Winnetka Holiday Rentals from €73: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Winnetka has to offer?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line : This holiday home rental outside of Winnetka is located in the city centre, and has a balcony, a BBQ and air conditioning to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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Our top choices for Winnetka holiday rentals

A spacious hotel lobby with a high ceiling, chandeliers, and a bar area.

1. The Gem Museum Suites

Downtown Evanston

Archita

includes taxes & fees

29 Oct - 30 Oct

A patio area with outdoor seating and solar-powered lights.

2. Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More

South Evanston

Colleen B.

A building with a stone facade and a large window displaying the text 'LAUNDRY MAT'.

3. King Bed Non-Smoking

Chicago

Anonymous traveller

includes taxes & fees

4 Oct - 5 Oct

A hotel room with a bed, two pillows, a nightstand with a lamp, and two abstract paintings on the wall.

4. Chic Studio - In Downtown Highland Park, by Metra

Highland Park

Deborah

includes taxes & fees

11 Oct - 12 Oct

A modern interior with a dining area, seating, a fireplace, and large windows offering a view of buildings outside.

5. "Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

Downtown Evanston

Surath G.

includes taxes & fees

11 Oct - 12 Oct

A modern bedroom with a bed, a sofa, and a hanging plant.

6. Cozy studio in Andersonville Chicago

Edgewater

Katie K.

includes taxes & fees

26 Oct - 27 Oct

7. Chicago's Hidden Treasure "Evanston, IL" Urban Luxury with comfort

Downtown Evanston

Robin M.

includes taxes & fees

29 Sept - 30 Sept

A modern house with a covered porch, large windows, and a well-maintained garden with various plants and flowers.

8. Master qtr close to nature & easy urban facilities

Riverwoods

Chris F.

includes taxes & fees

30 Sept - 1 Oct

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Top Winnetka Hotel Reviews

River Hotel

10/10 Excellent

"Perfect location"

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

8/10 Good

"The staff are definitely the highlight of this hotel. The interior/lobby is BEAUTIFUL and the bar in the lobby was amazing, drinks were very good. Just stayed 1 night, they upgraded my room for free which was very nice but once I got into the room I could immediately tell it was a MUCH older hotel. The decor was outdated, there was also just a bed and a desk chair in the room lol nothing else. Couldn’t sit anywhere that wasn’t the bed…bathroom was okay too. Towels had some stains on them. Other than that it was a decent stay. I’d probably book somewhere else next time just because it’s not as modern as it seemed to be online but if you like the older style hotels definitely check this one out."

Find out more about Winnetka

Everything you need to know about Winnetka holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winnetka holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winnetka holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winnetka holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winnetka holiday rentals we have selected for you start as low as €73 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winnetka rentals

At Expedia, we put the best Winnetka holiday 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 holiday.

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.

Frequently asked questions

Can I find holiday rentals in Winnetka?

Yes, there are holiday rentals close to the most popular sights in Winnetka, or you can select a more secluded option if you're looking for a relaxing stay. Winnetka is known for its shopping and forests. Make sure you have time to check out the sporting events and restaurants during your trip.

What are some of the best holiday rentals that Winnetka has to offer?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This holiday home rental outside of Winnetka is located in the city centre, and has a balcony, a BBQ and air conditioning to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What can I see and do in Winnetka?

Lake Michigan and Maple Street Beach are a couple of lovely local spots to get outside and enjoy nature. While in the area, you can also visit popular places such as Wrigley Field and Navy Pier.

What are holiday rentals like in Winnetka?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winnetka. Holiday rentals offer extras like laundry facilities and kitchens so you'll have everything you need. If you're concerned about a clean environment, a holiday rental can provide a sense of safety away from shared hotel lifts and bustling concierge desks while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for a family trip or a small group gathering.

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