Winnetka Vacation Rentals

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Check prices for these dates

In two weeks
Oct 31 - Nov 2
In two months
Dec 12 - Dec 14
In three months
Jan 9 - Jan 11
In four months
Feb 6 - Feb 8

Vacation Rentals in Winnetka

Sentral Michigan Avenue
Indoor pool
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (955)
"Great location and cleanliness of rooms. Staff was extremely helpful "
The price is ₩192,601
₩267,917 total
includes taxes & fees
Nov 10 - Nov 11
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, (559)
"Very great place to stay!"
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, (367)
"Friendly staff and great amenities "
The price is ₩216,949
₩286,484 total
includes taxes & fees
Nov 3 - Nov 4
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, (382)
"Great stay!"
The price is ₩180,488
₩211,875 total
includes taxes & fees
Nov 2 - Nov 3
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, (239)
"Great stay. "
The price is ₩192,601
₩226,094 total
includes taxes & fees
Nov 2 - Nov 3
Sonder by Marriott Bonvoy The Burnham Apartments Loop
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, (687)
"great room, clean good space and close to places "
The price is ₩192,601
₩226,094 total
includes taxes & fees
Oct 29 - Oct 30
Sonder by Marriott Bonvoy South Wabash Apartments South 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, (363)
"nice area, shops nearby"
Kasa South Loop Chicago
The Neighborhood Hotel-Little Italy
Front of property
The Neighborhood Hotel-Little Italy
4.0 star property
9.6 out of 10, Exceptional, (210)
"Perfect location and area was wonderful."
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, (53)
"Place was in a great location close to good restaurants "
The price is ₩192,601
₩226,094 total
includes taxes & fees
Nov 9 - Nov 10
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, (171)
"This place has everything for a multi-night stay."
The price is ₩227,017
₩400,328 total
includes taxes & fees
Oct 19 - Oct 20
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, (90)
"Super nice hotel and staff "
The price is ₩283,450
₩324,493 total
includes taxes & fees
Oct 29 - Oct 30
The Gem Museum Suites
Wrigleyville Suites
Living area
Wrigleyville Suites
2.0 star property
9.8 out of 10, Exceptional, (21)
"Excellent location and very clean! Would stay again!"
The price is ₩96,194
₩184,178 total
includes taxes & fees
Oct 15 - Oct 16
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, (184)
"Place was amazing! Very centralized, all sorts of restaurants nearby, and right next to the CTA Trains which is AWESOME!"
The price is ₩168,374
₩197,656 total
includes taxes & fees
Nov 9 - Nov 10
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
The price is ₩283,593
₩491,835 total
includes taxes & fees
Oct 16 - Oct 17
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, (144)
"Very clean and affordable "
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Sonder by Marriott Bonvoy Greektown Apartments
Apartment, 1 Bedroom | Living room | 40-inch flat-screen TV with digital channels, TV
Sonder by Marriott Bonvoy Greektown Apartments
3.5 star property
8.6 out of 10, Excellent, (65)
"The kitchen had everything we needed, great space overall, safe location, clean, near everything we needed, access to bus and rail very close, we really enjoyed our stay. "
The price is ₩241,054
₩282,974 total
includes taxes & fees
Nov 2 - Nov 3
Sonder by Marriott Bonvoy Greektown Apartments
Art Villa
Design Townhome, 3 Bedrooms, Kitchen, City View | Terrace/patio
Art Villa
5.0 star property
10.0 out of 10, Exceptional, (2)
" "
The price is ₩691,312
₩1,360,405 total
includes taxes & fees
Oct 15 - Oct 16
Art Villa
Ground Floor Studios in Chicago by 747 Lofts
Exterior
Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
9.2 out of 10, Wonderful, (19)
"The stay lacked in shelf space as well as other amenities that could be useful. "
The price is ₩150,746
₩400,351 total
includes taxes & fees
Oct 23 - Oct 24
Ground Floor Studios in Chicago by 747 Lofts
At Home in Oak Park
Apartment, Private Bathroom | Terrace/patio
At Home in Oak Park
3.5 star property
9.8 out of 10, Exceptional, (7)
"Great location in Oak Park- walkable, wondering area for restaurants and strolling through the beautiful neighborhoods."
The price is ₩210,272
₩378,946 total
includes taxes & fees
Nov 2 - Nov 3
At Home in Oak Park
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

Freehand Chicago

Freehand Chicago

10/10 Excellent
"Convenient location with very helpful staff! "
James 2-night trip
Posted 6 hours ago
Freehand Chicago

Find out more about Winnetka

Search for Vacation rentals in Winnetka on Expedia.co.uk! You can easily find your home rentals, villas, Vacation apartments in Winnetka using one of the methods below:

  • View our selection of featured Vacation rentals in Winnetka
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Look no further and take a look at our great range of rental properties in Winnetka!

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.