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Our top choices for Winnetka holiday rentals

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 £188
includes taxes & fees
29 Mar - 30 Mar
Sun-Drenched 1BR Apartment

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
9.4 out of 10, Exceptional, (16 reviews)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is £177
includes taxes & fees
30 Mar - 31 Mar
Modern Comfort: 1BR Unit w/ Laundry

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,114 reviews)
"Clean spacious my go to vacation spot all year around "
United States
xavier
The price is £118
includes taxes & fees
1 Apr - 2 Apr
Sentral Michigan Avenue

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (8 reviews)
"Great communication and hosts. Location and unit was perfect."
United States
Greg C.
The price is £204
includes taxes & fees
30 Mar - 31 Mar
West Loop Living – Bright 1BR

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 £333
includes taxes & fees
14 Apr - 15 Apr
River North Rooftop With In and Out Parking 3

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)
"We had a wonderful stay at this Vrbo! The home was spotless, cozy, and exactly as described. The host was friendly, responsive, and made everything easy from check-in to check-out. We would absolutely stay here again. Highly recommend!"
United States
Brianna K.
The price is £165
includes taxes & fees
30 Mar - 31 Mar
Chic Studio in the Heart of the Gold Coast

Modern West Loop Gem-City Views & Prime Location 4

Modern West Loop Gem-City Views & Prime Location 4
Downtown Chicago
10.0 out of 10, Exceptional, (8 reviews)
"Amazing accommodation"
United States
Jiri N.
The price is £490
includes taxes & fees
26 Mar - 27 Mar
Modern West Loop Gem-City Views & Prime Location 4

Premium Urban 4BR - Perfect Mix of Comfort & Location

Premium Urban 4BR - Perfect Mix of Comfort & Location
Near North Side
10.0 out of 10, Exceptional, (1 review)
"Nice place, clean property, great views "
United States
Zach L.
The price is £322
includes taxes & fees
15 Apr - 16 Apr
Premium Urban 4BR - Perfect Mix of Comfort & Location

2-bedroom apartment just 2 minutes drive to Wrigley Field

2-bedroom apartment just 2 minutes drive to Wrigley Field
North Center
9.6 out of 10, Exceptional, (65 reviews)
"Nice property, great location, super helpful host!"
United States
Carin O.
The price is £241
includes taxes & fees
30 Mar - 31 Mar
2-bedroom apartment just 2 minutes drive to Wrigley Field

Cozy & Furnished 2BR Unit

Cozy & Furnished 2BR Unit
Lincoln Square
9.2 out of 10, Wonderful, (17 reviews)
"Very cozy, amenities in great condition."
United States
Kaitlin T.
The price is £162
includes taxes & fees
29 Mar - 30 Mar
Cozy & Furnished 2BR Unit

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 £186
includes taxes & fees
30 Mar - 31 Mar
The Oak Park Loft

Quaint Bungalow, near Great Lakes Naval Base

Quaint Bungalow, near Great Lakes Naval Base
Mundelein
9.8 out of 10, Exceptional, (69 reviews)
"We had a great stay! The area was peaceful and felt safe. "
United States
Yoselin V.
The price is £241
includes taxes & fees
29 Mar - 30 Mar
Quaint Bungalow, near Great Lakes Naval Base

Nice 1BR Spot, Unwind & Relax

Nice 1BR Spot, Unwind & Relax
Lincoln Square
9.8 out of 10, Exceptional, (28 reviews)
"Very clean & cozy! Conveniently located by great shopping & restaurants!"
United States
SHERI C.
The price is £142
includes taxes & fees
13 Apr - 14 Apr
Nice 1BR Spot, Unwind & Relax

Stylish and Roomy 2BR in Chicago

Stylish and Roomy 2BR in Chicago
Edgewater
9.0 out of 10, Wonderful, (14 reviews)
"Clean room, easy, check-in, great location"
United States
brent w.
The price is £162
includes taxes & fees
29 Mar - 30 Mar
Stylish and Roomy 2BR in Chicago

Chic Suite/Mins to L Train /Laundry/Free Parking

Chic Suite/Mins to L Train /Laundry/Free Parking
Oak Park
9.6 out of 10, Exceptional, (60 reviews)
"Comfortable bed, spacious rooms and clean."
United States
Michael W.
The price is £147
includes taxes & fees
30 Mar - 31 Mar
Chic Suite/Mins to L Train /Laundry/Free Parking

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 £177
includes taxes & fees
30 Mar - 31 Mar
Stylish Luxe King bed w/Free Parkng near DT Oak Pk

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (451 reviews)
"Great value, friendly staff"
United States
Marcus
The price is £162
includes taxes & fees
29 Mar - 30 Mar
Level Chicago – Old Town

Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking

Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
Northlake
10.0 out of 10, Exceptional, (7 reviews)
"Had a great experience here, and also close to the airport!"
United States
Yafeat D.
The price is £95
includes taxes & fees
7 Apr - 8 Apr
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking

Just remodeled apartment close to airport and mall

Just remodeled apartment close to airport and mall
Elk Grove Village
10.0 out of 10, Exceptional, (16 reviews)
"Very nice place to stay in secure neighborhood "
United States
Christina F.
The price is £190
includes taxes & fees
29 Mar - 30 Mar
Just remodeled apartment close to airport and mall

Pine Beam Sloth Apartment next to Blue Line

Pine Beam Sloth Apartment next to Blue Line
Irving Park
10.0 out of 10, Exceptional, (6 reviews)
"Beautifully decorated, spotless unit. Conveniently located."
United States
Holly G.
The price is £183
includes taxes & fees
30 Mar - 31 Mar
Pine Beam Sloth Apartment next to Blue Line
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, apart-hotels, 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 favorite 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 depends 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 £101 per night. Entering your travel dates in the search wizard you might find 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?

HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony: This holiday home rental outside of Winnetka is located in the city centre, and has a balcony, an arcade/games room 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.

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.