Winnetka Vacation Rentals from ￥9,041: Search Short-Term Rentals

Q: What are some of the best vacation rentals in Winnetka?

Riverfront Libertyville Retreat w/ Outdoor Kitchen : You might want to consider this vacation rental near Winnetka, which offers a balcony, a selection of games, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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Vacation Rentals in Winnetka

"Great stay!"

￥36,162 total

includes taxes & fees

Jul 9 - Jul 10

"Hotel was nice"

￥79,768 total

includes taxes & fees

Jul 30 - Jul 31

1 bedroom, individually decorated, individually furnished, desk

"Super cool spot in a great part of the city."

￥28,946 total

includes taxes & fees

Jul 16 - Jul 17

49-inch Smart TV with digital channels, TV, streaming services

"Overall experience was great"

36-inch flat-screen TV with digital channels, TV

"Great place and location. "

￥31,879 total

includes taxes & fees

Jul 24 - Jul 25

2 bedrooms, premium bedding, individually decorated

"Fantastically located snd brilliantly appointed aparthotel. Absolutely perfect for our stay, where we were competing at the HYROX world championships. The room was super spacious and had all amenities you could wish for. "

￥44,692 total

includes taxes & fees

Jul 26 - Jul 27

"We love staying at Sonder properties. The apartment has a full kitchen with everything you need, the shower is so refreshing, and the in-room washer/dryer is super handy when traveling."

￥27,231 total

includes taxes & fees

Jul 10 - Jul 11

"Good people great breakfast "

￥35,127 total

includes taxes & fees

Jul 9 - Jul 10

"Great spot. "

Deluxe Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | City view

"Great stay"

"Great stay, clean room!"

50-inch flat-screen TV with digital channels, TV

"Great location and much larger space than I expected. Great location in the Loop with access to public transit and walkable. "

￥30,655 total

includes taxes & fees

Jul 10 - Jul 11

1 bedroom, individually furnished, desk, iron/ironing board

"Our stay was amazing. "

￥33,336 total

includes taxes & fees

Jul 27 - Jul 28

"Absolutely loved staying here! Would 10/10 recommend this place!"

￥17,907 total

includes taxes & fees

Jul 9 - Jul 10

40-inch flat-screen TV with digital channels, TV

"Great location, easy stay!"

￥37,557 total

includes taxes & fees

Jul 27 - Jul 28

2 bedrooms, desk, iron/ironing board, free WiFi

￥85,168 total

includes taxes & fees

Jul 18 - Jul 19

"Great location, charming building. The photos in the listing are very accurate. Super close to the L and restaurants."

￥29,227 total

includes taxes & fees

Jul 9 - Jul 10

1 bedroom, iron/ironing board, WiFi, bed sheets

￥27,814 total

includes taxes & fees

Jul 15 - Jul 16

"Great property! Would visit again!"

1 bedroom, iron/ironing board, free WiFi, bed sheets

"I thought I was in a $300 night hotel, private, and serene surrounding"

￥26,654 total

includes taxes & fees

Jul 15 - Jul 16

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Find out more about Winnetka

Search for holiday rentals in Winnetka on Expedia! You can easily find your home rentals, villas, holiday apartments in Winnetka using one of the methods below:

View our selection of featured holiday rentals in Winnetka
Use the map to find apartments and other holiday homes in the Winnetka neighbourhood you prefer
Enter your travel dates to view the best deals on holiday rentals in Winnetka while they last

Look no further and take a look at our great range of rental properties in Winnetka!

Recent reviews of Winnetka properties

5/5 Excellent

"Excellent location. Only one block away from the lake as well as from the Michigan avenue (shopping area). Our room was nice and clean. I should not say room, it was like an one bedroom apartment without a kitchen. The management was very nice."

A verified traveler stayed at Hilton Chicago/Magnificent Mile Suites

Posted 11 hours ago

The Whitehall Hotel, BW Premier Collection

5/5 Excellent

"We enjoyed our stay at this hotel. Very convenient location, room was clean little bit outdated but overall perfect. Staff was helpful no housekeeping only if you requested. Breakfast …. typical hotel breakfast nothing fancy but it’s ok. We will stay at this hotel again. "

A verified traveler stayed at The Whitehall Hotel, BW Premier Collection

Posted 19 hours ago

Hotel Felix River North/Magnificent Mile

5/5 Excellent

"Love the location of this property as it is close to the train stations. Rooms were clean and had a nice large fridge to hold waters and leftovers. Really cool that the hotel offers coffee and fresh fruit in the lobby in the mornings. "

A verified traveler stayed at Hotel Felix River North/Magnificent Mile

Posted 22 hours ago

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?

Riverfront Libertyville Retreat w/ Outdoor Kitchen: You might want to consider this vacation rental near Winnetka, which offers a balcony, a selection of games, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Winnetka?

Choose from 3 Expedia vacation rentals in Winnetka for a memorable vacation.

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 Naval Base Great Lakes.

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.

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Winnetka Vacation Rentals

Check prices for these dates

Vacation Rentals in Winnetka

Sentral Michigan Avenue

Level Chicago – Old Town

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Kasa Magnificent Mile Chicago

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

Sonder by Marriott Bonvoy The Burnham Apartments Loop

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

The Gem Museum Suites

The Neighborhood Hotel-Little Italy

Kasa South Loop Chicago

Kasa River North Chicago

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

Sonder by Marriott Bonvoy The Opal Apartments River North

Wrigleyville Suites

Sonder by Marriott Bonvoy Greektown Apartments

Huge Projector and Designated Workspace - Near Wrigley!

Lakeview 2BR Apartment

Clean & Equipped 1BR Apt

Luxurious 3 Bedroom Apartment in Chicago

Cozy studio in Andersonville Chicago

Find out more about Winnetka

Recent reviews of Winnetka properties

Hilton Chicago/Magnificent Mile Suites

citizenM Chicago Downtown

InterContinental Chicago Magnificent Mile by IHG

Freehand Chicago

The Whitehall Hotel, BW Premier Collection

River Hotel

Hotel Felix River North/Magnificent Mile

The Westin Michigan Avenue Chicago

Fairmont Chicago at Millennium Park

Frequently asked questions