Winnetka Vacation Rentals

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Jan 8 - Jan 9
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This weekend
Jan 9 - Jan 11
Next weekend
Jan 16 - Jan 18

Our top choices for Winnetka vacation rentals

Exterior
Chicago luxury home suites

Aparthotel in Downtown Chicago

Chicago luxury home suites
2.0 star property
10.0 out of 10, Exceptional, (4)
"Amazing stay! The location is very central and close to everything. The room was spotless, and the mattress was very comfortable. I really appreciated that the property is pet friendly. I was able to bring my dog along, which made the trip even better. The view was absolutely stunning. The hosts were very responsive and helpful throughout our stay. Highly recommend!"
Canada
Alex
$105 nightly
The price is $124
Jan 26 - Jan 27
Total with taxes and fees
Chicago luxury home suites
Indoor pool
Sentral Michigan Avenue

Aparthotel in Downtown Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (1037)
"Place was very nice and clean. We enjoyed the stay there. Will book it again when we come back to Chicago visit again. "
United States
Khalid
$135 nightly
The price is $158
Jan 11 - Jan 12
Total with taxes and fees
Sentral Michigan Avenue
Desk, iron/ironing board, travel crib, WiFi
Gold Coast Living: Modern Studio Unit

Apartment in Downtown Chicago

Gold Coast Living: Modern Studio Unit
10.0 out of 10, Exceptional, (5)
"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
$149 nightly
The price is $166
Jan 11 - Jan 12
Total with taxes and fees
Gold Coast Living: Modern Studio Unit
1 bedroom, WiFi, bed sheets
1BR Modern Luxe Apt with In-Unit Laundry

Apartment in Downtown Chicago

1BR Modern Luxe Apt with In-Unit Laundry
10.0 out of 10, Exceptional, (1)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
$153 nightly
The price is $168
Jan 12 - Jan 13
Total with taxes and fees
1BR Modern Luxe Apt with In-Unit Laundry
1 bedroom, iron/ironing board, travel crib, WiFi
West Loop Living – Bright 1BR

Apartment in Downtown Chicago

West Loop Living – Bright 1BR
10.0 out of 10, Exceptional, (6)
"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."
United States
Jeffrey
$153 nightly
The price is $168
Jan 11 - Jan 12
Total with taxes and fees
West Loop Living – Bright 1BR
Interior
Twice as Nice: Chic 2BR Stay with Style & Space

Apartment in Downtown Chicago

Twice as Nice: Chic 2BR Stay with Style & Space
9.6 out of 10, Exceptional, (19)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
$174 nightly
The price is $191
Jan 11 - Jan 12
Total with taxes and fees
Twice as Nice: Chic 2BR Stay with Style & Space
TV, offices
Modern Comfort: 1BR Unit w/ Laundry

Apartment in Downtown Chicago

Modern Comfort: 1BR Unit w/ Laundry
9.8 out of 10, Exceptional, (11)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
$153 nightly
The price is $168
Jan 11 - Jan 12
Total with taxes and fees
Modern Comfort: 1BR Unit w/ Laundry
TV, offices
Sun-Drenched 1BR Apartment

Apartment in Downtown Chicago

Sun-Drenched 1BR Apartment
10.0 out of 10, Exceptional, (2)
"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.
$153 nightly
The price is $168
Jan 11 - Jan 12
Total with taxes and fees
Sun-Drenched 1BR Apartment
Interior
River North Rooftop With In and Out Parking 3

Apartment in Downtown Chicago

River North Rooftop With In and Out Parking 3
9.6 out of 10, Exceptional, (4)
"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.
$282 nightly
The price is $313
Jan 13 - Jan 14
Total with taxes and fees
River North Rooftop With In and Out Parking 3
TV, offices
The One: A 1BR Stay That Feels Like Home

Apartment in Downtown Chicago

The One: A 1BR Stay That Feels Like Home
8.4 out of 10, Very Good, (5)
"Very nice condo in a quiet neighborhood"
Canada
Patrick
$153 nightly
The price is $168
Jan 15 - Jan 16
Total with taxes and fees
The One: A 1BR Stay That Feels Like Home
TV, offices
Chicago-Themed 1BR in a Central Spot near Downtown

Apartment in Downtown Chicago

Chicago-Themed 1BR in a Central Spot near Downtown
2.0 star property
$153 nightly
The price is $168
Jan 13 - Jan 14
Total with taxes and fees
Chicago-Themed 1BR in a Central Spot near Downtown
Lounge
Kasa River North Chicago

Aparthotel in Downtown Chicago

Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (182)
"Awesome stay "
United States
Sally
$218 nightly
The price is $256
Jan 11 - Jan 12
Total with taxes and fees
Kasa River North Chicago
Full-size fridge, microwave, oven, stovetop
Level Chicago – Old Town

Aparthotel in Downtown Chicago

Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (408)
"Great location, clean room and friendly staff!"
United States
Scott
$195 nightly
The price is $228
Jan 11 - Jan 12
Total with taxes and fees
Level Chicago – Old Town
Fridge, microwave, oven, stovetop
Sleek 1BR Apt w/ Laundry

Apartment in Downtown Chicago

Sleek 1BR Apt w/ Laundry
10.0 out of 10, Exceptional, (1)
"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 traveler
$153 nightly
The price is $168
Jan 21 - Jan 22
Total with taxes and fees
Sleek 1BR Apt w/ Laundry
TV, offices
Complete 1BR Home Sum

Apartment in Downtown Chicago

Complete 1BR Home Sum
$153 nightly
The price is $168
Jan 11 - Jan 12
Total with taxes and fees
Complete 1BR Home Sum
Interior
Stylish Japanese-Themed 2BR Apt Close to Downtown

Apartment in Downtown Chicago

Stylish Japanese-Themed 2BR Apt Close to Downtown
2.0 star property
$176 nightly
The price is $193
Jan 19 - Jan 20
Total with taxes and fees
Stylish Japanese-Themed 2BR Apt Close to Downtown
Terrace/patio
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Apartment in Uptown

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
10.0 out of 10, Exceptional, (49)
"Clean and quiet, perfect for nights to rest after exploring the city"
United States
Joe T.
$203 nightly
The price is $244
Jan 12 - Jan 13
Total with taxes and fees
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Interior
Spacious 3-bedroom apartment near downtown, FREE PARKING

Apartment in Near West Side

Spacious 3-bedroom apartment near downtown, FREE PARKING
9.4 out of 10, Exceptional, (10)
"Great place to stay that was close to downtown"
United States
Michelle B.
$269 nightly
The price is $332
Jan 20 - Jan 21
Total with taxes and fees
Spacious 3-bedroom apartment near downtown, FREE PARKING
Terrace/patio
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

Apartment in Uptown

Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
9.0 out of 10, Wonderful, (19)
"Had a great stay! Perfect for our needs. Great location. It was an easy walk to the lake and lots of great restaurants nearby!"
United States
Rodney S.
$207 nightly
The price is $249
Jan 11 - Jan 12
Total with taxes and fees
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Interior
Pine Beam Sloth Apartment next to Blue Line

Apartment in Irving Park

Pine Beam Sloth Apartment next to Blue Line
2.0 star property
10.0 out of 10, Exceptional, (4)
"Amazing stay! So comfortable, clean, and the sushi underneath was the icing on the cake! We will definitely stay again when we come back! "
United States
Emily s.
$204 nightly
The price is $208
Jan 13 - Jan 14
Total with taxes and fees
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

Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"Beautiful "
Danny 3-night trip
Posted 16 hours ago
Hyatt Regency Chicago

Find out more about Winnetka

Everything you need to know about Winnetka vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winnetka vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winnetka vacation 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 low season months. For more hustle and bustle, you may prefer to visit Winnetka in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $124 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winnetka rentals

At Expedia, we put the best Winnetka vacation 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 vacation.

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.

Explore a world of travel with Expedia

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?

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed: Visitors like this Winnetka vacation home rental. It offers a patio, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave.

What can I see and do in Winnetka?

Lake Michigan and Elder Lane 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.