Winnetka vacation rentals

We found 461 vacation rentals — enter your dates for availability

your current months are April, 2024 and May, 2024.
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Scroll through and select from vacation rentals in Winnetka to find one that's perfect for your trip. Vacation rentals offer the amenities you expect for your stay with friends, family, or just your pet, like cable TV and a washer and dryer. What you'll find is a rental for everyone's needs, including places that are non-smoking or accessible.

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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-sees in the area. A vacation rental can help make your stay complete. Many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Winnetka

Are you searching for things to do in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Winnetka a one-of-a-kind vacation spot. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Home Alone House (0.2 mi / 0.3 km)
  • The Glen Club (4.9 mi / 7.8 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)
  • Topgolf (16.7 mi / 26.9 km)

Exploring the natural landscape of Winnetka

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Winnetka is a great place to get outside. These are some of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

  • Grant Park (17.3 mi / 27.8 km)
  • Millennium Park (16.6 mi / 26.7 km)
  • Chicago Botanic Garden (3.8 mi / 6.1 km)
  • Ravinia Park (4 mi / 6.5 km)
  • Portage Park (10.7 mi / 17.2 km)
  • Montrose Beach (11 mi / 17.7 km)

Transportation to and around Winnetka

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

If you're traveling 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 vacation rental?

If you're thinking about a trip to Winnetka, Northfield is one of the most desirable neighborhoods 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 vacation rental accommodation in Winnetka?

Based on our research, houses are the most sought-after vacation property type in Winnetka. But as you'd expect, everyone's idea of an epic stay is bound to be different. Vrbo has vacation 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 vacation rental in Winnetka?

The average price for a vacation 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 vacation rental. Click on your Winnetka travel dates to view your options on Vrbo. Can't live without a private pool? Use our filters to select the features and amenities you need.

Are there pet-friendly vacation rentals in Winnetka?

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

What are popular rental amenities in Winnetka?

When it comes to rental amenities that people look for in Winnetka, a garden, a swimming pool and a barbecue grill rank highest. With Vrbo vacation rentals, 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 vacation rentals in Winnetka that welcome kids?

Winnetka has two family-friendly vacation rentals. 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 vacation rentals with WiFi in Winnetka?

You can choose from two vacation rentals 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 Vrbo.

How can I find vacation rentals with air conditioning in Winnetka?

Winnetka has two vacation rentals where you can kick back in air-conditioned comfort. To find a property on Vrbo 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 vacation rental in Winnetka?

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

How long can I rent a vacation rental in Winnetka for?

The amount of time you can book a Winnetka vacation 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 vacation homes might also offer discounted weekly or monthly prices, so you can stick around for longer for less.

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