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Winnetka Vacation Rentals

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Winnetka vacation rentals

Breakfast, lunch and dinner served

1. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (196 reviews)
"Absolutely amazing property."
United States
Nuriye
$164 nightly
The price is $188
Aug 20 - Aug 21
Total with taxes and fees
The Gem Museum Suites
Living area

2. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
8.8 out of 10, Excellent, (47 reviews)
"would not recommend"
United States
heidi
$169 nightly
The price is $198
Aug 11 - Aug 12
Total with taxes and fees
Wrigleyville Suites
Full-size fridge, microwave, oven, stovetop

3. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (515 reviews)
"We only stayed one night but we definitely want to go back and stay at least two nights. It really was beautiful, clean and very secure."
United States
Martha
$288 nightly
The price is $338
Sep 1 - Sep 2
Total with taxes and fees
Level Chicago – Old Town
Lake

4. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
7.6 out of 10, Good, (11 reviews)
"Great location and super clean!"
United States
Erica
$296 nightly
The price is $352
Sep 7 - Sep 8
Total with taxes and fees
Kasa Lake Shore Chicago
Indoor pool

5. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,243 reviews)
"Great property and location."
United States
Michael
$184 nightly
The price is $216
Aug 30 - Aug 31
Total with taxes and fees
Sentral Michigan Avenue
Apartment, Private Bathroom | Lounge

6. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (11 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
$298 nightly
The price is $341
Aug 18 - Aug 19
Total with taxes and fees
At Home in Oak Park
Exclusive Apartment, Private Bathroom, Garden View (1st Floor) | Lounge

7. Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
$307 nightly
The price is $352
Aug 18 - Aug 19
Total with taxes and fees
Historic Oak Park Home
Studio | Exterior

8. River West, Second Floor Chicago by 747 Lofts

River West, Second Floor Chicago by 747 Lofts
2.0 star property
West Town
9.6 out of 10, Exceptional, (4 reviews)
"I need to somewhere to stay for a night in Chicago and found this place. It had a varying level of reviews but found the property more the suitable for what I paid. Easy to follow instructions to get in, clean, and convienent. They even provide ear plugs to drown out the sounds of the city."
United States
Anonymous traveler
$328 nightly
The price is $328
Aug 14 - Aug 15
Total with taxes and fees
River West, Second Floor Chicago by 747 Lofts
House (3 Bedrooms) | Interior

9. Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line
3.0 star property
Forest Park
$444 nightly
The price is $475
Aug 20 - Aug 21
Total with taxes and fees
Classic Forest Park Foursquare < 1 Mi to Blue Line
Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Exterior

10. Historic Oak Park Residence

Historic Oak Park Residence
2.0 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"The house is in an amazing neighborhood, easy access to subway, extremely clean and great follow-up and follow through communication with owner!"
United States
Ann-Marie
Historic Oak Park Residence
Studio | Living area

11. Ground Floor Studios in Chicago by 747 Lofts

Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
West Town
8.6 out of 10, Excellent, (25 reviews)
"It’s a really nice place. Its quite a distance from downtown Chicago. But it’s like 3 minutes from Chicago Blue line and a minute away from the bus station. Food is not a problem since there is a Korean grocery nearby. There is also a nearby Catholic church. The ameneties in this loft hotel is complete so if you are looking for a budget style trip and accommodation, I highly recommend this place."
United States
Joel
$251 nightly
The price is $251
Aug 12 - Aug 13
Total with taxes and fees
Ground Floor Studios in Chicago by 747 Lofts
Studio | Living area

12. Chicago Second Floor Studio by 747 Lofts

Chicago Second Floor Studio by 747 Lofts
2.0 star property
West Town
9.0 out of 10, Wonderful, (15 reviews)
"i loved this place! would definitely come again"
United States
adrian
$152 nightly
The price is $152
Aug 12 - Aug 13
Total with taxes and fees
Chicago Second Floor Studio by 747 Lofts
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

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

8/10 Good
"Some of the rooms have a view of a brick wall."
Diane 1-night trip
Posted less than an hour ago
The Allegro Royal Sonesta Hotel Chicago Loop

Find out more about Winnetka

Everything you need to know about Winnetka vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winnetka vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winnetka vacation 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 low season months. For more hustle and bustle, you may prefer to visit Winnetka in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $167 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winnetka rentals

At Expedia, we put the best Winnetka vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Winnetka?

Yes, we offer vacation rentals in Winnetka near Chocolate Box, or you can go with a more remote option if you'd like a relaxing place to 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 vacation rentals in Winnetka?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: Visitors like this Winnetka vacation home rental. It is located in the city center and has a balcony, a barbecue grill, 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 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 enjoy the outdoors, whereas family-friendly attractions include Chocolate Box. While in the area, you can also visit popular places like Wrigley Field and United Center.

What are vacation rentals like in Winnetka?

Vacation rentals are private accommodations you can stay in for a couple days or more in Winnetka. Vacation rentals feature extras such as hot tubs, fire pits, and patios so your stay will be comfortable. If you're concerned about cleanliness, a vacation rental can provide a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for family trips.