Winnetka Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Winnetka holiday rentals

A spacious lobby with a high ceiling, a reception desk, comfortable seating, and a large stained glass window.

1. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (309 reviews)
"The rooms were clean, and the staff was courteous and the Breakfast was excellent."
United States
Ernest
The price is NZ$406
includes taxes & fees
15 Dec - 16 Dec
The Gem Museum Suites
A modern interior with a dining area, seating, a fireplace, and large windows offering a view of buildings outside.

2. 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 NZ$750
includes taxes & fees
16 Nov - 17 Nov
Chicago's Hidden Treasure "Evanston, IL" Urban Luxury with comfort
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 NZ$373
includes taxes & fees
16 Nov - 17 Nov
Spacious 2BR Close to it All - Chic Apt in Skokie
A modern interior with a dining area, seating, a fireplace, and large windows offering a view of buildings outside.

4. 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, (42 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 NZ$665
includes taxes & fees
19 Nov - 20 Nov
Executively Appointed Condo, w/resort amenities, IND GAR, Pool, Gym+ Biz Lounge
An outdoor patio area with a wooden fence, outdoor seating with chairs and a table, and multiple ground lamps.

5. Sunny Work From Home Apt: Near Northwestern-Chicago-Beaches-Loyola

Sunny Work From Home Apt: Near Northwestern-Chicago-Beaches-Loyola
South Evanston
10.0 out of 10, Exceptional, (10 reviews)
"Everything was as described. I would stay here again."
United States
Brent S.
The price is NZ$484
includes taxes & fees
16 Nov - 17 Nov
Sunny Work From Home Apt: Near Northwestern-Chicago-Beaches-Loyola
A dining area with a long table set for four, a chandelier, and a view of the outdoors.

6. Haus Of Hues: MDRN Bright Peaceful Private Apt

Haus Of Hues: MDRN Bright Peaceful Private Apt
South Evanston
9.6 out of 10, Exceptional, (25 reviews)
"This stay was exactly as listed. Very cute apartment and great location!"
United States
Bradie R.
The price is NZ$709
includes taxes & fees
15 Nov - 16 Nov
Haus Of Hues: MDRN Bright Peaceful Private Apt
A patio area with outdoor seating and solar-powered lights.

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

Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
South Evanston
10.0 out of 10, Exceptional, (61 reviews)
"Great apt, excellent host"
United States
Colleen B.
The price is NZ$478
includes taxes & fees
29 Nov - 30 Nov
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
A modern kitchen with white cabinets, a microwave, and a stove. There is a yellow armchair with a white pillow next to a large gray and white flower painting on the wall.

8. Stunning & Stylish Downtown Studio - Highland Park

Stunning & Stylish Downtown Studio - Highland Park
Highland Park
8.4 out of 10, Very good, (7 reviews)
"Great location, quiet area, easy walking into town for breakfast etc"
United States
Tom B.
The price is NZ$278
includes taxes & fees
6 Dec - 7 Dec
Stunning & Stylish Downtown Studio - Highland Park
A two-story brick building with a stone facade, a red awning, and a front door with a decorative glass panel.

9. 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 NZ$714
includes taxes & fees
16 Nov - 17 Nov
MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
A multi-panel cityscape artwork on a wall.

10. 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, (14 reviews)
"Great place overall! The coffee machine on the 3rd floor was great to have. Beds comfortable."
United States
Lisa m.
The price is NZ$750
includes taxes & fees
16 Nov - 17 Nov
Half a mile from everything in the heart of Evanston, Illinois
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

11. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.6 out of 10, Exceptional, (51 reviews)
"The area was nice! Many restaurants and stores are at walking distance Room was very nice and clean"
United States
Francisco
The price is NZ$247
includes taxes & fees
18 Nov - 19 Nov
Wrigleyville Suites
A building with a stone facade and a large window displaying the text 'LAUNDRY MAT'.

12. 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 NZ$135
includes taxes & fees
1 Dec - 2 Dec
King Bed Non-Smoking
A hotel lobby with sofas, a reception desk, a staircase, and a view of the outside.

13. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (93 reviews)
"The bathroom was really clean. The beds were really comfortable"
United States
Jair
The price is NZ$433
includes taxes & fees
2 Dec - 3 Dec
Kasa Lake Shore Chicago
A modern interior with a dining area, seating, a fireplace, and large windows offering a view of buildings outside.

14. "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, (19 reviews)
"Great spot to stay in Evanston, definitely recommend!"
United States
Surath G.
"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
A hotel room with a bed, two pillows, a nightstand with a lamp, and two abstract paintings on the wall.

15. Chic Studio - In Downtown Highland Park, by Metra

Chic Studio - In Downtown Highland Park, by Metra
Highland Park
8.4 out of 10, Very good, (16 reviews)
"I enjoyed my stay at this property. It is in a great location, very unique and super clean! The host is really kind and helpful. "
United States
Deborah
The price is NZ$276
includes taxes & fees
30 Nov - 1 Dec
Chic Studio - In Downtown Highland Park, by Metra
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 NZ$1,069
includes taxes & fees
19 Nov - 20 Nov
Chicago Riverhouse with private fenced in oasis
A modern kitchen with white cabinets, stainless steel appliances, and a tiled backsplash.

17. 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 NZ$237
includes taxes & fees
10 Dec - 11 Dec
Cozy studio in Andersonville Chicago
A multi-story building with a Tudor-style facade, featuring a mix of brick and timber framing.

18. 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, (18 reviews)
"Great location and clean room! Host was very responsive and helpful!"
United States
Andrew O.
The price is NZ$559
includes taxes & fees
16 Nov - 17 Nov
Cozy apartment with AC and WiFi in awesome Chicago
A building with a brick facade and a large glass window. There is a staircase with a black railing leading to the entrance.

19. Chic Urban Retreat Near Wrigley Field w/Parking

Chic Urban Retreat Near Wrigley Field w/Parking
Lakeview
10.0 out of 10, Exceptional, (79 reviews)
"We had a very nice stay, the place was comfortable and clean, beautifully decorated. We only wish we would’ve had more time! And bonus it came with a parking spot. We hope to come back again!"
United States
Rachael
The price is NZ$782
includes taxes & fees
30 Nov - 1 Dec
Chic Urban Retreat Near Wrigley Field w/Parking
A high-rise building with a glass facade, surrounded by other buildings.

20. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,416 reviews)
"Great for extended stays."
United States
Jeff
The price is NZ$405
includes taxes & fees
14 Dec - 15 Dec
Sentral Michigan Avenue
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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Top Winnetka Hotel Reviews

A Hampton Inn hotel with a modern facade, large windows, and a welcoming entrance.
Hampton Inn Chicago-O'Hare International Airport

Hampton Inn Chicago-O'Hare International Airport

Hampton Inn Chicago-O'Hare International Airport
Schiller Park

10/10 Excellent

Hampton inn is always a good choice and the front desk clerk was wonderful. Dependably good choice for hotel.
Australia
Catherine
Reviewed December 21, 2024
Hampton Inn Chicago-O'Hare International Airport

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 favorite 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 depends 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 NZ$246 per night. Entering your travel dates in the search wizard you might find 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.