Title: Winnetka Vacation Rentals from CA $118: Short-Term Rentals for 2025 | Expedia.ca

 

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# Winnetka Vacation Rentals

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## Check prices for these dates

Tonight

[Nov 3 - Nov 4](https://www.expedia.ca/Hotel-Search?regionId=175751&startDate=2025-11-03&endDate=2025-11-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Nov 4 - Nov 5](https://www.expedia.ca/Hotel-Search?regionId=175751&startDate=2025-11-04&endDate=2025-11-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=175751&startDate=2025-11-07&endDate=2025-11-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=175751&startDate=2025-11-14&endDate=2025-11-16&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Vacation Rentals in Winnetka

![Indoor pool](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/a9b3121a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio, 1 Queen Bed (Studio Apartment) | Private kitchen](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/1bf06d5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Apartment, 2 Bedrooms | Living area](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/ecc0a878.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lounge](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/eacd6d88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sentral Michigan Avenue

Downtown Chicago

9.2/10

Wonderful

(972)

"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Nicole

CA $188

CA $262 total

includes taxes & fees

Nov 10 - Nov 11

[](https://www.expedia.ca/Chicago-Hotels-Sentral-Michigan-Avenue.h76267438.Hotel-Information)

![50-inch flat-screen TV with digital channels, TV](https://images.trvl-media.com/lodging/65000000/64880000/64871100/64871080/d10a452f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![50-inch flat-screen TV with digital channels, TV](https://images.trvl-media.com/lodging/65000000/64880000/64871100/64871080/851ef6de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/65000000/64880000/64871100/64871080/36238ab8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, individually decorated, individually furnished](https://images.trvl-media.com/lodging/65000000/64880000/64871100/64871080/dac97393.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

Downtown Chicago

8.2/10

Very good

(187)

"Place was amazing! Very centralized, all sorts of restaurants nearby, and right next to the CTA Trains which is AWESOME!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Alexander

CA $154

CA $180 total

includes taxes & fees

Nov 16 - Nov 17

[](https://www.expedia.ca/Chicago-Hotels-Sonder-At-Jewelers-Row.h64871080.Hotel-Information)

![Business centre](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/825d44e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cafe](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/715d8399.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![BBQ/picnic area](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/860305fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/f7e5c565_edited_04eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kasa River North Chicago

Downtown Chicago

9.4/10

Exceptional

(175)

"Awesome stay "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sally

CA $188

CA $352 total

includes taxes & fees

Nov 12 - Nov 13

[](https://www.expedia.ca/Chicago-Hotels-Kasa-River-North-Chicago.h66425311.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793104/e4126779.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793104/53fb8853.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793104/964f82ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793104/61009377.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Twice as Nice: Chic 2BR Stay with Style & Space

Downtown Chicago

9.6/10

Exceptional

(13)

"Had a very nice time in Chicago!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Valerie S.

CA $136

CA $323 total

includes taxes & fees

Nov 11 - Nov 12

[](https://www.expedia.ca/Chicago-Hotels-Twice-As-Nice-Chic-2BR-Stay-With-Style-Space.h116793104.Hotel-Information)

![Front of property - evening/night](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/a7a120b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/cb208a99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Flat-screen TV](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/9bdb478c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Level Chicago – Old Town

Downtown Chicago

9.0/10

Wonderful

(375)

"Great place to stay. Loved it!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Peter

CA $292

CA $374 total

includes taxes & fees

Nov 11 - Nov 12

[](https://www.expedia.ca/Chicago-Hotels-LEVEL-Furnished-Living-Chicago.h39805843.Hotel-Information)

![Desk, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/0412ba3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/89ec4d06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/04543f0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/2ed4b8ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Gold Coast Studio Stay

Downtown Chicago

10/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Seynabou

CA $97

CA $232 total

includes taxes & fees

Nov 4 - Nov 5

[](https://www.expedia.ca/Chicago-Hotels-Cozy-Gold-Coast-Studio-Stay.h120508888.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/c52efc06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/b754723c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/664fb229.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119140000/119131900/119131874/368bd483.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### West Loop Living – Bright 1BR

Downtown Chicago

10/10

Exceptional

(1)

"Thorough and easy to follow parking and check in instructions. Clean apartment. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kira V.

CA $101

CA $251 total

includes taxes & fees

Nov 4 - Nov 5

[](https://www.expedia.ca/Chicago-Hotels-West-Loop-Living-Bright-1BR.h119131874.Hotel-Information)

![Business Apartment, City View | Private kitchen](https://images.trvl-media.com/lodging/119000000/118640000/118632100/118632066/0374aa13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/119000000/118640000/118632100/118632066/9649f522.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Apartment, City View](https://images.trvl-media.com/lodging/119000000/118640000/118632100/118632066/6a748c36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Apartment, City View | Living area](https://images.trvl-media.com/lodging/119000000/118640000/118632100/118632066/06fff62f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 4BR Corporate Suite Central and Modern

Near North Side

10/10

Exceptional

(6)

"Great location in Lincoln Park. Easy walk to several shops and restaurants. And about a 5 minute walk to the redline station (North/Clybourn). Very clean and quiet inside the unit. Building is very new. Room access through the Latch app is simple. I would definitely stay here again. The overall experience was excellent and my other guests would agree. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Phillip

CA $164

CA $487 total

includes taxes & fees

Nov 6 - Nov 7

[](https://www.expedia.ca/Chicago-Hotels-4BR-Corporate-Suite-Central-And-Modern.h118632066.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/a49da56a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/003c4277.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/c3fddccc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792936/6b9648de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sun-Drenched 1BR Apartment

Downtown Chicago

10/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jennifer A.

CA $101

CA $251 total

includes taxes & fees

Nov 5 - Nov 6

[](https://www.expedia.ca/Chicago-Hotels-Sun-Drenched-1BR-Apartment.h116792936.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793110/50bbce16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793110/3815ff36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793110/fd6dad17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793110/640a9e62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The One: A 1BR Stay That Feels Like Home

Downtown Chicago

9.4/10

Exceptional

(3)

"Very nice condo in a quiet neighborhood"

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Patrick

CA $101

CA $251 total

includes taxes & fees

Nov 4 - Nov 5

[](https://www.expedia.ca/Chicago-Hotels-All-Set-Up-Furnished-1BR-Unit.h116793110.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/3cc0a9a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/89a0d93e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/9b704ea8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793043/f642030c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stylish 1BR in West Loop

Downtown Chicago

10/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jacob D.

CA $101

CA $251 total

includes taxes & fees

Nov 4 - Nov 5

[](https://www.expedia.ca/Chicago-Hotels-Stylish-1BR-In-West-Loop.h116793043.Hotel-Information)

![1 bedroom, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/92000000/91690000/91683200/91683158/e3b8d058.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Full-size fridge, electric kettle, cookware/dishes/utensils](https://images.trvl-media.com/lodging/92000000/91690000/91683200/91683158/a5314f63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![50-inch flat-screen TV with digital channels, TV, streaming services](https://images.trvl-media.com/lodging/92000000/91690000/91683200/91683158/a9095b05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![50-inch flat-screen TV with digital channels, TV, streaming services](https://images.trvl-media.com/lodging/92000000/91690000/91683200/91683158/ea846735.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Downtown Chicago

8.0/10

Very good

(396)

"Quite and low key spot"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Shunica

CA $142

CA $166 total

includes taxes & fees

Nov 17 - Nov 18

[](https://www.expedia.ca/Sonder-Market-Hall.h91683158.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712536/73f1c663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712536/360842b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712536/5da8154a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712536/a80d9e55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### River North Rooftop With In and Out Parking 5

Downtown Chicago

10/10

Exceptional

(2)

"As advertised. Beautiful, well appointed apartment. Centrally located to restaurants, shopping and the L train. Hosts were very communicative and attentive to our needs. Highly recommend. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Mike S.

CA $241

CA $569 total

includes taxes & fees

Nov 16 - Nov 17

[](https://www.expedia.ca/Chicago-Hotels-River-North-Rooftop-With-In-Out-Parking-5.h117712536.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712525/21564a39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712525/0b5cf1fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712525/a8c42a70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/118000000/117720000/117712600/117712525/3da49e9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### South Loop Rooftop With In and Out Parking 3

Downtown Chicago

8.0/10

Very good

(3)

"Modern and stylish apartment in a great location. Lots of extra thoughtful touches made it a great stay. "

![Australia](https://a.travel-assets.com/egds/marks/flags/au.svg)

Angela M.

CA $179

CA $486 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Chicago-Hotels-South-Loop-Rooftop-With-In-Out-Parking.h117712525.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792754/1310976f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792754/716fc9f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792754/a190b9fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792754/2bfb9517.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Complete 1BR Home Sum

Downtown Chicago

CA $109

CA $264 total

includes taxes & fees

Nov 11 - Nov 12

[](https://www.expedia.ca/Chicago-Hotels-1BR-Chic-Equipped-Apt.h116792754.Hotel-Information)

![Studio | Exterior](https://images.trvl-media.com/lodging/89000000/88910000/88902400/88902334/75e5b633.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | Living area](https://images.trvl-media.com/lodging/89000000/88910000/88902400/88902334/9718e304.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | View from property](https://images.trvl-media.com/lodging/89000000/88910000/88902400/88902334/da815e3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | Living area](https://images.trvl-media.com/lodging/89000000/88910000/88902400/88902334/f9632e6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chicago Third Floor Studio by 747 Lofts

West Town

9.6/10

Exceptional

(5)

"Cute little studio that was clean. There was a nice size kitchen and was close to our activities in the West loop of Chicago. There was also assistance with parking located in the lofts."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jennifer

CA $86

CA $310 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Chicago-Hotels-Walk-To-Local-Hot-Spots-Or-Public-Transit-Prime-Location-In-The-Heart-Of-The-Windy-City-747-Lofts-Cabin-301-Hotel-Room.h88902334.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793107/939f8498.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793107/0ec6dac1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793107/c1cc9a6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793107/a9804ae4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sleek 1BR Apt w/ Laundry

Downtown Chicago

10/10

Exceptional

(1)

"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Anonymous traveller

CA $122

CA $281 total

includes taxes & fees

Nov 19 - Nov 20

[](https://www.expedia.ca/Chicago-Hotels-Sleek-1BR-Apt-W-Laundry.h116793107.Hotel-Information)

![Free WiFi](https://images.trvl-media.com/lodging/122000000/121430000/121424500/121424489/740de96f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free WiFi](https://images.trvl-media.com/lodging/122000000/121430000/121424500/121424489/d5ea6c7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/122000000/121430000/121424500/121424489/e66c238f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/122000000/121430000/121424500/121424489/23b1a020.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chicago luxury home suites

Downtown Chicago

10/10

Exceptional

(1)

"This was Amazing stay I have ever had in my life. Wonderful host, super clean. Stunning views, close to everything that you would needed. "

![New Zealand](https://a.travel-assets.com/egds/marks/flags/nz.svg)

Moha

CA $1,366

CA $1,604 total

includes taxes & fees

Nov 4 - Nov 5

[](https://www.expedia.ca/Chicago-Hotels-Chicago-Luxury-Home-Suites.h121424489.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/117000000/116030000/116024600/116024537/4dadbd09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116030000/116024600/116024537/fe7fd7f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/117000000/116030000/116024600/116024537/92ec7bf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116030000/116024600/116024537/acc0487e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious 3-bedroom apartment near downtown, FREE PARKING

Near West Side

9.4/10

Exceptional

(8)

"Nice place to stay. Good communication with the owner."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ryan

CA $81

CA $470 total

includes taxes & fees

Nov 4 - Nov 5

[](https://www.expedia.ca/Chicago-Hotels-Spacious-3-Bedroom-Apartment-Near-Downtown.h116024537.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/06060406.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/3e6dada5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/2626f596.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/5dcfd7fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wrigleyville Suites

Lakeview

9.6/10

Exceptional

(26)

"Excellent location and very clean! Would stay again!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jacob

CA $101

CA $118 total

includes taxes & fees

Nov 4 - Nov 5

[](https://www.expedia.ca/Chicago-Hotels-Wrigleyville-Suites.h104315648.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-17&endDate=2025-11-18&regionId=175751&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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Save an average of 15% on thousands of hotels when you're signed in

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## Top Winnetka Hotel Reviews

![Hilton Garden Inn Chicago Downtown/Magnificent Mile](//images.trvl-media.com/lodging/1000000/430000/424200/424187/d51caee8_y.jpg)

### Hilton Garden Inn Chicago Downtown/Magnificent Mile

10/10 Excellent

"Clean rooms and friendly staff"

[](https://expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-DowntownMagnificent-Mile.h424187.Hotel-Information)

![Hotel Riu Plaza Chicago](//images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg)

### Hotel Riu Plaza Chicago

10/10 Excellent

"The staff here was super friendly and helpful! Loved how they decorated the lobby for Halloween. Overall a great hotel. "

[](https://expedia.ca/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.Hotel-Information)

![Sable at Navy Pier Chicago, Curio Collection by Hilton](//images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg)

### Sable at Navy Pier Chicago, Curio Collection by Hilton

10/10 Excellent

"Great location on Navy Pier. Just a few steps away from boat tours and 10 minute walk to downtown. Excellent room, especially liked the big chair to look out the window at Lake Michigan and the fabulous Chicago skyline. Hotel staff were very nice. Restaurant and bar were good. "

[](https://expedia.ca/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information)

![Hotel Felix River North/Magnificent Mile](//images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d46a8a4d_y.jpg)

### Hotel Felix River North/Magnificent Mile

10/10 Excellent

"Great"

[](https://expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information)

![The Allegro Royal Sonesta Hotel Chicago Loop](//images.trvl-media.com/lodging/1000000/40000/34500/34496/69c2e798_y.jpg)

### The Allegro Royal Sonesta Hotel Chicago Loop

10/10 Excellent

"Good service "

[](https://expedia.ca/Chicago-Hotels-The-Allegro-Royal-Sonesta-Hotel.h34496.Hotel-Information)

![Freehand Chicago](//images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c_y.jpg)

### Freehand Chicago

10/10 Excellent

"Staff interactions were excellent in every aspect. "

[](https://expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information)

![Hilton Chicago/Magnificent Mile Suites](//images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg)

### Hilton Chicago/Magnificent Mile Suites

10/10 Excellent

"Great staff at the front desk!"

[](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information)

![The Whitehall Hotel, BW Premier Collection](//images.trvl-media.com/lodging/1000000/20000/18000/17903/daaf5f2e_y.jpg)

### The Whitehall Hotel, BW Premier Collection

10/10 Excellent

"Best upon arrival and the staff promptly answered any and all concerns"

[](https://expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information)

![Palmer House a Hilton Hotel](//images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg)

### Palmer House a Hilton Hotel

10/10 Excellent

"Room was very clean and well kept"

[](https://expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information)

## Find out more about Winnetka

**Everything you need to know about** **Winnetka** **vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winnetka vacation rental for you. At Expedia, you can take your pick from [private vacation homes](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winnetka vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

**Winnetka vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Winnetka. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winnetka vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winnetka vacation rentals we have selected for you start as low as CA $118 per night. Entering your travel dates in the search wizard you might find even better deals!

**How to find incredible deals on Winnetka rentals**

At Expedia, we put the best Winnetka vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winnetka rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winnetka vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winnetka. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

## Explore a world of travel with Expedia

-   Trending destinations on Expedia.ca
-   All accommodation types in Winnetka

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-   [Ontario Vacation Rentals](https://www.expedia.ca/Destinations-In-Ontario.d11178.Vacation-Rental-Destinations)
-   [British Columbia Vacation Rentals](https://www.expedia.ca/Destinations-In-British-Columbia.d11117.Vacation-Rental-Destinations)
-   [Prince Edward Island Vacation Rentals](https://www.expedia.ca/Destinations-In-Prince-Edward-Island.d6058122.Vacation-Rental-Destinations)
-   [Québec Vacation Rentals](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals)

-   [Apartments in Winnetka](https://expedia.ca/Winnetka-Apartments.d175751-aaApartments.Travel-Guide-Accommodation)
-   [Vacation Homes in Winnetka](https://expedia.ca/Winnetka-Private-Vacation-Homes.d175751-aaPrivateVacationHomes.Travel-Guide-Accommodation)
-   [Condo Rentals in Winnetka](https://expedia.ca/Winnetka-Condos.d175751-aaCondos.Travel-Guide-Accommodation)
-   [Aparthotels in Winnetka](https://expedia.ca/Winnetka-Apart-Hotels.d175751-aaApartHotels.Travel-Guide-Accommodation)
-   [Motels in Winnetka](https://expedia.ca/Winnetka-Motels.d175751-aaMotels.Travel-Guide-Accommodation)
-   [B&B in Winnetka](https://expedia.ca/Winnetka-Bed-And-Breakfast.d175751-aaBedAndBreakfast.Travel-Guide-Accommodation)
-   [Cottages in Winnetka](https://expedia.ca/Winnetka-Cottages.d175751-aaCottages.Travel-Guide-Accommodation)
-   [Guest Houses in Winnetka](https://expedia.ca/Winnetka-Guest-Houses.d175751-aaGuestHouses.Travel-Guide-Accommodation)
-   [Hostels in Winnetka](https://expedia.ca/Winnetka-Hostels.d175751-aaHostels.Travel-Guide-Accommodation)
-   [Villas in Winnetka](https://expedia.ca/Winnetka-Villas.d175751-aaVillas.Travel-Guide-Accommodation)
-   [Resorts in Winnetka](https://expedia.ca/Winnetka-Resort-Hotels.d175751-aaResortHotels.Travel-Guide-Accommodation)
-   [Cabin Rentals in Winnetka](https://expedia.ca/Winnetka-Cabins.d175751-aaCabins.Travel-Guide-Accommodation)
-   [Houseboats in Winnetka](https://expedia.ca/Winnetka-Houseboats.d175751-aaHouseboats.Travel-Guide-Accommodation)
-   [Inns in Winnetka](https://expedia.ca/Winnetka-Inns.d175751-aaInns.Travel-Guide-Accommodation)
-   [Residences in Winnetka](https://expedia.ca/Winnetka-Residences.d175751-aaResidences.Travel-Guide-Accommodation)

## 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?

> [Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed](https://www.expedia.ca/Chicago-Hotels-Charming-2-Bedroom-House-In-Maywood-With-WiFi.h117671933.Hotel-Information): Visitors like this Winnetka vacation home rental. It offers a patio, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave.

### 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.

![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg)

## Go further with the Expedia app

Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app

![QR code to download the app](data:image/png;base64,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)