Winnetka Vacation Rentals

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Check prices for these dates

Tonight
Jun 28 - Jun 29
Tomorrow
Jun 29 - Jun 30
Next weekend
Jul 4 - Jul 6
In two weeks
Jul 11 - Jul 13

Vacation Rentals in Winnetka

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (795)
"Great stay!"
The price is P6,682
P9,504 total
includes taxes & fees
Jul 1 - Jul 2
Sentral Michigan Avenue
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
8.8 out of 10, Excellent, (546)
"Great stay"
The price is P7,861
P9,229 total
includes taxes & fees
Jun 29 - Jun 30
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
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
8.6 out of 10, Excellent, (308)
"Super cool spot in a great part of the city."
The price is P7,861
P9,229 total
includes taxes & fees
Jul 2 - Jul 3
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Level Chicago – Old Town
Front of property - evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (321)
"Hotel was nice"
The price is P20,998
P25,912 total
includes taxes & fees
Jul 3 - Jul 4
Level Chicago – Old Town
Sonder by Marriott Bonvoy The Burnham Apartments Loop
2 bedrooms, premium bedding, individually decorated

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
8.8 out of 10, Excellent, (191)
"Fantastically located snd brilliantly appointed aparthotel. Absolutely perfect for our stay, where we were competing at the HYROX world championships. The room was super spacious and had all amenities you could wish for. "
The price is P12,895
P15,137 total
includes taxes & fees
Jun 29 - Jun 30
Sonder by Marriott Bonvoy The Burnham Apartments Loop
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, (427)
"We had an amazing week staying here. Highly recommend!!"
Kasa Magnificent Mile Chicago
The Gem Museum Suites
Reception

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (69)
"Very clean, the room was very spacious and everyone was very friendly and the complementary breakfast was good. We also like the location. "
The price is P13,193
P15,103 total
includes taxes & fees
Jul 1 - Jul 2
The Gem Museum Suites
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Property amenity

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
8.2 out of 10, Very Good, (108)
"We love staying at Sonder properties. The apartment has a full kitchen with everything you need, the shower is so refreshing, and the in-room washer/dryer is super handy when traveling."
The price is P7,296
P8,565 total
includes taxes & fees
Jun 29 - Jun 30
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
The Neighborhood Hotel-Little Italy
Front of property

The Neighborhood Hotel-Little Italy

4.0 star property
9.8 out of 10, Exceptional, (172)
"Great spot. "
The Neighborhood Hotel-Little Italy
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, (165)
"Great location and much larger space than I expected. Great location in the Loop with access to public transit and walkable. "
The price is P7,861
P9,229 total
includes taxes & fees
Jun 29 - Jun 30
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
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
8.6 out of 10, Excellent, (40)
"Our stay was amazing. "
The price is P7,861
P9,229 total
includes taxes & fees
Jul 1 - Jul 2
Sonder by Marriott Bonvoy The Opal Apartments River North
Kasa South Loop Chicago
City view

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (310)
"Great stay"
Kasa South Loop Chicago
Wrigleyville Suites
Living area

Wrigleyville Suites

2.0 star property
9.0 out of 10, Wonderful, (6)
"Very close to Wrigley Field, easy to get to and easy in and out. Very comfortable. It's a very nice neighborhood. It would be a good place to stay for a group. With that being said, even though we had no issues you still share a bathroom with other guests. That and parking were the only downsides as far as we are concerned."
The price is P6,673
P10,663 total
includes taxes & fees
Jun 29 - Jun 30
Wrigleyville Suites
Kasa River North Chicago
Library

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (152)
"Great stay, clean room!"
Kasa River North Chicago
Sonder by Marriott Bonvoy Greektown Apartments
40-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
9.0 out of 10, Wonderful, (55)
"Great location, easy stay!"
The price is P12,386
P14,540 total
includes taxes & fees
Jun 29 - Jun 30
Sonder by Marriott Bonvoy Greektown Apartments
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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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.