Winnetka holiday lettings

We found 571 holiday rentals — enter your dates for availability

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.

Find spaces that suit your style

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  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

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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-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)
  • Northbrook Sports Complex (5.9 mi / 9.4 km)
  • Chevy Chase Country Club (10 mi / 16.1 km)
  • The Dome at the Parkway Bank Sports Complex (11.3 mi / 18.1 km)
  • Lincoln Park Zoo (14 mi / 22.5 km)
  • Dave & Buster's (15.3 mi / 24.6 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)
  • North Shore Beach Park (8.2 mi / 13.3 km)
  • Kathy Osterman Beach (9.4 mi / 15.2 km)
  • Portage Park (10.7 mi / 17.2 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 rental?
When considering a holiday rental in Winnetka, Illinois, the best area to stay is the picturesque neighbourhood near the lakefront. This region not only offers stunning views and a serene atmosphere but also provides convenient access to some of the area's top attractions. One highlight is the beautiful Winnetka Beach, which is great for leisurely strolls and enjoying the outdoors. Additionally, the nearby historic Village Green is a lovely spot for picnics and community events, making it a vibrant focal point for both locals and visitors.

In terms of accommodation, the neighbourhood features a range of properties that cater to various preferences, from charming cottages to more spacious family homes. Staying in this area allows you to immerse yourself in the local culture while enjoying the tranquillity of the lakeside environment.
How much does it cost to rent a holiday home in Winnetka?
Prices for holiday rentals in Winnetka vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Winnetka to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Winnetka holiday house rentals?
You can find great discounts on house rentals in Winnetka on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I find long-stay holiday rentals in Winnetka?
A long-stay holiday rental in Winnetka is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there any Winnetka holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Winnetka with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
When is the best time to visit Winnetka for a holiday rental?
The best time to visit Winnetka for a holiday rental is during the peak season of June to August, with July being the most popular month. This vibrant summer period attracts travellers, who come to enjoy the beautiful beaches along Lake Michigan and partake in numerous outdoor activities.

During these months, you can expect pleasant temperatures ranging from the mid-teens to low 30s Celsius, great for sunbathing, picnicking, or simply strolling along the picturesque shoreline. The lively option is complemented by local events and festivals, allowing visitors to immerse themselves in the community spirit.

For those considering a more budget-friendly option, October offers a lovely alternative. The fall season brings cooler temperatures, typically ranging from 5 to 15 degrees Celsius, and showcases stunning autumn foliage. It's a quieter time to explore the charming streets of Winnetka, with fewer crowds, making it ideal for leisurely walks and enjoying the seasonal scenery.
How early should I book a Winnetka holiday rental?
Book your Winnetka holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Winnetka?
In Winnetka, visitors can enjoy a variety of attractions that showcase the charm of this affluent suburb. One of the highlights is the picturesque Winnetka Beach, which offers sandy shores along Lake Michigan, superb for swimming and sunbathing during the warmer months. The beach area features scenic walking paths and picnic spots, making it a great place for families and outdoor enthusiasts.

The historic downtown area is another attraction, where visitors can explore boutique shops, cafes, and restaurants, all housed in charming architectural styles. Nearby, the Winnetka Community House often hosts various events, including art exhibits and performances, contributing to the local cultural scene.

For nature lovers, the Skokie Lagoons, just a short drive away, provide opportunities for hiking, biking, and birdwatching. Additionally, the nearby Crow Island Woods offers wooded trails and open spaces, ideal for leisurely walks and enjoying the natural beauty of the area.
Can I change or cancel my Winnetka home rental booking on Vrbo?
To find Winnetka holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Winnetka holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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