Title: Winnetka Vacation Home Rentals from CA $274: Search Top Private Vacation Homes for Rent | Expedia.ca

[Winnetka Travel Guide](https://expedia.ca/Winnetka.dx175751)[Hotels in Winnetka](https://expedia.ca/Winnetka-Hotels.d175751.Travel-Guide-Hotels)[Vacation Rentals in Winnetka](https://expedia.ca/Winnetka-Vacation-Rentals.d175751.Travel-Guide-VacationRentals)[Flights to Winnetka](https://expedia.ca/Cheap-Flights-To-Winnetka.d175751.Travel-Guide-Flights)[Winnetka Car Rentals](https://expedia.ca/Car-Rentals-In-Winnetka.d175751.Car-Rental-Guide)[Winnetka Vacation Packages](https://expedia.ca/Winnetka.d175751.Destination-Travel-Guides)

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## Check prices for these dates

In two weeks

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=175751&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=175751&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 26 - Jun 28](https://www.expedia.ca/Hotel-Search?regionId=175751&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 24 - Jul 26](https://www.expedia.ca/Hotel-Search?regionId=175751&startDate=2026-07-24&endDate=2026-07-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Winnetka vacation homes

![Exterior detail](https://images.trvl-media.com/lodging/33000000/32070000/32068000/32067984/7966b3f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/33000000/32070000/32068000/32067984/2718fcef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, books](https://images.trvl-media.com/lodging/33000000/32070000/32068000/32067984/3e0125af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/33000000/32070000/32068000/32067984/5445a025.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quaint Bungalow, near Great Lakes Naval Base

[](https://www.expedia.ca/Chicago-Hotels-Quaint-Bungalow.h32067984.Hotel-Information)

Mundelein

9.8/10

Exceptional

(69 reviews)

"We had a great stay! The area was peaceful and felt safe. "

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

Yoselin V.

CA $188

CA $465 total

includes taxes & fees

Apr 21 - Apr 22

[](https://www.expedia.ca/Chicago-Hotels-Quaint-Bungalow.h32067984.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/49000000/48960000/48959700/48959659/591973f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/49000000/48960000/48959700/48959659/ca60baaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/49000000/48960000/48959700/48959659/079e5c97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/49000000/48960000/48959700/48959659/76fecaef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Master qtr close to nature & easy urban facilities

[](https://www.expedia.ca/Chicago-Hotels-Master-Qtr-Close-To-Nature-Easy-Urban-Facilities.h48959659.Hotel-Information)

Riverwoods

9.8/10

Exceptional

(78 reviews)

"Had a lovely stay in a beautiful home! The setting is very secluded and quiet."

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

Kyle M.

CA $137

CA $274 total

includes taxes & fees

Apr 9 - Apr 10

[](https://www.expedia.ca/Chicago-Hotels-Master-Qtr-Close-To-Nature-Easy-Urban-Facilities.h48959659.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/118000000/117680000/117672000/117671933/afb1f08b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/118000000/117680000/117672000/117671933/b132ab29_edited_0386.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117680000/117672000/117671933/08f64820.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/118000000/117680000/117672000/117671933/52299e38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 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)

Maywood

8.2/10

Very good

(22 reviews)

"Easy to access, big place, great for a group that needs to have several rooms and beds. Would definitely stay again"

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

JOSE S.

CA $207

CA $419 total

includes taxes & fees

Apr 15 - Apr 16

[](https://www.expedia.ca/Chicago-Hotels-Charming-2-Bedroom-House-In-Maywood-With-WiFi.h117671933.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/106000000/105140000/105136600/105136524/33378924.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/106000000/105140000/105136600/105136524/aa9396b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/106000000/105140000/105136600/105136524/3f6e4959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/106000000/105140000/105136600/105136524/c4f6c687.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vintage Urban Retreat

[](https://www.expedia.ca/Chicago-Hotels-Vintage-Urban-Retreat.h105136524.Hotel-Information)

Oak Park

10/10

Exceptional

(14 reviews)

"The house was spotless and very comfortable for our needs. Best of all it was not far from our son’s home in River Forest which made going back and forth convenient."

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

Beryl I.

CA $282

CA $766 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Chicago-Hotels-Vintage-Urban-Retreat.h105136524.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101430000/101422200/101422169/4561d645.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/102000000/101430000/101422200/101422169/da0c68f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, offices](https://images.trvl-media.com/lodging/102000000/101430000/101422200/101422169/5b29180e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/102000000/101430000/101422200/101422169/4a2e2d54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 4BR Near Woodfield Mall & Metra | LCP Collection

[](https://www.expedia.ca/Chicago-Hotels-4BR-Near-Woodfield-Mall-Metra-LCP-Collection.h101422169.Hotel-Information)

Schaumburg

8.4/10

Very good

(5 reviews)

"Home was perfect for us with two kids. Beds were comfortable and a nice quiet location."

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

Randy G.

CA $239

CA $706 total

includes taxes & fees

Apr 8 - Apr 9

[](https://www.expedia.ca/Chicago-Hotels-4BR-Near-Woodfield-Mall-Metra-LCP-Collection.h101422169.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/97000000/96390000/96384200/96384152/baf1fbd0.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/97000000/96390000/96384200/96384152/02ca8784.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/97000000/96390000/96384200/96384152/f7e53c4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96390000/96384200/96384152/27ecf0e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### LUXE 3 BR, 2 BA + Hot Tub

[](https://www.expedia.ca/Chicago-Hotels-LUXE-3-BR.h96384152.Hotel-Information)

Elmhurst

8.8/10

Excellent

(40 reviews)

"Nice place, alot of space. Great host"

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

Devonta J.

CA $157

CA $403 total

includes taxes & fees

Apr 6 - Apr 7

[](https://www.expedia.ca/Chicago-Hotels-LUXE-3-BR.h96384152.Hotel-Information)

![Smart TV, fireplace, offices](https://images.trvl-media.com/lodging/105000000/104500000/104496900/104496834/a43944f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, offices](https://images.trvl-media.com/lodging/105000000/104500000/104496900/104496834/2a921aed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/105000000/104500000/104496900/104496834/e34c3bfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, offices](https://images.trvl-media.com/lodging/105000000/104500000/104496900/104496834/531c2789.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard

[](https://www.expedia.ca/Chicago-Hotels-2-Car-Garage-Access-Cal-King-Bed-Fenced-Yard.h104496834.Hotel-Information)

Arlington Heights

9.0/10

Wonderful

(6 reviews)

"Host was very responsive. Location was perfect for what we needed.Really liked having a garage for the car."

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

Katie C.

CA $302

CA $681 total

includes taxes & fees

Apr 6 - Apr 7

[](https://www.expedia.ca/Chicago-Hotels-2-Car-Garage-Access-Cal-King-Bed-Fenced-Yard.h104496834.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90010000/90008300/90008221/6ff9d9ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/91000000/90010000/90008300/90008221/dfe845a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90010000/90008300/90008221/b41a793a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90010000/90008300/90008221/35aa2d12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury House minutes away from O'Hare and Downtown Chicago

[](https://www.expedia.ca/Chicago-Hotels-Luxury-House-Minutes-Away-From-OHare-And-Downtown-Chicago.h90008221.Hotel-Information)

Bensenville

10/10

Exceptional

(1 review)

"Easily the nicest place I have ever stayed at. Wonderful neighborhood, clean house, and great amenities. I’ll stay there again anyday. "

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

Jacob F.

CA $303

CA $873 total

includes taxes & fees

Apr 6 - Apr 7

[](https://www.expedia.ca/Chicago-Hotels-Luxury-House-Minutes-Away-From-OHare-And-Downtown-Chicago.h90008221.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/91000000/90620000/90612900/90612832/793bb6f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/91000000/90620000/90612900/90612832/94169926.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90620000/90612900/90612832/0900c857.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, travel crib, free WiFi](https://images.trvl-media.com/lodging/91000000/90620000/90612900/90612832/cb5bf3e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Oak Park Victorian by FLW Studio

[](https://www.expedia.ca/Chicago-Hotels-Modern-Victorian-Vibes-Character-Charm.h90612832.Hotel-Information)

Oak Park

10/10

Exceptional

(29 reviews)

"Finding a good 3 br or 4 br option in and around OP / RF is challenging and if this one is available, jump on it. Functional plan, easy parking, great location and responsive owners. "

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

Lawrence P.

CA $262

CA $740 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Chicago-Hotels-Modern-Victorian-Vibes-Character-Charm.h90612832.Hotel-Information)

![Smart TV, offices](https://images.trvl-media.com/lodging/119000000/118080000/118074500/118074409/7199850c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/119000000/118080000/118074500/118074409/cbb8c9b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/119000000/118080000/118074500/118074409/53707240.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/119000000/118080000/118074500/118074409/d2a4fb64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Navy retreat near Naval Base-Tiki Bar,Sauna,Games

[](https://www.expedia.ca/Chicago-Hotels-Modern-Upgrade-Near-Navel-Base-Sauna.h118074409.Hotel-Information)

North Chicago

10/10

Exceptional

(22 reviews)

"Nice clean home, easy check in processes close to the base. Perfect for our stay with kids. "

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

Thomas D.

CA $273

CA $688 total

includes taxes & fees

Apr 6 - Apr 7

[](https://www.expedia.ca/Chicago-Hotels-Modern-Upgrade-Near-Navel-Base-Sauna.h118074409.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/121000000/120610000/120600500/120600426/4352f7f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/121000000/120610000/120600500/120600426/8b6cc65c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/121000000/120610000/120600500/120600426/w1152h659x0y118-58a7c14f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/121000000/120610000/120600500/120600426/ce40580f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Des Plaines / Chicago Midcentury 2-Bedroom Guesthouse

[](https://www.expedia.ca/Chicago-Hotels-Des-Plaines-Chicago-Midcentury-2-Bedroom-Guesthouse.h120600426.Hotel-Information)

Des Plaines

CA $244

CA $505 total

includes taxes & fees

Apr 8 - Apr 9

[](https://www.expedia.ca/Chicago-Hotels-Des-Plaines-Chicago-Midcentury-2-Bedroom-Guesthouse.h120600426.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811939/f0d5c893.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811939/66cebc67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811939/f1a28881.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811939/d22bbf58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Game Room • Fire-pit • Playground • Gym • Billiard

[](https://www.expedia.ca/Chicago-Hotels-Game-Room-Fire-Pit-Playground-Gym-Billiard.h122811939.Hotel-Information)

Belmont Cragin

CA $151

CA $675 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Chicago-Hotels-Game-Room-Fire-Pit-Playground-Gym-Billiard.h122811939.Hotel-Information)

![Smart TV, fireplace, books, video library](https://images.trvl-media.com/lodging/90000000/89740000/89733700/89733678/374225f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89740000/89733700/89733678/4834f018.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/90000000/89740000/89733700/89733678/82099dee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89740000/89733700/89733678/4ec2f70e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS

[](https://www.expedia.ca/Chicago-Hotels-Luxe-Haus-Of-LoveRenovated-1938-Cape-Cod-Heated-FLRS.h89733678.Hotel-Information)

Skokie

10/10

Exceptional

(36 reviews)

"Beautiful property, great location, quiet, with plenty of curb parking directly in front. "

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

carlos l.

CA $448

CA $973 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Chicago-Hotels-Luxe-Haus-Of-LoveRenovated-1938-Cape-Cod-Heated-FLRS.h89733678.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/124000000/123480000/123479400/123479305/d658c7db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/124000000/123480000/123479400/123479305/d30bfd55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/124000000/123480000/123479400/123479305/d0b74272.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/124000000/123480000/123479400/123479305/a541fdcd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard

[](https://www.expedia.ca/Chicago-Hotels-Charming-2BR-Hideaway-FLW-District-TheaterGamesLaundryOfficePrivate-Backyard.h123479305.Hotel-Information)

Oak Park

10/10

Exceptional

(2 reviews)

"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."

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

Willow M.

CA $231

CA $435 total

includes taxes & fees

Apr 12 - Apr 13

[](https://www.expedia.ca/Chicago-Hotels-Charming-2BR-Hideaway-FLW-District-TheaterGamesLaundryOfficePrivate-Backyard.h123479305.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/89000000/88080000/88074600/88074505/2e5468d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, travel crib, free WiFi](https://images.trvl-media.com/lodging/89000000/88080000/88074600/88074505/30a811e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/89000000/88080000/88074600/88074505/e884edf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/89000000/88080000/88074600/88074505/58422f17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chic 3bed 2bath Home with free parking close to United Center 

[](https://www.expedia.ca/Chicago-Hotels-Urban-Chic-Home-With-Free-Parking.h88074505.Hotel-Information)

Oak Park

9.8/10

Exceptional

(18 reviews)

"Overall just great lovely area and chill place, rooms was great and I love the Roku tvs to sit back In chill!"

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

Chantrice A.

CA $313

CA $943 total

includes taxes & fees

Apr 6 - Apr 7

[](https://www.expedia.ca/Chicago-Hotels-Urban-Chic-Home-With-Free-Parking.h88074505.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/125000000/124580000/124574000/124573977/12d7a004.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/125000000/124580000/124574000/124573977/21447f9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/125000000/124580000/124574000/124573977/584b3b88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/125000000/124580000/124574000/124573977/484953c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern 3-bedroom house in tranquil North Chicago near Great Lakes Navy Base

[](https://www.expedia.ca/Chicago-Hotels-Modern-3-Bedroom-House-In-Tranquil-North-Chicago-Near-Great-Lakes-Navy-Base.h124573977.Hotel-Information)

North Chicago

10/10

Exceptional

(1 review)

"Rented this property for my sons navy graduation, Base was only 6 minutes from the home. Tons of places to eat and shop no more then 15 minutes away. The house was super cute, very clean. we flew in at 10am and without even having to ask the host reached out and let us know it was ready for check in a few hours early which was great. left some packaged up congrats grad decor that hopefully didnt get thrown out and the next navy fam can use. "

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

Linda U.

CA $251

CA $557 total

includes taxes & fees

Apr 6 - Apr 7

[](https://www.expedia.ca/Chicago-Hotels-Modern-3-Bedroom-House-In-Tranquil-North-Chicago-Near-Great-Lakes-Navy-Base.h124573977.Hotel-Information)

![Fireplace](https://images.trvl-media.com/lodging/114000000/113430000/113424300/113424225/35b3a204_edited_bda3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113430000/113424300/113424225/6a755c90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113430000/113424300/113424225/w1200h798x0y5-177b5483.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/114000000/113430000/113424300/113424225/8950b29d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### King Bed, Game Room & Fire Pit | LCP Collection

[](https://www.expedia.ca/Chicago-Hotels-King-Bed.h113424225.Hotel-Information)

Westchester

8.0/10

Very good

(3 reviews)

"Great location, price and the place was well kept and accommodating."

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

Carl M.

CA $310

CA $705 total

includes taxes & fees

Apr 6 - Apr 7

[](https://www.expedia.ca/Chicago-Hotels-King-Bed.h113424225.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/97000000/96690000/96685300/96685294/d3b24fe7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/97000000/96690000/96685300/96685294/dad32a41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/97000000/96690000/96685300/96685294/90a99332.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96690000/96685300/96685294/39dd5566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Your Next Vacation Home

[](https://www.expedia.ca/Chicago-Hotels-Your-Next-Vacation-Home.h96685294.Hotel-Information)

Oakton

9.4/10

Exceptional

(69 reviews)

"We enjoyed our stay"

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

Lukose K.

CA $201

CA $415 total

includes taxes & fees

Apr 27 - Apr 28

[](https://www.expedia.ca/Chicago-Hotels-Your-Next-Vacation-Home.h96685294.Hotel-Information)

![Paper towels, dining tables](https://images.trvl-media.com/lodging/105000000/104500000/104497000/104496991/191aa557.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, offices](https://images.trvl-media.com/lodging/105000000/104500000/104497000/104496991/b90e3e32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/105000000/104500000/104497000/104496991/w905h683x60y0-49fbdf71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, offices](https://images.trvl-media.com/lodging/105000000/104500000/104497000/104496991/cfa1dab6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi

[](https://www.expedia.ca/Chicago-Hotels-Cozy-Family-Retreat-King-Beds.h104496991.Hotel-Information)

streamwood

10/10

Exceptional

(2 reviews)

"Was nice would recommend staying with you folks"

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

Richard W.

CA $192

CA $498 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Chicago-Hotels-Cozy-Family-Retreat-King-Beds.h104496991.Hotel-Information)

![Smart TV, books](https://images.trvl-media.com/lodging/121000000/120570000/120560100/120560017/0ca3e955.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120570000/120560100/120560017/817ec7df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120570000/120560100/120560017/2a1e5e9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120570000/120560100/120560017/a0ca263f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Schaumburg Modern 4BR Farmhouse w/ Private Master & Sleeps 9\. Families & groups

[](https://www.expedia.ca/Chicago-Hotels-When-Comfort-Meets-Convenience.h120560017.Hotel-Information)

Schaumburg

10/10

Exceptional

(7 reviews)

"Super comfy for families and the nicest host. "

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

Anonymous traveller

CA $432

CA $869 total

includes taxes & fees

Apr 8 - Apr 9

[](https://www.expedia.ca/Chicago-Hotels-When-Comfort-Meets-Convenience.h120560017.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=2026-04-18&endDate=2026-04-19&regionId=175751&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Winnetka%2C+Illinois%2C+United+States+of+America&regionId=175751&latLong=42.108082%2C-87.735893&adults=2&startDate=2026-07-03&d1=2026-07-03&endDate=2026-07-06&d2=2026-07-06&lodging=APART_HOTEL)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Winnetka%2C+Illinois%2C+United+States+of+America&regionId=175751&latLong=42.108082%2C-87.735893&adults=2&startDate=2026-07-03&d1=2026-07-03&endDate=2026-07-06&d2=2026-07-06&lodging=APARTMENT)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Winnetka%2C+Illinois%2C+United+States+of+America&regionId=175751&latLong=42.108082%2C-87.735893&adults=2&startDate=2026-07-03&d1=2026-07-03&endDate=2026-07-06&d2=2026-07-06&lodging=CONDO)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Winnetka%2C+Illinois%2C+United+States+of+America&regionId=175751&latLong=42.108082%2C-87.735893&adults=2&startDate=2026-07-03&d1=2026-07-03&endDate=2026-07-06&d2=2026-07-06&lodging=VACATION_HOME)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Winnetka%2C+Illinois%2C+United+States+of+America&regionId=175751&latLong=42.108082%2C-87.735893&adults=2&startDate=2026-07-03&d1=2026-07-03&endDate=2026-07-06&d2=2026-07-06&lodging=VILLA)

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## Top Winnetka Hotel Reviews

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

### Hotel Riu Plaza Chicago

8/10 Good

"Comfortable Room"

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

![Aloft Chicago Mag Mile](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/58ac280a_y.jpg)

### Aloft Chicago Mag Mile

8/10 Good

"Very live hotel, nice staff and clean. "

[](https://expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information)

![Hotel Felix River North/Magnificent Mile](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d891f039_y.jpg)

### Hotel Felix River North/Magnificent Mile

8/10 Good

"A quiet and comfortable place"

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

![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/a215cd17_y.jpg)

### Hilton Chicago/Magnificent Mile Suites

10/10 Excellent

"Location was great. Valet parking was very accommodating-- extremely helpful"

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

![River Hotel](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/5bec7925_y.jpg)

### River Hotel

10/10 Excellent

"Clean room as always Accessible to all main spots in Chicago "

[](https://expedia.ca/Chicago-Hotels-River-Hotel.h2675313.Hotel-Information)

![Hilton Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/a48bf16b_y.jpg)

### Hilton Chicago O'Hare Airport

10/10 Excellent

"I think you took advantage of people needing a place to stay when their flight was cancelled. The price was very inflated but we had very little choice about where we could stay. "

[](https://expedia.ca/Chicago-Hotels-Hilton-Chicago-OHare-Airport.h8058.Hotel-Information)

![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/24d28405_y.jpg)

### Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent

"Great experience "

[](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information)

![DoubleTree by Hilton Chicago - Magnificent Mile](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/757dbd3e_y.jpg)

### DoubleTree by Hilton Chicago - Magnificent Mile

10/10 Excellent

"Goods "

[](https://expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information)

![The Chicago Hotel Collection Ambassador Gold Coast](https://images.trvl-media.com/lodging/1000000/20000/17900/17809/b9c16475_y.jpg)

### The Chicago Hotel Collection Ambassador Gold Coast

4/10 Poor

"This was such a disappointing and underwhelming stay. There is zero soundproofing in the rooms, (constant door closing can be heard even over my white noise), housekeeping knocked at 8:20am to assess whether we were still in the room and my daughter was still sleeping, poor internet (WiFi was temperamental and TV was constantly losing signal), the terrace was closed/doors locked, pillows are thin and useless, beds are low to the ground, the carpet is stained and dingy, and I had to ask the front desk twice to review my profile bc I had been charged twice (was resolved). The food is such a loss here. If you’ve ever had food at a bowling alley, this is exactly what the line of food tastes like: I ordered beef empanadas and the margheritia pizza. The pizza tasted previously frozen and the empanadas give me Dollar General frozen food. Thank goodness I paid for “room only” and not the food/beverage package. The strong wins: location, and the bar scene/bartender. Valet was also exceptional. Only reason I didn’t give it 1 star. Do not recommend. The pictures do it way more justice than it deserves. If you’re seeking luxury, this is not it. And perhaps I was booked in a “cheap”/non-upgraded room, but this is not worth it."

[](https://expedia.ca/Chicago-Hotels-The-Chicago-Hotel-Collection-Ambassador-Gold-Coast.h17809.Hotel-Information)

## Find out more about Winnetka

## Winnetka Vacation Homes information

| Number of reviews | 388                |
| ----------------- | ------------------ |
| Accommodation     | 563 Vacation Homes |
| Lowest Price      | CA $274            |
| Highest Price     | CA $973            |

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