Winnetka Vacation Rentals

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Vacation Rentals in Winnetka

Sentral Michigan Avenue
Indoor pool

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (944)
"Near everything great amenities "
$220 nightly
The price is $258
Oct 5 - Oct 6
Total with taxes and fees
Sentral Michigan Avenue
Kasa Magnificent Mile Chicago
49-inch Smart TV with digital channels, TV, streaming services

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (539)
"Very great place to stay!"
$227 nightly
The price is $266
Oct 6 - Oct 7
Total with taxes and fees
Kasa Magnificent Mile Chicago
Level Chicago – Old Town
Front of property - evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (360)
"Great place to stay. Loved it!"
$252 nightly
The price is $296
Oct 19 - Oct 20
Total with taxes and fees
Level Chicago – Old Town
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
1 bedroom, individually decorated, individually furnished, desk

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.0 out of 10, Very Good, (371)
"Great stay!"
$135 nightly
The price is $159
Oct 19 - Oct 20
Total with taxes and fees
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Lobby

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
8.8 out of 10, Excellent, (235)
"Great location and lovely amenities. "
$186 nightly
The price is $219
Oct 23 - Oct 24
Total with taxes and fees
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Kasa South Loop Chicago
Deluxe Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | Balcony

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (355)
"nice area, shops nearby"
Kasa South Loop Chicago
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
36-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.6 out of 10, Excellent, (669)
"great room, clean good space and close to places "
$169 nightly
The price is $198
Oct 2 - Oct 3
Total with taxes and fees
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
The Neighborhood Hotel-Little Italy
Front of property

The Neighborhood Hotel-Little Italy

4.0 star property
9.6 out of 10, Exceptional, (205)
"This place was perfect "
The Neighborhood Hotel-Little Italy
Sonder by Marriott Bonvoy The Opal Apartments River North
1 bedroom, individually furnished, desk, iron/ironing board

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.4 out of 10, Very Good, (52)
"Place was in a great location close to good restaurants "
$169 nightly
The price is $199
Oct 19 - Oct 20
Total with taxes and fees
Sonder by Marriott Bonvoy The Opal Apartments River North
Kasa River North Chicago
Business center

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (170)
"This place has everything for a multi-night stay."
$291 nightly
The price is $342
Oct 5 - Oct 6
Total with taxes and fees
Kasa River North Chicago
The Gem Museum Suites
Suite, 2 Bedrooms, Kitchen (Three Beds, Washer/Dryer) | Private kitchen | Full-size fridge, microwave, stovetop, dishwasher

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (89)
"Super nice hotel and staff "
$221 nightly
The price is $253
Oct 29 - Oct 30
Total with taxes and fees
The Gem Museum Suites
Wrigleyville Suites
Living area

Wrigleyville Suites

2.0 star property
9.6 out of 10, Exceptional, (19)
"Excellent location and very clean! Would stay again!"
$143 nightly
The price is $159
Oct 2 - Oct 3
Total with taxes and fees
Wrigleyville Suites
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
50-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very Good, (180)
"Great location!!!"
$186 nightly
The price is $219
Oct 22 - Oct 23
Total with taxes and fees
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Stylish Apartment near Chicago Downtown
Classic Apartment | Private kitchen

Stylish Apartment near Chicago Downtown

2.0 star property
$214 nightly
The price is $252
Oct 2 - Oct 3
Total with taxes and fees
Stylish Apartment near Chicago Downtown
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Property amenity

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
7.6 out of 10, Good, (139)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
$209 nightly
The price is $245
Oct 5 - Oct 6
Total with taxes and fees
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Clean & Equipped 1BR Apt
1 bedroom, iron/ironing board, WiFi, bed sheets

Clean & Equipped 1BR Apt

9.4 out of 10, Exceptional, (25)
"Was very clean and comfortable simply furnished but nice close to the things we were looking for. "
$169 nightly
The price is $187
Oct 15 - Oct 16
Total with taxes and fees
Clean & Equipped 1BR Apt
Art Villa
Design Townhome, 3 Bedrooms, Kitchen, City View | Terrace/patio

Art Villa

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
Art Villa
Charming 2BR in Vibrant Lakeview
2 bedrooms, iron/ironing board, travel crib, WiFi

Charming 2BR in Vibrant Lakeview

9.4 out of 10, Exceptional, (19)
"This place was great! Loved my stay!"
$193 nightly
The price is $213
Oct 2 - Oct 3
Total with taxes and fees
Charming 2BR in Vibrant Lakeview
Stylish 1BR in West Loop
Fridge, microwave, oven, stovetop

Stylish 1BR in West Loop

10.0 out of 10, Exceptional, (5)
$195 nightly
The price is $218
Oct 6 - Oct 7
Total with taxes and fees
Stylish 1BR in West Loop
Relaxing Chicago Studio
Desk, iron/ironing board, WiFi, bed sheets

Relaxing Chicago Studio

10.0 out of 10, Exceptional, (15)
"Had a great stay. Great location. "
$130 nightly
The price is $160
Oct 21 - Oct 22
Total with taxes and fees
Relaxing Chicago Studio
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

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"Clean rooms, great staff, everything in walking distance from hotel. Would stay here again. "
Arin 3-night trip
Posted 17 hours ago
Hilton Chicago/Magnificent Mile Suites

Find out more about Winnetka

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 $159 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

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?

2BR Traveler`s Favorite • Modern and Clean: Visitors like this Winnetka vacation home rental. It offers a garden, a barbecue grill, and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

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.