Are there any 5-star vacation rentals in Winnetka?

Although you won't find any 5-star vacation rentals in Winnetka on our site, we have a range of stays that promise a memorable getaway. Find one that matches your style by searching our vacation rentals in Winnetka .

The Best 5 Star Hotels in Winnetka, IL from $128

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Our top choices for Winnetka 5-star hotels

Suite, 2 Bedrooms, Terrace (Lakeshore) | Lake view

Four Seasons Hotel Chicago

Downtown Chicago

Sean

$410 nightly

Mar 15 - Mar 16

Total with taxes and fees

The Langham, Chicago

Downtown Chicago

Hussein

$457 nightly

Mar 26 - Mar 27

Total with taxes and fees

Trump International Hotel & Tower Chicago

Downtown Chicago

Julie

$371 nightly

Mar 11 - Mar 12

Total with taxes and fees

The Peninsula Chicago

Downtown Chicago

Maysa

$473 nightly

Mar 25 - Mar 26

Total with taxes and fees

Breakfast, lunch, dinner served; American cuisine, alfresco dining

Park Hyatt Chicago

Downtown Chicago

Gaybrielle

$412 nightly

Mar 29 - Mar 30

Total with taxes and fees

Waldorf Astoria Chicago

Downtown Chicago

Glenn

$410 nightly

Mar 22 - Mar 23

Total with taxes and fees

The Ritz-Carlton, Chicago

Downtown Chicago

Curtis

$396 nightly

Mar 15 - Mar 16

Total with taxes and fees

Designer toiletries, hair dryer, bathrobes, towels

Nobu Hotel Chicago

Downtown Chicago

Paulo

$286 nightly

Mar 5 - Mar 6

Total with taxes and fees

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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Winnetka.

Embassy Suites by Hilton Chicago Downtown River North

600 N State St Chicago IL

$120 nightly

$141 total

Mar 5 - Mar 6

Total with taxes and fees

8.6/10 Excellent! (5,713 reviews)

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Pool Spa Hot tub Breakfast included Waterpark

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.

Learn more about Winnetka

Elegant North Shore homes line the streets near Lake Michigan beaches where locals picnic during summer festivals. Explore the historic Crow Island School's architecture or catch a show at the Winnetka Community House theater.

See all hotels in Winnetka

Stinson Memorial Library Anna Illinois Listed on the National Register Funded by Anna businessman Robert Burns Stinson, designed by Walter Burley Griffin who studied under Frank Lloyd Wright.

Top Winnetka Hotel Reviews

Find out more about Winnetka

There's nothing wrong with enjoying the finer things in life. Indulge your every whim on your impending break. There's no reason to delay a getaway to Winnetka any longer. You'll join the multitudes of vacationers who have made Winnetka so fashionable in the last few seasons. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. Don't wait any longer. Reserve one of our 5-star hotels in Winnetka and indulge in the finer things in life for a while.

Get a Great Deal on 5-Star Hotels in Winnetka

You'll have a wonderful time at one of these 5-star hotels. Excellent service, delicious meals, and attentive guest service are all at your fingertips. You're sure to find exactly the accommodation you need. You can also look forward to an outstanding experience and fantastic customer care, so get ready for a wonderful adventure. What creature comforts do you want in your lodging? A concierge to help you suggest the next attraction to visit? A rejuvenating facial treatment to help your cares fall away? Comfortable beds, piping hot coffees, and even spectacular views...these hotels will astonish you. Want to see for yourself? Explore our listings and pick the perfect accommodation for your needs.

Can't wait to get outside? We've got you covered. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what's on your agenda, the 5-star hotels in Winnetka are the perfect place to relax after a busy day.

Your Getaway Starts Today

The results are in, and Winnetka 5-star hotels are the place to be when you book your next vacation. If you've been dreaming about a vacation set here, then go ahead and book it. Expedia can help you land a great deal on accommodation. Your great getaway is just a mouse-click away. Select one of our Winnetka 5-star hotels today and relax in luxe surroundings tomorrow.

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Winnetka?

You can find a variety of pricing options for a 5-star hotel in Winnetka on Expedia. How much you'll pay will depend on your travel dates, trip length and other factors. Compare all of the available accommodations for your preferred dates and use our pricing and other filters to score the ideal upscale stay.

Search for the lowest price per night from $128

What makes a hotel 5 stars in Winnetka?

Exceptional guest service is integral to every 5-star hotel in Winnetka. From the second you arrive, staff attend to your every need, whether answering room service calls 24/7 or providing a nightly turn-down service. On top of that, hotels must offer top-rate conveniences to meet the standard for a 5-star rating. These can include luxury bath products, spas or saunas, swimming pools, fine dining restaurants and knowledgeable concierge.

Are there any 5-star all-inclusive resorts in Winnetka?

Expedia's filter tool is the quickest way to find exactly what you're looking for. Check the "All inclusive" and "5-star" boxes to see the most luxurious properties in Winnetka where your meals, lodging, activities and entertainment are included in the price. At these getaways, your trip is absolute indulgence from the moment you enter the lobby.

Room 1

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