Winnetka Vacation Rentals

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Oct 23 - Oct 24
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Oct 24 - Oct 25
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Oct 31 - Nov 2

Vacation Rentals in Winnetka

Indoor pool
Sentral Michigan Avenue
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (961)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is ￥20,371
￥28,372 total
includes taxes & fees
Nov 10 - Nov 11
Sentral Michigan Avenue
Front of property - evening/night
Level Chicago – Old Town
Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (370)
"Friendly staff and great amenities "
United States
Bryan
The price is ￥31,147
￥39,954 total
includes taxes & fees
Nov 11 - Nov 12
Level Chicago – Old Town
50-inch flat-screen TV with digital channels, TV
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
3.5 star property
8.2 out of 10, Very Good, (185)
"Place was amazing! Very centralized, all sorts of restaurants nearby, and right next to the CTA Trains which is AWESOME!"
United States
Alexander
The price is ￥17,948
￥21,068 total
includes taxes & fees
Nov 10 - Nov 11
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Business center
Kasa River North Chicago
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (174)
"This place has everything for a multi-night stay."
United States
Dane
Kasa River North Chicago
Deluxe Apartment, City View | Hypo-allergenic bedding, iron/ironing board, travel crib, free WiFi
4BR Corporate Suite Central and Modern
4BR Corporate Suite Central and Modern
2.0 star property
10.0 out of 10, Exceptional, (4)
"We loved at our stay at this property. It was one of the best stays we have had on vacation."
United States
Javeria
The price is ￥21,331
￥56,961 total
includes taxes & fees
Oct 29 - Oct 30
4BR Corporate Suite Central and Modern
Studio | Private kitchen | Fridge, oven, coffee/tea maker, toaster
River West, Third Floor Chicago by 747 Lofts
River West, Third Floor Chicago by 747 Lofts
2.0 star property
9.0 out of 10, Wonderful, (17)
"Overall solid property, I will return."
United States
Fletcher
The price is ￥24,982
￥54,600 total
includes taxes & fees
Oct 31 - Nov 1
River West, Third Floor Chicago by 747 Lofts
Interior
Your Chicago get Away
Your Chicago get Away
8.4 out of 10, Very Good, (6)
"Clean, fun space and responsive host! Loved the views from our room!"
United States
Tyler C.
The price is ￥28,454
￥60,835 total
includes taxes & fees
Oct 28 - Oct 29
Your Chicago get Away
Interior
Twice as Nice: Chic 2BR Stay with Style & Space
Twice as Nice: Chic 2BR Stay with Style & Space
9.4 out of 10, Exceptional, (10)
"Had a very nice time in Chicago!"
United States
Valerie S.
The price is ￥15,647
￥35,365 total
includes taxes & fees
Oct 28 - Oct 29
Twice as Nice: Chic 2BR Stay with Style & Space
Fridge, microwave, oven, stovetop
Stylish 1BR in West Loop
Stylish 1BR in West Loop
10.0 out of 10, Exceptional, (7)
"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"
United States
Jacob D.
The price is ￥14,735
￥32,019 total
includes taxes & fees
Oct 27 - Oct 28
Stylish 1BR in West Loop
Fridge, microwave, oven, stovetop
Sun-Drenched 1BR Apartment
Sun-Drenched 1BR Apartment
10.0 out of 10, Exceptional, (1)
"The location was fantastic. We were just a couple blocks from the Green and Pink line on Clinton. There was a code to get into the building so it felt safe. The code to the door was great because there was no key to worry about since I had to work and my hubby was in and out of the apartment all day. There were a couple small things, the bed squeaks a lot. Also, it is very clear in the listing that the train is close. It is about 30ft straight out from the window. I'm not a light sleeper so I...
United States
Jennifer A.
The price is ￥14,735
￥32,019 total
includes taxes & fees
Oct 29 - Oct 30
Sun-Drenched 1BR Apartment
Interior
Cozy Gold Coast Studio Stay
Cozy Gold Coast Studio Stay
10.0 out of 10, Exceptional, (2)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is ￥14,735
￥30,689 total
includes taxes & fees
Oct 28 - Oct 29
Cozy Gold Coast Studio Stay
Interior
South Loop Rooftop With In & Out Parking 1
South Loop Rooftop With In & Out Parking 1
9.0 out of 10, Wonderful, (2)
"We loved the property! It was well kept, clean, with a seamless check in and check out process! I wish the parking garage would have been closer but otherwise everything was great! Shout out to the host for his promptness with all my questions! I would recommend this place if they are looking for a place to stay! "
United States
Bridney K.
The price is ￥31,903
￥69,543 total
includes taxes & fees
Oct 31 - Nov 1
South Loop Rooftop With In & Out Parking 1
1 bedroom, individually furnished, desk, iron/ironing board
Sonder by Marriott Bonvoy The Opal Apartments River North
Sonder by Marriott Bonvoy The Opal Apartments River North
3.5 star property
8.4 out of 10, Very Good, (54)
"Place was in a great location close to good restaurants "
United States
Charles
The price is ￥17,948
￥21,068 total
includes taxes & fees
Nov 10 - Nov 11
Sonder by Marriott Bonvoy The Opal Apartments River North
Fridge, microwave, oven, stovetop
The One: A 1BR Stay That Feels Like Home
The One: A 1BR Stay That Feels Like Home
9.0 out of 10, Wonderful, (2)
"Very nice condo in a quiet neighborhood"
Canada
Patrick
The price is ￥14,431
￥32,036 total
includes taxes & fees
Nov 3 - Nov 4
The One: A 1BR Stay That Feels Like Home
Fridge, microwave, oven, stovetop
River North Rooftop With In and Out Parking 5
River North Rooftop With In and Out Parking 5
10.0 out of 10, Exceptional, (2)
"Everything was amazing, property was even better than expected"
United States
Jacob
The price is ￥22,027
￥56,210 total
includes taxes & fees
Oct 29 - Oct 30
River North Rooftop With In and Out Parking 5
Fridge, microwave, oven, stovetop
West Loop Living – Bright 1BR
West Loop Living – Bright 1BR
The price is ￥14,735
￥32,019 total
includes taxes & fees
Oct 27 - Oct 28
West Loop Living – Bright 1BR
1 bedroom, WiFi, bed sheets
1BR Modern Luxe Apt with In-Unit Laundry
1BR Modern Luxe Apt with In-Unit Laundry
The price is ￥14,431
￥31,851 total
includes taxes & fees
Nov 3 - Nov 4
1BR Modern Luxe Apt with In-Unit Laundry
Living area
Wrigleyville Suites
Wrigleyville Suites
2.0 star property
9.6 out of 10, Exceptional, (24)
"The entirety of my experience was excellent. Thank you!"
United States
Julian
The price is ￥19,277
￥30,224 total
includes taxes & fees
Oct 24 - Oct 25
Wrigleyville Suites
Private kitchen
Spacious 3-bedroom apartment near downtown, FREE PARKING
Spacious 3-bedroom apartment near downtown, FREE PARKING
9.4 out of 10, Exceptional, (8)
"Nice place to stay. Good communication with the owner."
United States
Ryan
The price is ￥9,875
￥52,492 total
includes taxes & fees
Nov 17 - Nov 18
Spacious 3-bedroom apartment near downtown, FREE PARKING
Fridge, microwave, oven, stovetop
Chicago luxury home suites
Chicago luxury home suites
2.0 star property
The price is ￥148,112
￥173,869 total
includes taxes & fees
Oct 24 - Oct 25
Chicago luxury home suites
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

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"Great place to stay in the city!!! The room was super nice with an amazing city view and the end was just perfect !!! Housekeeping staff was outstanding and it was in a very downtown convenient area to walk and find everything around !!! Would come back for sure 10000%"
andrea 6-night trip
Posted 4 hours ago
Hilton Chicago/Magnificent Mile Suites

Find out more about Winnetka

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

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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 are some of the best vacation rentals in Winnetka?

Wrigley Field/Lakeview -Entire Home- Large Groups!: Visitors like this Winnetka vacation home rental. It is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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.