Winnetka Vacation Rentals

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Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

Our top choices for Winnetka vacation rentals

Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,178 reviews)
"Everything was great and I’d stay there again!"
United States
Luis E.
The price is ￥31,404
￥41,540 total
includes taxes & fees
Jun 30 - Jul 1
Sentral Michigan Avenue
Full-size fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (484 reviews)
"Staff was amazing and the apartment building was phenomenally clean!"
United States
Seke
The price is ￥47,991
￥60,264 total
includes taxes & fees
Jun 30 - Jul 1
Level Chicago – Old Town
Living area

Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.2 out of 10, Wonderful, (37 reviews)
"Amazing !!!!! Would stay again, clean, beautiful Spot, great area !"
United States
Luka
The price is ￥36,134
￥42,416 total
includes taxes & fees
May 31 - Jun 1
Wrigleyville Suites
Breakfast, lunch and dinner served

The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (130 reviews)
"Perfect place to stay!"
United States
Anton
The price is ￥23,359
￥26,742 total
includes taxes & fees
Jun 29 - Jun 30
The Gem Museum Suites
Studio | Interior

Cabin 105 by 747 Lofts

Cabin 105 by 747 Lofts
2.0 star property
West Town
10.0 out of 10, Exceptional, (1 review)
Cabin 105 by 747 Lofts
Design Apartment, Private Bathroom (The Oak Park Loft) | Exterior

The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (6 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is ￥28,936
￥50,811 total
includes taxes & fees
Jun 22 - Jun 23
The Oak Park Loft
Exclusive Apartment, Private Bathroom, Garden View (1st Floor) | Lounge

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
The price is ￥32,119
￥54,455 total
includes taxes & fees
Jun 23 - Jun 24
Historic Oak Park Home
Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Exterior

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
The price is ￥36,653
￥59,646 total
includes taxes & fees
Jun 22 - Jun 23
Historic Oak Park Residence
Interior

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
The price is ￥20,575
￥50,176 total
includes taxes & fees
Jun 2 - Jun 3
River West, Second Floor Chicago by 747 Lofts
Interior

River West, Third Floor Chicago by 747 Lofts

River West, Third Floor Chicago by 747 Lofts
2.0 star property
West Town
9.0 out of 10, Wonderful, (18 reviews)
"Cvs. Dunkin Donuts. Pizza pie all 1-2 blocks walking distance "
United States
Paul
The price is ￥26,451
￥42,010 total
includes taxes & fees
May 31 - Jun 1
River West, Third Floor Chicago by 747 Lofts
Interior

Chicago Third Floor Studio by 747 Lofts

Chicago Third Floor Studio by 747 Lofts
2.0 star property
West Town
9.8 out of 10, Exceptional, (7 reviews)
"Clean, easy to check in, all the household items you’d expect"
United States
Jason
Chicago Third 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

River Hotel

River Hotel

8/10 Good
"Simple, but quite adequate hotel in ideal location. I love the self check-in/out option, microwave, and refrigerator."
Susan 1-night trip
Posted less than an hour ago
River Hotel

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!

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?

ENVITAE Hotel, 4BR Luxury Modern Apartments: Visitors like this Winnetka vacation home rental. It is located in the city center and offers a barbecue grill, air-conditioning, and laundry facilities to help you feel perfectly comfortable 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 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.