Winnetka Vacation Rentals

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Check prices for these dates

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Jul 8 - Jul 9
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Vacation Rentals in Winnetka

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (808)
"Great stay!"
The price is P10,553
P14,052 total
includes taxes & fees
Jul 9 - Jul 10
Sentral Michigan Avenue
Level Chicago – Old Town
Front of property - evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (324)
"Hotel was nice"
The price is P25,328
P30,998 total
includes taxes & fees
Jul 30 - Jul 31
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
8.4 out of 10, Very Good, (316)
"Super cool spot in a great part of the city."
The price is P9,581
P11,248 total
includes taxes & fees
Jul 16 - Jul 17
Sonder by Marriott Bonvoy Market Hall Apartments West 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, (438)
"Overall experience was great"
Kasa Magnificent Mile 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
8.8 out of 10, Excellent, (559)
"Great place and location. "
The price is P10,553
P12,389 total
includes taxes & fees
Jul 24 - Jul 25
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
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
9.0 out of 10, Wonderful, (193)
"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 P14,794
P17,367 total
includes taxes & fees
Jul 26 - Jul 27
Sonder by Marriott Bonvoy The Burnham Apartments Loop
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, (110)
"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 P9,581
P11,247 total
includes taxes & fees
Jul 13 - Jul 14
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
The Gem Museum Suites
Reception

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (70)
"Good people great breakfast "
The price is P11,582
P13,260 total
includes taxes & fees
Jul 9 - Jul 10
The Gem Museum Suites
The Neighborhood Hotel-Little Italy
Front of property

The Neighborhood Hotel-Little Italy

4.0 star property
9.8 out of 10, Exceptional, (173)
"Great spot. "
The Neighborhood Hotel-Little Italy
Kasa South Loop Chicago
City view

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (317)
"Great stay"
Kasa South Loop Chicago
Kasa River North Chicago
Library

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (154)
"Great stay, clean room!"
Kasa River North Chicago
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, (167)
"Great location and much larger space than I expected. Great location in the Loop with access to public transit and walkable. "
The price is P10,148
P11,913 total
includes taxes & fees
Jul 10 - Jul 11
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, (42)
"Our stay was amazing. "
The price is P11,035
P12,954 total
includes taxes & fees
Jul 27 - Jul 28
Sonder by Marriott Bonvoy The Opal Apartments River North
Wrigleyville Suites
Living area

Wrigleyville Suites

2.0 star property
9.2 out of 10, Wonderful, (7)
"Absolutely loved staying here! Would 10/10 recommend this place!"
The price is P4,133
P7,686 total
includes taxes & fees
Jul 9 - Jul 10
Wrigleyville Suites
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 P12,433
P14,595 total
includes taxes & fees
Jul 27 - Jul 28
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.