in Skokie
A modern living room with a sofa, a coffee table, and a TV stand. A kitchen with a microwave, refrigerator, and bar stools is visible in the background.

4. Half a mile from everything in the heart of Evanston, Illinois

Half a mile from everything in the heart of Evanston, Illinois
Downtown Evanston
10.0 out of 10, Exceptional, (13 reviews)
"Great place overall! The coffee machine on the 3rd floor was great to have. Beds comfortable."
United States
Lisa m.
The price is AU$589
includes taxes & fees
22 Nov - 23 Nov
Half a mile from everything in the heart of Evanston, Illinois
A modern interior with a dining area, seating, a fireplace, and large windows offering a view of buildings outside.

5. Executively Appointed Condo, w/resort amenities, IND GAR, Pool, Gym+ Biz Lounge

Executively Appointed Condo, w/resort amenities, IND GAR, Pool, Gym+ Biz Lounge
Downtown Evanston
9.8 out of 10, Exceptional, (41 reviews)
"This is by far the best experience I’ve had with Abnbs! The place was as advertised, the host was very friendly, prompt and accommodating. "
United States
Brian W.
The price is AU$518
includes taxes & fees
9 Nov - 10 Nov
Executively Appointed Condo, w/resort amenities, IND GAR, Pool, Gym+ Biz Lounge
A building with a stone facade and a large window displaying the text 'LAUNDRY MAT'.

6. King Bed Non-Smoking

King Bed Non-Smoking
Chicago
10.0 out of 10, Exceptional, (289 reviews)
"Clean room and friendly staff made it a good stay."
United States
Anonymous traveller
The price is AU$110
includes taxes & fees
1 Dec - 2 Dec
King Bed Non-Smoking
A modern living room with a blue sofa, a round dining table, and a white desk.

7. MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking

MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
South Evanston
9.4 out of 10, Exceptional, (29 reviews)
"Parking was convenient and accommodations were comfortable."
United States
Evan Q.
The price is AU$656
includes taxes & fees
16 Nov - 17 Nov
MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
A rooftop terrace with a brick wall, large windows, and a metal railing.

8. Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Uptown
10.0 out of 10, Exceptional, (60 reviews)
"Clean, efficient, and conveniently located to plenty of transportation and culture."
United States
Michael S.
The price is AU$363
includes taxes & fees
9 Nov - 10 Nov
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
A rooftop terrace with a brick wall, large windows, and a metal railing.

9. Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Uptown
9.2 out of 10, Wonderful, (32 reviews)
"Very nice and clean place in a great location if you are going to Wrigley"
United States
Paul J.
The price is AU$363
includes taxes & fees
9 Nov - 10 Nov
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
A modern interior with a dining area, seating, a fireplace, and large windows offering a view of buildings outside.

10. Chicago's Hidden Treasure "Evanston, IL" Urban Luxury with comfort

Chicago's Hidden Treasure "Evanston, IL" Urban Luxury with comfort
Downtown Evanston
10.0 out of 10, Exceptional, (40 reviews)
"Very nice place to stay with a great location. Thanks!"
United States
Robin M.
The price is AU$606
includes taxes & fees
16 Nov - 17 Nov
Chicago's Hidden Treasure "Evanston, IL" Urban Luxury with comfort
A modern bedroom with a bed, a sofa, and a hanging plant.

11. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (110 reviews)
"Great location for us near the Edgewood neighborhood. Property was very clean, bed comfy, and owner responsive. We’d stay here again!"
United States
Sherry M.
The price is AU$223
includes taxes & fees
3 Dec - 4 Dec
Cozy studio in Andersonville Chicago
A dining area with a wooden table set for four, chairs, a vase with yellow flowers, and a kitchen in the background.

12. Spacious 4BR near Northwestern with King Beds + Crib

Spacious 4BR near Northwestern with King Beds + Crib
Evanston
10.0 out of 10, Exceptional, (6 reviews)
"Spacious home that accommodates all our guests. Very close to Northwestern University so travel was easy! Home was clean and well taken care of. Would definitely recommend to others and would stay agin when I’m in the area."
United States
Melissa C.
The price is AU$1,444
includes taxes & fees
28 Nov - 29 Nov
Spacious 4BR near Northwestern with King Beds + Crib
A modern house with a covered porch, large windows, and a well-maintained garden with various plants and flowers.

13. Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (90 reviews)
"Great spot, safe, clean, and beautiful environment would highly recommend!"
United States
Chris F.
The price is AU$291
includes taxes & fees
10 Nov - 11 Nov
Master qtr close to nature & easy urban facilities
A modern living room with a blue sofa, a patterned rug, and a television.

14. Great Area Logan Square Apt Games Pets - Sleeps 5

Great Area Logan Square Apt Games Pets - Sleeps 5
Avondale
10.0 out of 10, Exceptional, (2 reviews)
"Place was nice and clean. Great communication from the host! Would stay here again!"
United States
Deborah J.
The price is AU$270
includes taxes & fees
9 Nov - 10 Nov
Great Area Logan Square Apt Games Pets - Sleeps 5
A modern interior with a dining area, seating, a fireplace, and large windows offering a view of buildings outside.

15. "Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
Downtown Evanston
10.0 out of 10, Exceptional, (18 reviews)
"Great spot to stay in Evanston, definitely recommend!"
United States
Surath G.
The price is AU$602
includes taxes & fees
18 Nov - 19 Nov
"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
A covered patio with a hammock, a barbecue grill, and a dining area with a table and chairs.

16. Chicago Riverhouse with private fenced in oasis

Chicago Riverhouse with private fenced in oasis
North Park
10.0 out of 10, Exceptional, (45 reviews)
"House was perfect for our needs and all as described per the listing."
United States
Robert S.
The price is AU$822
includes taxes & fees
19 Nov - 20 Nov
Chicago Riverhouse with private fenced in oasis
A compact kitchen with white cabinets, a black stove, a blue countertop, and a white refrigerator.

17. Cozy apartment with AC and WiFi in awesome Chicago

Cozy apartment with AC and WiFi in awesome Chicago
Rogers Park
7.6 out of 10, Good, (17 reviews)
"Great location and clean room! Host was very responsive and helpful!"
United States
Andrew O.
The price is AU$435
includes taxes & fees
9 Nov - 10 Nov
Cozy apartment with AC and WiFi in awesome Chicago
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

18. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.4 out of 10, Exceptional, (49 reviews)
"Clean room"
United States
Michael
The price is AU$251
includes taxes & fees
9 Nov - 10 Nov
Wrigleyville Suites
A living room with a flat-screen TV on a wooden cabinet, a dark sofa, a coffee table, a floor lamp, and a potted plant.

19. 1BR/1BA City Comfort

1BR/1BA City Comfort
Lincoln Square
8.6 out of 10, Excellent, (13 reviews)
"good place to stay clean and comfortable!"
United States
patricia r.
The price is AU$264
includes taxes & fees
23 Nov - 24 Nov
1BR/1BA City Comfort
A desk with a computer monitor, keyboard, mouse, a lamp, a mug, a plant, and a clock.

20. Private Workspace • Sleeps 4 • Modern and Stylish

Private Workspace • Sleeps 4 • Modern and Stylish
Irving Park
10.0 out of 10, Exceptional, (7 reviews)
"We really enjoyed our stay here. The communication was great. Check-in was flawless. We were able to find free parking close by. The listing is accurate, and the location was perfect for our visit to Chicago. We would definitely stay again. Well-equipped kitchen, in-unit laundry, plug strips and extra bedding all were appreciated."
United States
Karin S.
The price is AU$462
includes taxes & fees
21 Nov - 22 Nov
Private Workspace • Sleeps 4 • Modern and Stylish
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.
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Find holiday rentals that suit your style

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Top Winnetka Hotel Reviews

A modern lounge area with leather sofas, a coffee table, and a patterned rug.
Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG
Rosemont

10/10 Excellent

Everything is as it should be
Australia
Kevin
Reviewed July 2, 2025
Holiday Inn Chicago O'Hare – Rosemont by IHG

Find out more about Winnetka

Everything you need to know about Winnetka holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winnetka holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winnetka holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Winnetka holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winnetka. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winnetka holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winnetka holiday rentals we have selected for you start as low as AU$109 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winnetka rentals

At Expedia, we put the best Winnetka holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winnetka rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winnetka holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winnetka. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find holiday rentals in Winnetka?

Yes, there are holiday rentals close to the most popular sights in Winnetka, or you can select a more secluded option if you're looking for a relaxing stay. Winnetka is known for its shopping and forests. Make sure you have time to check out the sporting events and restaurants during your trip.

What are some of the best holiday rentals that Winnetka has to offer?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This holiday home rental outside of Winnetka is located in the city centre, and has a balcony, a BBQ and air conditioning to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What can I see and do in Winnetka?

Lake Michigan and Maple Street Beach are a couple of lovely local spots to get outside and enjoy nature. While in the area, you can also visit popular places such as Wrigley Field and Navy Pier.

What are holiday rentals like in Winnetka?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winnetka. Holiday rentals offer extras like laundry facilities and kitchens so you'll have everything you need. If you're concerned about a clean environment, a holiday rental can provide a sense of safety away from shared hotel lifts and bustling concierge desks while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for a family trip or a small group gathering.