Compare Winnetka Villas

Start date: Check-in selected.
To Date
End date: Check-out

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Villas in Winnetka

HUGE! 3BR Private Home+Garage+360° Roof Deck+Hot Tub+EV+Sleeps 12

HUGE! 3BR Private Home+Garage+360° Roof Deck+Hot Tub+EV+Sleeps 12

Chicago IL
Guests of this villa enjoy features like a gym, a hot tub, and an arcade/game room. Other amenities at this family-friendly villa include laundry facilities, local meal delivery service, and barbecue grills.
Hot Tub
Kitchen
Charming Retreat in the Heart of Des Plaines by RedAwning

Charming Retreat in the Heart of Des Plaines by RedAwning

Des Plaines IL
At this villa, guests have access to a gym, laundry facilities, and barbecue grills.
▌360° City Skyline Chicago ▌

▌360° City Skyline Chicago ▌

Chicago IL
At this villa, guests have access to features like laundry facilities.
Washer
Dryer
Elegant Riverwoods Escape w/ Private Sauna!

Elegant Riverwoods Escape w/ Private Sauna!

3 out of 5
Deerfield IL
Guests staying at this villa enjoy free WiFi in public areas, an arcade/game room, and barbecue grills. You can put free offsite parking to good use if you drive.
Pet friendly
Free WiFi
Don't see what you're looking for?
See all available properties in Winnetka
View all properties
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.

Hotel Options in Winnetka

    Hilton Chicago

    Hilton Chicago

    720 S Michigan Ave Chicago IL
    $164 nightly
    The price is $192 total per night from Jan 16 to Jan 17
    $192 total
    Jan 16 - Jan 17
    Total with taxes and fees
    8.4/10 Very Good! (2,507 reviews)
    Palmer House a Hilton Hotel

    Palmer House a Hilton Hotel

    17 E Monroe St Chicago IL
    $168 nightly
    The price is $192 total per night from Jan 16 to Jan 17
    $192 total
    Jan 16 - Jan 17
    Total with taxes and fees
    8.4/10 Very Good! (2,223 reviews)
    Hilton Chicago/Magnificent Mile Suites

    Hilton Chicago/Magnificent Mile Suites

    198 E Delaware Pl Chicago IL
    $89 nightly
    The price is $105 total per night from Jan 18 to Jan 19
    $105 total
    Jan 18 - Jan 19
    Total with taxes and fees
    8.8/10 Excellent! (3,668 reviews)

Luxury Villas

Book luxury villas in Winnetka
There are plenty of ways to up your vacation game, but one of the best is by staying in a luxury villa in Winnetka. Villas, with their thoughtful layout and elegant décor, let you travel in style. They come in a variety of sizes and offer a great experience, whether you’re traveling on your own or with a group of friends. Orbitz has fantastic deals on villas in Winnetka, so book one now. You’ll feel like a million bucks before you even check in.

Spacious luxury villas in Winnetka
You won’t have a problem finding your own space in Winnetka. If you’re traveling in a group, go for a three-bedroom or larger villa; separate bedrooms can make it that much easier to keep the peace, especially when you’re all staying in one house. You can also explore Winnetka on your own and use a one-bedroom villa as your home base.

A top-end villa experience in Winnetka rivals that of a luxury resort. Float in a swimming pool with an elaborate mosaic bottom, work out in your own gym, and let the daily housekeeping staff clean up after you while a private chef whips up one delicious meal after another. This is the life!

Winnetka Villas essential information

Accommodation
5 Villas
Lowest Price
$105
Highest Price
$192
Popular accommodation
HUGE! 3BR Private Home+Garage+360° Roof Deck+Hot Tub+EV+Sleeps 12, Charming Retreat in the Heart of Des Plaines by RedAwning, ▌360° City Skyline Chicago ▌ , Elegant Riverwoods Escape w/ Private Sauna!