Winnetka Holiday Rentals

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Our top choices for Winnetka holiday rentals

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,147 reviews)
"Clean spacious my go to vacation spot all year around "
United States
xavier
The price is AU$289
includes taxes & fees
25 May - 26 May
Sentral Michigan Avenue

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (745 reviews)
"Our stay was very nice. It was comfortable & clean."
United States
Jill
Kasa Magnificent Mile Chicago

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (472 reviews)
"Very clean and nice place"
United States
Hector
The price is AU$396
includes taxes & fees
26 May - 27 May
Level Chicago – Old Town

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
8.8 out of 10, Excellent, (18 reviews)
"Great location, apt well equipped and host very responsive. Wonderful stay. "
United States
Gina G.
The price is AU$365
includes taxes & fees
26 May - 27 May
Modern Comfort: 1BR Unit w/ Laundry

Modern West Loop Gem-City Views & Prime Location 6

Modern West Loop Gem-City Views & Prime Location 6
Downtown Chicago
10.0 out of 10, Exceptional, (21 reviews)
"Everything was walking distance and had everything needed for a comfortable stay "
United States
Daniel
The price is AU$1,131
includes taxes & fees
13 May - 14 May
Modern West Loop Gem-City Views & Prime Location 6

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)
"Overall just great lovely area and chill place, rooms was great and I love the Roku tvs to sit back In chill!"
United States
Chantrice A.
The price is AU$950
includes taxes & fees
4 May - 5 May
Chic 3bed 2bath Home with free parking close to United Center

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 AU$410
includes taxes & fees
9 May - 10 May
The Oak Park Loft

Sunlit 1BR Apartment | Warm & Welcoming Space

Sunlit 1BR Apartment | Warm & Welcoming Space
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 AU$446
includes taxes & fees
10 May - 11 May
Sunlit 1BR Apartment | Warm & Welcoming Space

Downtown Chicago Stay with Free In & Out Parking 4

Downtown Chicago Stay with Free In & Out Parking 4
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"Our stay was wonderful. The views were fantastic. The apartment was centrally located so we were able to walk to restaurants, museums, and theaters. We bookmarked this location for future stays."
United States
Renae S.
The price is AU$1,572
includes taxes & fees
17 May - 18 May
Downtown Chicago Stay with Free In & Out Parking 4

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 location and the place was immaculate. Host was very nice."
United States
Carl M.
The price is AU$553
includes taxes & fees
4 May - 5 May
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

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 AU$501
includes taxes & fees
4 May - 5 May
First floor of Historic Oak Park Villa, Grge:2Cars

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (191 reviews)
"Having a kitchen is great."
United States
Mark
The price is AU$400
includes taxes & fees
10 May - 11 May
Kasa River North Chicago

LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.8 out of 10, Excellent, (45 reviews)
"Nice overall"
United States
Hell
The price is AU$437
includes taxes & fees
4 May - 5 May
LUXE 3 BR, 2 BA + Hot Tub

Oak Park Victorian by FLW Studio

Oak Park Victorian by FLW Studio
Oak Park
10.0 out of 10, Exceptional, (29 reviews)
"Wonderful place to gather for our annual corporate operations retreat. A great place to disconnect and focus. "
United States
Jennifer A.
The price is AU$692
includes taxes & fees
4 May - 5 May
Oak Park Victorian by FLW Studio

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, (5 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 AU$830
includes taxes & fees
26 May - 27 May
River North Rooftop With In and Out Parking 3

LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
The price is AU$398
includes taxes & fees
7 May - 8 May
LIVN Millennium Park Downtown Chicago 2BR

The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (116 reviews)
"Great well taken care of boutique hotel. Loved the decoration and the quiet area of Evanston. Breakfast was great and a sit down service that was much appreciated."
United States
Michael
The price is AU$202
includes taxes & fees
20 May - 21 May
The Gem Museum Suites

Cozy Train Vibes + Rare Parking x3

Cozy Train Vibes + Rare Parking x3
North Center
10.0 out of 10, Exceptional, (18 reviews)
"Justin was so accommodating. He let us in early as our flight was early. The place was clean , the beds and pillows soooo comfy. The location was perfect for why we were in chicago. Loved our time there "
United States
David C.
The price is AU$760
includes taxes & fees
10 May - 11 May
Cozy Train Vibes + Rare Parking x3

LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"We spent most of this trip discussing our NEXT trip - this stay was one of the simplest, easiest, and most satisfying we've ever experienced with a short-term rental. Hands-down will stay again!Unit incredibly clean, close proximity to the areas we needed to be in, and the host was next-level communicative and kind! Thank you for making it so easy for us!"
United States
Stephanie G.
LIVN West Loop Chicago 2 BR City View

Modern Aesthetic 2BR in Evanston Near the Beach

Modern Aesthetic 2BR in Evanston Near the Beach
South Evanston
8.6 out of 10, Excellent, (27 reviews)
"Amazing location. Completely thrilled with our choice of this beautiful place. Thank you!"
United States
Emily M.
The price is AU$600
includes taxes & fees
22 May - 23 May
Modern Aesthetic 2BR in Evanston Near the Beach
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

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 favourite 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 depend 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 AU$202 per night. Entering your travel dates in the search wizard might find you 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 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?

ENVITAE Hotel, 4BR Luxury Modern Apartments: This holiday home rental outside of Winnetka is located in the city centre, and offers a BBQ, 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 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 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.