Title: Winnetka Vacation Rentals from $130: Search Short-Term Rentals | Expedia.com

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

![Lodging Image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

## Check prices for these dates

In two weeks

[Feb 27 - Mar 1](https://www.expedia.com/Hotel-Search?regionId=175751&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=175751&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=175751&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=175751&startDate=2026-06-05&endDate=2026-06-07&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 rentals

![Indoor pool](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/58291697.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/ccaab668.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Apartment, 1 Bedroom | Private kitchen | Oven, stovetop, dishwasher, coffee/tea maker](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/f6d9d5c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Apartment, 2 Bedrooms | Private kitchen | Oven, stovetop, dishwasher, coffee/tea maker](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/83f39cf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sentral Michigan Avenue

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

Downtown Chicago

9.2/10

Wonderful

(1,071 reviews)

"Best full kitchen multi-room family lodging"

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

Lee

$135 nightly

$158 total

Feb 10 - Feb 11

Total with taxes and fees

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

![Dining room](https://images.trvl-media.com/lodging/47000000/46240000/46231100/46231022/264e98f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![49-inch Smart TV with digital channels, TV, streaming services](https://images.trvl-media.com/lodging/47000000/46240000/46231100/46231022/5915e3d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/47000000/46240000/46231100/46231022/a150e313.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Studio, 1 Queen Bed with Sofa bed, Non Smoking (Self Check-in with Virtual Front Desk) | Premium bedding, memory foam beds, individually decorated](https://images.trvl-media.com/lodging/47000000/46240000/46231100/46231022/5de126ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kasa Magnificent Mile Chicago

[](https://www.expedia.com/Chicago-Hotels-Kasa-Chicago-River-North-Apartments.h46231022.Hotel-Information)

Downtown Chicago

9.4/10

Exceptional

(690 reviews)

"Perfect location and very clean! "

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

Latoya

$188 nightly

$220 total

Feb 10 - Feb 11

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Kasa-Chicago-River-North-Apartments.h46231022.Hotel-Information)

![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8c061e2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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)

![Premium bedding, pillowtop beds, in-room safe, individually decorated](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/4a3a770c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, 1 Twin Bed, City View | Living area | Flat-screen TV](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/f7ca0ea3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Level Chicago – Old Town

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

Downtown Chicago

9.0/10

Wonderful

(423 reviews)

"Clean, nice amenities and great staff."

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

Sydnee

$214 nightly

$252 total

Feb 10 - Feb 11

Total with taxes and fees

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

![Living area](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/3e1fd538.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/6dcfa9e1.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)

![Living area](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/3935f43c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wrigleyville Suites

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

Lakeview

9.2/10

Wonderful

(29 reviews)

"Nice place "

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

Barry

$132 nightly

$155 total

Feb 10 - Feb 11

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/89000000/88910000/88902400/88902334/c487cf4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/89000000/88910000/88902400/88902334/faa6dc46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/89000000/88910000/88902400/88902334/52817ea9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio | Private kitchen | Fridge, oven, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/89000000/88910000/88902400/88902334/e09cfe7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chicago Third Floor Studio by 747 Lofts

[](https://www.expedia.com/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)

West Town

9.8/10

Exceptional

(7 reviews)

"Clean, easy to check in, all the household items you’d expect"

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

Jason

$287 nightly

$337 total

Feb 15 - Feb 16

Total with taxes and fees

[](https://www.expedia.com/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)

![Breakfast, lunch, dinner served; Greek cuisine ](https://images.trvl-media.com/lodging/104000000/103470000/103465500/103465448/424c972a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/104000000/103470000/103465500/103465448/9897f375.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Gym](https://images.trvl-media.com/lodging/104000000/103470000/103465500/103465448/ee528550.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Full-size fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/104000000/103470000/103465500/103465448/c54d2fb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Gem Museum Suites

[](https://www.expedia.com/Chicago-Hotels-The-Gem-Museum-Suites.h103465448.Hotel-Information)

Downtown Evanston

9.4/10

Exceptional

(104 reviews)

"This is a fantastic hotel with super friendly staff"

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

German

$182 nightly

$208 total

Feb 16 - Feb 17

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-The-Gem-Museum-Suites.h103465448.Hotel-Information)

![Apartment, Private Bathroom | Lounge](https://images.trvl-media.com/lodging/76000000/75610000/75609600/75609586/75db7b4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, Private Bathroom | Interior](https://images.trvl-media.com/lodging/76000000/75610000/75609600/75609586/d23bf6a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, Private Bathroom | Terrace/patio](https://images.trvl-media.com/lodging/76000000/75610000/75609600/75609586/2e2b5c00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/76000000/75610000/75609600/75609586/a3594234.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### At Home in Oak Park

[](https://www.expedia.com/Chicago-Hotels-Home-In-Oak-Park.h75609586.Hotel-Information)

Oak Park

9.4/10

Exceptional

(9 reviews)

"Great location in Oak Park- walkable, wondering area for restaurants and strolling through the beautiful neighborhoods."

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

Kathryn

$224 nightly

$257 total

Feb 10 - Feb 11

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Home-In-Oak-Park.h75609586.Hotel-Information)

![Exclusive Apartment, Private Bathroom, Garden View (1st Floor) | Lounge](https://images.trvl-media.com/lodging/89000000/88180000/88173500/88173402/8abcd27a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exclusive Apartment, Private Bathroom, Garden View (1st Floor) | Shared kitchen](https://images.trvl-media.com/lodging/89000000/88180000/88173500/88173402/cf45226f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exclusive Apartment, Private Bathroom, Garden View (1st Floor) | Interior](https://images.trvl-media.com/lodging/89000000/88180000/88173500/88173402/7547fb3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/89000000/88180000/88173500/88173402/a6832f09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic Oak Park Home

[](https://www.expedia.com/Chicago-Hotels-Historic-Oak-Park-Home.h88173402.Hotel-Information)

Oak Park

10/10

Exceptional

(5 reviews)

"Wanted a house in oak park and this was such a pleasant, comfortable and convenient place. Really comfortable beds too. Even a lovely piano. "

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

judith

$217 nightly

$248 total

Feb 10 - Feb 11

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Historic-Oak-Park-Home.h88173402.Hotel-Information)

![Lounge](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/0480d64e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, open 10:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/88e54d1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Signature Apartment, 1 King Bed with Sofa bed, Pool Access (Self Check-in with Virtual Front Desk) | Living area | 55-inch flat-screen TV with digital channels, TV](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/2969f0ad.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

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

Downtown Chicago

9.6/10

Exceptional

(183 reviews)

"Awesome stay "

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

Sally

$229 nightly

$269 total

Feb 27 - Feb 28

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/89000000/88870000/88870000/88869909/47ef186d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/89000000/88870000/88870000/88869909/63b4bd8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/89000000/88870000/88870000/88869909/f020c8c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen | Fridge, oven, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/89000000/88870000/88870000/88869909/1d5178cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ground Floor Studios in Chicago by 747 Lofts

[](https://www.expedia.com/Chicago-Hotels-Stylish-Studio-Offers-The-Perfect-Location-For-Your-Windy-City-Wanderings-747-Lofts-Cabin-101-Hotel-Room.h88869909.Hotel-Information)

West Town

9.0/10

Wonderful

(21 reviews)

"The stay lacked in shelf space as well as other amenities that could be useful. "

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

Zugeily

$171 nightly

$200 total

Feb 12 - Feb 13

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Stylish-Studio-Offers-The-Perfect-Location-For-Your-Windy-City-Wanderings-747-Lofts-Cabin-101-Hotel-Room.h88869909.Hotel-Information)

![Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Exterior](https://images.trvl-media.com/lodging/95000000/94680000/94670100/94670079/9b9f65df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Exterior](https://images.trvl-media.com/lodging/95000000/94680000/94670100/94670079/3a1a2525.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exclusive Room, Private Bathroom, Garden View (2nd Floor) | 4 bedrooms](https://images.trvl-media.com/lodging/95000000/94680000/94670100/94670079/5beac5cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Restaurant](https://images.trvl-media.com/lodging/95000000/94680000/94670100/94670079/de6cdd22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic Oak Park Residence

[](https://www.expedia.com/Chicago-Hotels-Historic-Oak-Park-Residence.h94670079.Hotel-Information)

Oak Park

9.6/10

Exceptional

(12 reviews)

"Absolutely awesome "

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

Erik

$217 nightly

$248 total

Feb 10 - Feb 11

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-Historic-Oak-Park-Residence.h94670079.Hotel-Information)

![Design Apartment, Private Bathroom (The Oak Park Loft) | 2 bedrooms](https://images.trvl-media.com/lodging/108000000/107630000/107622700/107622605/dfb80f4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Design Apartment, Private Bathroom (The Oak Park Loft) | 2 bedrooms](https://images.trvl-media.com/lodging/108000000/107630000/107622700/107622605/023c5e28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107630000/107622700/107622605/167883c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Design Apartment, Private Bathroom (The Oak Park Loft) | 2 bedrooms](https://images.trvl-media.com/lodging/108000000/107630000/107622700/107622605/515455d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Oak Park Loft

[](https://www.expedia.com/Chicago-Hotels-The-Oak-Park-Loft.h107622605.Hotel-Information)

Oak Park

10/10

Exceptional

(5 reviews)

"Good location, nice neighborhood, restaurants close"

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

Linda

$217 nightly

$248 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/Chicago-Hotels-The-Oak-Park-Loft.h107622605.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.

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## Find vacation rentals that suit your style

Aparthotels

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Apartments

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Condos

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Private vacation homes

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Villas

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Cottages

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Residences

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## Top Winnetka Hotel Reviews

![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg)

### Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent

"Amenities"

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

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

### Hotel Riu Plaza Chicago

10/10 Excellent

"The breakfasts, how clean it was, and its convenience. I would recommend 10/10"

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

![Courtyard by Marriott Chicago Magnificent Mile](https://images.trvl-media.com/lodging/1000000/990000/982600/982517/529d8be8_y.jpg)

### Courtyard by Marriott Chicago Magnificent Mile

10/10 Excellent

"Room was clean. Staff was courteous. "

[](https://expedia.com/Chicago-Hotels-Courtyard-By-Marriott-Chicago-Magnificent-Mile.h982517.Hotel-Information)

![Hyatt Regency Chicago](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg)

### Hyatt Regency Chicago

10/10 Excellent

"Yes"

[](https://expedia.com/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information)

![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982_y.jpg)

### Eurostars Magnificent Mile

10/10 Excellent

"Staff team was friendly and professional and also really helpful "

[](https://expedia.com/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information)

![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg)

### Hilton Chicago

10/10 Excellent

"Good"

[](https://expedia.com/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information)

![The Royal Sonesta Chicago Downtown](https://images.trvl-media.com/lodging/1000000/20000/17600/17543/696a55e6_y.jpg)

### The Royal Sonesta Chicago Downtown

10/10 Excellent

"Good Staff and very clean room"

[](https://expedia.com/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.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

"Great staff, room spotless, great price."

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

![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/74c2f40d_y.jpg)

### LondonHouse Chicago, Curio Collection by Hilton

10/10 Excellent

"Nice room and friendly staff. Bar and restaurant were both great as well"

[](https://expedia.com/Chicago-Hotels-LondonHouse-Chicago.h12786616.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, apartments, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Winnetka in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $130 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.com
- All accommodation types in Winnetka

### Trending destinations on Expedia.com

- [Destin Vacation Rentals ](https://www.expedia.com/Destin-Vacation-Rentals.d6906.Travel-Guide-VacationRentals)
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- [Hilton Head Vacation Rentals ](https://www.expedia.com/Hilton-Head-Island-Vacation-Rentals.d601684.Travel-Guide-VacationRentals)
- [Gulf Shores Vacation Rentals ](https://www.expedia.com/Gulf-Shores-Vacation-Rentals.d603078.Travel-Guide-VacationRentals)
- [Key West Vacation Rentals ](https://www.expedia.com/Key-West-Vacation-Rentals.d1187.Travel-Guide-VacationRentals)
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- [Maui Vacation Rentals ](https://www.expedia.com/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals)
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- [Pigeon Forge Vacation Rentals ](https://www.expedia.com/Pigeon-Forge-Vacation-Rentals.d8264.Travel-Guide-VacationRentals)
- [Ocean City Vacation Rentals ](https://www.expedia.com/Ocean-City-Vacation-Rentals.d9151.Travel-Guide-VacationRentals)
- [Outer Banks Vacation Rentals ](https://www.expedia.com/Outer-Banks-Vacation-Rentals.d602135.Travel-Guide-VacationRentals)
- [San Diego Vacation Rentals ](https://www.expedia.com/San-Diego-Vacation-Rentals.d3073.Travel-Guide-VacationRentals)
- [Siesta Key Vacation Rentals ](https://www.expedia.com/Siesta-Key-Vacation-Rentals.d6881.Travel-Guide-VacationRentals)
- [Galveston Vacation Rentals ](https://www.expedia.com/Galveston-Vacation-Rentals.d1341.Travel-Guide-VacationRentals)
- [Clearwater Beach Vacation Rentals ](https://www.expedia.com/Clearwater-Beach-Vacation-Rentals.d10759.Travel-Guide-VacationRentals)
- [Palm Springs Vacation Rentals ](https://www.expedia.com/Palm-Springs-Vacation-Rentals.d180676.Travel-Guide-VacationRentals)
- [Florida Keys Vacation Rentals ](https://www.expedia.com/Florida-Keys-Vacation-Rentals.d6023765.Travel-Guide-VacationRentals)
- [Lake Tahoe Vacation Rentals ](https://www.expedia.com/South-Lake-Tahoe-Vacation-Rentals.d10150.Travel-Guide-VacationRentals)
- [Lake of the Ozarks Vacation Rentals ](https://www.expedia.com/Lake-Ozark-Vacation-Rentals.d177772.Travel-Guide-VacationRentals)
- [Florida Vacation Rentals ](https://www.expedia.com/Destinations-In-Florida.d211.Vacation-Rental-Destinations)
- [Hawaii Vacation Rentals ](https://www.expedia.com/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations)
- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

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

## Frequently asked questions

### Can I find vacation rentals in Winnetka?

### What are some of the best vacation rentals in Winnetka?

### What can I see and do in Winnetka?

### What are vacation rentals like in Winnetka?

### Expedia's Latest Trends

Hotels

- [Hotels in Lombard](https://expedia.com/Lombard-Hotels.d8393.Travel-Guide-Hotels)
- [Hotels in Cicero](https://expedia.com/Cicero-Hotels.d89615.Travel-Guide-Hotels)
- [Hotels in Carol Stream](https://expedia.com/Carol-Stream-Hotels.d6500.Travel-Guide-Hotels)
- [Hotels in Vernon Hills](https://expedia.com/Vernon-Hills-Hotels.d6371.Travel-Guide-Hotels)
- [Hotels in Northbrook](https://expedia.com/Northbrook-Hotels.d9142.Travel-Guide-Hotels)
- [Hotels in Skokie](https://expedia.com/Skokie-Hotels.d6903.Travel-Guide-Hotels)
- [Hotels in Gurnee](https://expedia.com/Gurnee-Hotels.d8240.Travel-Guide-Hotels)
- [Hotels in Downers Grove](https://expedia.com/Downers-Grove-Hotels.d181500.Travel-Guide-Hotels)
- [Hotels in Schaumburg](https://expedia.com/Schaumburg-Hotels.d8107.Travel-Guide-Hotels)
- [Hotels in Arlington Heights](https://expedia.com/Arlington-Heights-Hotels.d6231.Travel-Guide-Hotels)
- [Hotels in Des Plaines](https://expedia.com/Des-Plaines-Hotels.d7863.Travel-Guide-Hotels)
- [Hotels in Waukegan](https://expedia.com/Waukegan-Hotels.d10174.Travel-Guide-Hotels)
- [Hotels in Hoffman Estates](https://expedia.com/Hoffman-Estates-Hotels.d7602.Travel-Guide-Hotels)
- [Hotels in Rosemont](https://expedia.com/Rosemont-Hotels.d7581.Travel-Guide-Hotels)
- [Hotels in Oak Brook](https://expedia.com/Oak-Brook-Hotels.d9218.Travel-Guide-Hotels)
- [Hotels in Glenview](https://expedia.com/Glenview-Hotels.d8006.Travel-Guide-Hotels)
- [Hotels in Oak Lawn](https://expedia.com/Oak-Lawn-Hotels.d9227.Travel-Guide-Hotels)
- [Hotels in Evanston](https://expedia.com/Evanston-Hotels.d8049.Travel-Guide-Hotels)
- [Hotels in Naperville](https://expedia.com/Naperville-Hotels.d9009.Travel-Guide-Hotels)
- [Hotels in Wheaton](https://expedia.com/Wheaton-Hotels.d7599.Travel-Guide-Hotels)
- [Hotels in Bolingbrook](https://expedia.com/Bolingbrook-Hotels.d55064.Travel-Guide-Hotels)
- [Hotels in Elmhurst](https://expedia.com/Elmhurst-Hotels.d7836.Travel-Guide-Hotels)
- [Hotels in Orland Park](https://expedia.com/Orland-Park-Hotels.d9270.Travel-Guide-Hotels)
- [Hotels in Oak Park](https://expedia.com/Oak-Park-Hotels.d9228.Travel-Guide-Hotels)

Cars

- [Car rentals in Naperville](https://expedia.com/Car-Rentals-In-Naperville.d9009.Car-Rental-Guide)
- [Car rentals in Des Plaines](https://expedia.com/Car-Rentals-In-Des-Plaines.d7863.Car-Rental-Guide)
- [Car rentals in Schaumburg](https://expedia.com/Car-Rentals-In-Schaumburg.d8107.Car-Rental-Guide)
- [Car rentals in Bolingbrook](https://expedia.com/Car-Rentals-In-Bolingbrook.d55064.Car-Rental-Guide)
- [Car rentals in Orland Park](https://expedia.com/Car-Rentals-In-Orland-Park.d9270.Car-Rental-Guide)

Activities

- [Things to do in Schaumburg](https://expedia.com/Things-To-Do-In-Schaumburg.d8107.Travel-Guide-Activities)