Winnetka Holiday Rentals

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Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

Our top choices for Winnetka holiday rentals

Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,094 reviews)
"Best full kitchen multi-room family lodging"
United States
Lee
The price is HK$857
HK$1,236 total
includes taxes & fees
2 Mar - 3 Mar
Sentral Michigan Avenue
Full-sized fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (433 reviews)
"Clean, nice amenities and great staff."
United States
Sydnee
Level Chicago – Old Town
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (184 reviews)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Interior

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
The price is HK$1,048
HK$2,823 total
includes taxes & fees
1 Mar - 2 Mar
River North Rooftop With In and Out Parking 3
Fridge, microwave, oven, stovetop

Sleek 1BR Apartment w/ In-unit Laundry

Sleek 1BR Apartment w/ In-unit Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."
United States
Anonymous traveller
The price is HK$978
HK$1,886 total
includes taxes & fees
18 Mar - 19 Mar
Sleek 1BR Apartment w/ In-unit Laundry
Exterior

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (9 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
The price is HK$5,466
HK$9,466 total
includes taxes & fees
11 Mar - 12 Mar
Spacious 4BR Central Apartment w/ Skyline Views
2 bedrooms

The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is HK$995
HK$2,007 total
includes taxes & fees
2 Mar - 3 Mar
The Oak Park Loft
Interior

Chic 3bed 2bath Home with free parking close to United Center

Chic 3bed 2bath Home with free parking close to United Center
Oak Park
9.8 out of 10, Exceptional, (18 reviews)
"Plenty of space for my family and loved the onsite free parking, that was helpful because we drove everywhere, just a 30 min drive into the heart of the city"
United States
Jessica T.
The price is HK$1,759
HK$5,300 total
includes taxes & fees
27 Feb - 28 Feb
Chic 3bed 2bath Home with free parking close to United Center
Interior

Stylish Luxe King bed w/Free Parkng near DT Oak Pk

Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Oak Park
9.6 out of 10, Exceptional, (98 reviews)
"Cozy place, host was very helpful and responded quickly to all my concerns. I would definitely stay there again. "
United States
Deborah R.
The price is HK$1,013
HK$2,234 total
includes taxes & fees
3 Mar - 4 Mar
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
TV, offices

Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
The price is HK$884
HK$1,775 total
includes taxes & fees
8 Mar - 9 Mar
Sun-Drenched 1BR Apartment
Desk, iron/ironing board, travel cot, WiFi

Chic Studio in the Heart of the Gold Coast

Chic Studio in the Heart of the Gold Coast
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is HK$884
HK$1,717 total
includes taxes & fees
1 Mar - 2 Mar
Chic Studio in the Heart of the Gold Coast
1 bedroom, iron/ironing board, travel cot, WiFi

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (7 reviews)
"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."
United States
Jeffrey
The price is HK$884
HK$1,814 total
includes taxes & fees
1 Mar - 2 Mar
West Loop Living – Bright 1BR
TV, DVD player, books, video library

First floor of Historic Oak Park Villa, Grge:2Cars

First floor of Historic Oak Park Villa, Grge:2Cars
Oak Park
9.6 out of 10, Exceptional, (26 reviews)
"Very clean, comfortable and nicely located!"
United States
Steve P.
The price is HK$1,198
HK$2,527 total
includes taxes & fees
1 Mar - 2 Mar
First floor of Historic Oak Park Villa, Grge:2Cars
Fridge, microwave, oven, stovetop

Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (73 reviews)
"Glad to have found this gem in Oak Park for a two-night stay with friends. Booking and checking in was easy and seamless. Free street parking was a huge bonus. The space was super cute and comfortable. We enjoyed walking around the neighborhood and getting into the city was super easy (we chose to use Lyft instead of the train, but there are train stations within walking distance. Would definitely book this property again the next time I come to Chicago."
United States
Emily B.
The price is HK$845
HK$2,327 total
includes taxes & fees
3 Mar - 4 Mar
Cozy, Comfortable and Convenient apartment. Close to everything!
Fridge, microwave, oven, stovetop

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Westchester
9.8 out of 10, Exceptional, (20 reviews)
"Great place Great location "
United States
Josh W.
The price is HK$1,240
HK$3,242 total
includes taxes & fees
1 Mar - 2 Mar
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Interior

Oak Park Queen

Oak Park Queen
Oak Park
8.2 out of 10, Very good, (32 reviews)
"The property was very clean and comfortable. Good location. The owner was responsive."
United States
Susan S.
The price is HK$697
HK$1,773 total
includes taxes & fees
3 Mar - 4 Mar
Oak Park Queen
Exterior detail

Oak Park Victorian by FLW Studio

Oak Park Victorian by FLW Studio
Oak Park
10.0 out of 10, Exceptional, (29 reviews)
"Great location and walkable to restaurants. "
United States
Laura B.
The price is HK$1,267
HK$3,885 total
includes taxes & fees
3 Mar - 4 Mar
Oak Park Victorian by FLW Studio
Smart TV

F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC

F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
Barrington
9.8 out of 10, Exceptional, (8 reviews)
"Nice little spot in the NW Suburbs. Great jumping off point for everything further North and points South."
United States
Thomas Z.
The price is HK$774
HK$1,372 total
includes taxes & fees
27 Feb - 28 Feb
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
Exterior detail

Quaint Bungalow, near Great Lakes Naval Base

Quaint Bungalow, near Great Lakes Naval Base
Mundelein
9.8 out of 10, Exceptional, (69 reviews)
"Super cozy!! The neighborhood is so so so lovely! "
United States
Andrea M.
The price is HK$1,056
HK$2,536 total
includes taxes & fees
6 Mar - 7 Mar
Quaint Bungalow, near Great Lakes Naval Base
TV

Top floor of Historic Oak Park Home /2 Car Garage

Top floor of Historic Oak Park Home /2 Car Garage
Oak Park
9.6 out of 10, Exceptional, (23 reviews)
"Our stay was wonderful. The location with parking was perfect."
United States
Joan W.
The price is HK$1,152
HK$2,406 total
includes taxes & fees
2 Mar - 3 Mar
Top floor of Historic Oak Park Home /2 Car Garage
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 Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Good time "
Rudy 2-night trip
Posted 15 hours ago
The Royal Sonesta Chicago Downtown

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
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  • 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 holiday rentals in Winnetka?

Yes, there are holiday rentals in Winnetka close to Chocolate Box, 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?

Wrigley Field/Lakeview -Entire Home- Large Groups!: This holiday home rental outside of Winnetka is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 such as Wrigley Field and Naval Base Great Lakes.

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.