Winnetka Vacation Rentals

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Winnetka

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (592)
"Staff is friendly and very helpful!"
The price is P6,360
P9,197 total
includes taxes & fees
Dec 8 - Dec 9
Sentral Michigan Avenue
Sonder Market Hall
Interior

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (208)
"Easiest check in and check out process "
The price is P4,048
P4,752 total
includes taxes & fees
Dec 22 - Dec 23
Sonder Market Hall
Sonder South Wabash
Living area

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (395)
"This property was in a good location - walked to Shedd Aquarium, Soldier Field, and good restaurants on South Michigan. Asked a few questions via text with prompt responses. No complaints with this clean property exactly as advertised."
The price is P7,149
P8,393 total
includes taxes & fees
Dec 19 - Dec 20
Sonder South Wabash
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, (332)
"Had a great stay at Kasa! The place had everything necessary to make ourselves right at home. 10/10 looking forward to coming back in the future! "
Kasa Magnificent Mile Chicago
The Neighborhood Hotel-Little Italy
50-inch Smart TV with satellite channels

The Neighborhood Hotel-Little Italy

3.5 star property
9.6 out of 10, Exceptional, (101)
"Comfortably accommodated all in our party. In suite laundry was very helpful. Kitchen had all supplies needed for our stay. I would highly recommend. "
The Neighborhood Hotel-Little Italy
Level Chicago – Old Town
Front of property - evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (269)
"Beautiful place with amazing amenities. Perfect stay for adults or families alike! Highly recommend!"
The price is P9,861
P12,754 total
includes taxes & fees
Dec 8 - Dec 9
Level Chicago – Old Town
Found Chicago powered by Sonder
Exterior

Found Chicago powered by Sonder

3.5 star property
7.6 out of 10, Good, (176)
"Excellent location, amazing price. No nonsense stay, you only get the basics here but very clean and simple. Pros: no carpet in rooms, no extra frilly pillows or curtains, all surfaces look like they can be easily wiped down and disinfected. You can actually open the windows. Self serve toiletry station. Coded locks instead of keys. Great location close to restaurants and bus stops. THE PRICE!!! Cons: non responsive staff in person and online, sometimes no staff at all. No view, stuffy room...
The price is P6,836
P8,024 total
includes taxes & fees
Dec 26 - Dec 27
Found Chicago powered by Sonder
Sonder The Burnham Apartments
Marina

Sonder The Burnham Apartments

3.5 star property
8.8 out of 10, Excellent, (114)
"Great place to stay, really clean and quiet. Beautiful space to sleep . Great aesthetic!"
The price is P8,072
P9,476 total
includes taxes & fees
Dec 23 - Dec 24
Sonder The Burnham Apartments
Kasa South Loop Chicago
42-inch Smart TV with digital channels, TV, streaming services

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (233)
"This was a great place and deserves the exceptional rating. The first night our oven didn’t work and they had it fixed first thing in the morning! All communication was quick and it had all we needed."
Kasa South Loop Chicago
Sonder Jewelers Row
Free toiletries, hair dryer, towels, soap

Sonder Jewelers Row

3.5 star property
8.2 out of 10, Very Good, (132)
"I so enjoyed staying on jewelers row at the Sonder property In Chicago. It was very close to the places I was visiting so I could walk everywhere. It was noisy because of the L train, yes, but when you’re inside, you Barely hear the train. I felt very safe getting into the building and getting up to my room. It was so well appointed. You thought of everything! I just wish I had longer than three days in Chicago and I hope to come back. I would rent the same apartment again without a doubt!"
The price is P8,188
P9,612 total
includes taxes & fees
Dec 23 - Dec 24
Sonder Jewelers Row
Kasa River North Chicago
Exterior

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (100)
"Had a great time and Kosa was awesome! Staff was excellent and the communication along the way was very organized."
The price is P5,120
P6,010 total
includes taxes & fees
Dec 8 - Dec 9
Kasa River North Chicago
Sonder The Plymouth
City view from property

Sonder The Plymouth

3.5 star property
8.2 out of 10, Very Good, (83)
"Perfect for a girls' weekend get-away. Close to CTA station and walkable to many attractions and restaurants. Comfortable and well-stocked with basic necessaries (dishes, cutlery, glassware). Added plus was the roof top terrace we enjoyed on the unseasonably balmy October evening! Our only complaint was not being able to stay longer. We hope to be back."
The price is P6,486
P7,614 total
includes taxes & fees
Dec 23 - Dec 24
Sonder The Plymouth
Sonder The Opal
Exterior

Sonder The Opal

3.5 star property
8.4 out of 10, Very Good, (25)
"Stayed here twice - great place to stay when visiting. Easily walkable to shops, attractions and dining! "
The price is P7,593
P8,914 total
includes taxes & fees
Dec 11 - Dec 12
Sonder The Opal
Sonder Greektown
40-inch flat-screen TV with digital channels, TV

Sonder Greektown

3.5 star property
9.0 out of 10, Wonderful, (33)
"The place was awesome, they had to kick out the people before me, so getting my room was a little bit late "
The price is P9,525
P11,182 total
includes taxes & fees
Dec 17 - Dec 18
Sonder Greektown
Ground Floor Studios in Chicago by 747 Lofts
Exterior

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
9.8 out of 10, Exceptional, (11)
"Its was in a good location for anyone who has family close by. Bed was wonderful. "
Ground Floor Studios in Chicago by 747 Lofts
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.
Don't see what you're looking for?
See all available properties in Winnetka
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other types of properties in Winnetka you may be interested in

Congress Plaza Hotel
Lobby

Congress Plaza Hotel

3.5 star property
7.8 out of 10, Good, (8312)
"Right out front Millenium park yes! Was it haunted I didn't know!"
The price is P5,904
P6,931 total
includes taxes & fees
Dec 8 - Dec 9
Congress Plaza Hotel
River Hotel
View from property

River Hotel

4.0 star property
8.8 out of 10, Excellent, (3601)
"The Hotel needs to get its iwn parking for sure it never stayed we had to walk 2 blocks that was terrible "
The price is P6,109
P7,171 total
includes taxes & fees
Dec 26 - Dec 27
River Hotel
Club Quarters Hotel, Central Loop, Chicago
Premium bedding, in-room safe, desk, laptop workspace

Club Quarters Hotel, Central Loop, Chicago

4.0 star property
8.6 out of 10, Excellent, (3371)
"It was a great experience "
The price is P5,669
P6,655 total
includes taxes & fees
Dec 26 - Dec 27
Club Quarters Hotel, Central Loop, Chicago
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.

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.

How many vacation rentals are there in Winnetka?

Choose from 3 Expedia vacation rentals in Winnetka for a memorable vacation.

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.