Winnetka holiday homes, IL, USA: holiday houses & more

Scroll through and select from holiday rentals in Winnetka to find one that's perfect for your trip. Holiday rentals offer the amenities that you expect for your stay with friends, family or just your pet, such as a fireplace and garden. What you'll find is a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Winnetka

Showing deals for:18 Jul - 25 Jul

Exceptional

(80 reviews)

SPACIOUS 3BD - 2BA DUPLEX WITH FAMILY ROOM, KING BED-LAUNDRY ROOM & FIREPLACE

Chicago, IL

8% off

NZ$1,070 per night

includes taxes & fees

Exceptional

(5 reviews)

The Executive Residence -Luxury 5 Br 4.5 Ba- 0.8 acre- 5400 sqft- Lake Community

Prospect Heights, IL

8% off

NZ$1,429 per night

includes taxes & fees

Private bedroom. Bright and sunny. Ample closet space. Extra towels.

Exceptional

(11 reviews)

Newly Renovated 1 BR in Art Deco Architectural Gem, Steps to L & Free Parking

Chicago, IL

8% off

NZ$789 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Winnetka

Warm and Cheerful 3 Bedroom Winnetka Townhouse

Sleeps 6 · 3 bedrooms · 1+ bathroom

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Take in the lush beauty of Winnetka

The forests and other outdoor surroundings create an inviting atmosphere in Winnetka. Renowned for its shopping, sporting events and restaurants, this city welcomes all visitors. Wrigley Field and Naval Base Great Lakes are just a couple of the must-see attractions in the area. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Winnetka

Are you hoping to find things to do while you're in the area? Venture out of your cosy holiday rental and check out everything that makes Winnetka a fun place to get away to. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

The Glen Club (4.9 mi / 7.8 km)
Chevy Chase Country Club (10 mi / 16.1 km)
Arlington International Racecourse (13.9 mi / 22.4 km)
Lincoln Park Zoo (14 mi / 22.5 km)
LEGOLAND® Discovery Center (16 mi / 25.7 km)
Pirates Cove Childrens Theme Park (16 mi / 25.8 km)

Exploring the natural landscape of Winnetka

Whether you're an adventurous traveller or just want to appreciate the scenery, Winnetka is a great place to get out in nature. These are some of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

Millennium Park (16.6 mi / 26.7 km)
Grant Park (17.3 mi / 27.8 km)
Chicago Botanic Garden (3.8 mi / 6.1 km)
Portage Park (10.7 mi / 17.2 km)
Montrose Beach (11 mi / 17.7 km)
Lincoln Park (12.3 mi / 19.8 km)

Transport to and around Winnetka

The nearest airport is in Chicago, IL (PWK-Chicago Executive), located 8.4 mi (13.5 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Chicago O'Hare International Airport (ORD), which is 12.5 mi (20.2 km) away.

If you're travelling by train, make your way to Winnetka Station or Winnetka Indian Hill Station and explore the city from there.

Frequently asked questions

What is the best area to stay in Winnetka when booking a holiday home?

If you’re thinking about a trip to Winnetka, Northfield is one of the most desirable neighbourhoods to stay. Whether you go for a condo, cottage or other property style, you’ll always have the entire place to yourself.

What is the most popular type of holiday home accommodation in Winnetka?

Based on our research, houses are the most sought-after holiday property type in Winnetka. But as you’d expect, everyone’s idea of an epic stay is bound to be different. Bookabach has holiday homes with every shape, size and budget in mind, and we’ll help you find the perfect fit for you.

How much does it cost to rent a holiday home in Winnetka?

The average price for a holiday home in Winnetka depends on several factors, including length of stay, property type and season. Whether you’re in search of a villa with space for extended family or an apartment for just you and the kids, just enter your travel dates to view stays with exceptional value.

How much does it cost to rent a beach house in Winnetka?

When you travel and the size and style of the property will influence how much you’ll pay for your beachside holiday home. Click on your Winnetka travel dates to view your options on Bookabach. Can’t live without a private pool? Use our filters to select the features and amenities you need.

Are there pet-friendly holiday homes in Winnetka?

Pack a travel bag and a bone for your pooch because Winnetka has two holiday homes that welcome pets with open arms. Let your furriest pal join in on the family trip at one of our pet-friendly holiday homes on Bookabach. Simply enter your travel dates and destination, then check our “Pets allowed” filter box.

What are popular home amenities in Winnetka?

When it comes to home amenities that people look for in Winnetka, a garden, a swimming pool and a barbecue grill rank highest. With Bookabach holiday homes, there are choices to suit your taste and style, whether you’re going on a trip with your partner, your family or even pets.

Are there holiday homes in Winnetka that welcome kids?

Winnetka has two family-friendly holiday homes. And booking a stay that welcomes kiddos is super easy with our “Properties good for families” filter. On top of having the entire place to yourselves, you’ll enjoy access to conveniences and perks such as dining rooms, full kitchens and yards.

What are the top attractions for families in Winnetka?

Keep the kids happy at these fantastic family-friendly attractions in Winnetka:

Kohl Childrens Museum
North Shore Beach Park
Wagner Farm

Are there holiday homes with WiFi in Winnetka?

You can choose from two holiday homes with WiFi in Winnetka. If you’d like to disconnect from daily life on your break, but still want to be connected to the web, these properties are for you. Narrow your search by applying the WiFi filter on Bookabach.

How can I find holiday homes with air conditioning in Winnetka?

Winnetka has two holiday homes where you can kick back in air-conditioned comfort. To find a property on Bookabach that offers this amenity, enter your travel dates and use the filters to select the “air conditioning” box.

How old do you have to be to rent a holiday home in Winnetka?

The minimum age allowed can differ between properties on Bookabach, so double-check the rules of the holiday home in Winnetka you want. But usually, it’s 16, 18 or 21.

How long can I rent a holiday home in Winnetka for?

The amount of time you can book a Winnetka holiday home for is up to the property. Simply enter your travel dates to find options offering extended stays. They come with all you require to make your extended break more enjoyable and comfortable, such as kitchens and laundries. Some holiday homes might also offer discounted weekly or monthly prices, so you can stick around for longer for less.