Winnetka Vacation Rentals

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Check prices for these dates

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Aug 20 - Aug 21
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Vacation Rentals in Winnetka

Our top choices for Winnetka vacation rentals

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (886)
"great food spots all around and beautiful sites to see "
The price is P8,185
P11,282 total
includes taxes & fees
Sep 3 - Sep 4
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
9.4 out of 10, Exceptional, (476)
"It was a great property to stay at, definitely would book again! "
Kasa Magnificent Mile Chicago
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
8.2 out of 10, Very Good, (344)
"Great stay!"
The price is P6,732
P7,903 total
includes taxes & fees
Sep 3 - Sep 4
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, (341)
"A lot of good food options walkable distance. "
Level Chicago – Old Town
The Neighborhood Hotel-Little Italy
Front of property

The Neighborhood Hotel-Little Italy

4.0 star property
9.6 out of 10, Exceptional, (191)
"Property was extremely comfortable in a great area."
The Neighborhood Hotel-Little Italy
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, (622)
"Nice view, and walkable area."
The price is P6,248
P7,335 total
includes taxes & fees
Sep 3 - Sep 4
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Lobby

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
9.0 out of 10, Wonderful, (207)
"Great location, room was very nice. Vent in the bathroom wasn’t working and the walls are paper thin so you can hear other people talking loud. Otherwise a great stay! "
The price is P8,490
P9,967 total
includes taxes & fees
Aug 24 - Aug 25
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Kasa South Loop Chicago
Balcony

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (330)
"Great stay"
Kasa South Loop Chicago
The Gem Museum Suites
Private kitchen

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (83)
"Super nice hotel and staff "
The price is P11,539
P13,210 total
includes taxes & fees
Sep 2 - Sep 3
The Gem Museum 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, (176)
"Great location!!!"
The price is P7,701
P9,040 total
includes taxes & fees
Sep 3 - Sep 4
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Wrigleyville Suites
Living area

Wrigleyville Suites

2.0 star property
9.4 out of 10, Exceptional, (15)
"Excellent location and very clean! Would stay again!"
The price is P8,584
P12,933 total
includes taxes & fees
Aug 22 - Aug 23
Wrigleyville Suites
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, (47)
"Great location. Apartment had all the amenities needed. Felt safe. Only not so good part was that being in downtown, it wasn't super quiet at times. Would stay here again without a doubt."
The price is P7,217
P8,472 total
includes taxes & fees
Sep 3 - Sep 4
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, (163)
"Great location and very clean! Will definitely be staying again. "
Kasa River North Chicago
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Property amenity

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
7.8 out of 10, Good, (131)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
The price is P8,428
P9,893 total
includes taxes & fees
Sep 17 - Sep 18
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Art Villa
Full-size fridge, microwave, oven, stovetop

Art Villa

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
The price is P24,905
P47,645 total
includes taxes & fees
Sep 14 - Sep 15
Art Villa
Sonder by Marriott Bonvoy Greektown Apartments
Living room

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
8.6 out of 10, Excellent, (59)
"Great location, easy stay!"
The price is P12,088
P14,190 total
includes taxes & fees
Sep 4 - Sep 5
Sonder by Marriott Bonvoy Greektown Apartments
Ground Floor Studios in Chicago by 747 Lofts
Exterior

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
9.4 out of 10, Exceptional, (16)
"Its was in a good location for anyone who has family close by. Bed was wonderful. "
The price is P5,403
P10,328 total
includes taxes & fees
Sep 15 - Sep 16
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.
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Top Winnetka Hotel Reviews

citizenM Chicago Downtown

citizenM Chicago Downtown

10/10 Excellent
"The amenities are great at Citizen M! We loved the technology in the room being able to control the lights and temperature through the iPad. Easy check in and check out process, awesome that you get to choose what view you would like when you check in. Close to everything, very walkable! Staff was all friendly and accommodating, we would love to come back! "
Emma 3-night trip
Posted 8 hours ago
citizenM Chicago Downtown

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 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.