Are there any 5-star vacation rentals in Crestwood?

There are no 5-star vacation rentals in Crestwood on our site, but there are a range of other top-rated properties worth looking into. Browse our vacation rentals in Crestwood to find the best place for your stay.

The Best 5 Star Hotels in Crestwood, IL from $117

A serene lake with reflections of trees and a cloudy sky.

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Our top choices for Crestwood 5-star hotels

A person sitting by a window with a view of a cityscape, including a tall tower.

1. Four Seasons Hotel Chicago

Downtown Chicago

ryan

$435 nightly

Dec 15 - Dec 16

Total with taxes and fees

A cityscape with a river, a bridge, and a dining area with tables and chairs.

2. Trump International Hotel & Tower Chicago

Downtown Chicago

Matthew

$394 nightly

Dec 13 - Dec 14

Total with taxes and fees

A rooftop bar with seating and a view of the city skyline at night.

3. The Peninsula Chicago

Downtown Chicago

Vincent Haley

$525 nightly

Dec 13 - Dec 14

Total with taxes and fees

A spacious lobby with a modern sofa, armchairs, and a coffee table. A large window offers a view of the cityscape.

4. The Langham, Chicago

Downtown Chicago

Talia

$435 nightly

Dec 13 - Dec 14

Total with taxes and fees

A black luxury car parked in front of a hotel entrance with a glass canopy decorated with festive ornaments.

5. Waldorf Astoria Chicago

Downtown Chicago

Loai

$438 nightly

Dec 13 - Dec 14

Total with taxes and fees

A modern indoor space with a glass ceiling, marble flooring, and contemporary furniture.

6. The Ritz-Carlton, Chicago

Downtown Chicago

Krikour

$371 nightly

Dec 13 - Dec 14

Total with taxes and fees

A modern hotel room with a large window offering a city view, a wooden desk with a laptop, and a small seating area.

7. Nobu Hotel Chicago

Downtown Chicago

Mauro

$354 nightly

Nov 22 - Nov 23

Total with taxes and fees

A couple dining at a table with a view of a cityscape and a sunset.

8. Park Hyatt Chicago

Downtown Chicago

Tom

$425 nightly

Dec 13 - Dec 14

Total with taxes and fees

A restaurant with tables and chairs arranged in a corridor, large windows, and hanging lamps.

9. The St. Regis Chicago

Downtown Chicago

Alise

$563 nightly

Dec 3 - Dec 4

Total with taxes and fees

A rooftop lounge with a city skyline view, featuring a sofa set with patterned cushions and a table with drinks and snacks.

10. Art Villa

West Town

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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 Crestwood.

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

172 W Adams St Chicago IL

$139 nightly

$165 total

Nov 22 - Nov 23

Total with taxes and fees

8.6/10 Excellent! (1,002 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 Crestwood

Explore the sprawling Playfield Park where locals gather for weekend softball tournaments and picnics under shady oak trees. Visit Caesar Park's splash pad in summer, then grab a slice at the family-owned Aurelio's Pizza that's been serving locals since 1959.

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Top Crestwood Hotel Reviews

Find out more about Crestwood

Why not demand the best on your jaunt to Crestwood? After all, you love the finer things in life, both at home and when you book a getaway. You'll join the multitudes of vacationers who have made Crestwood so popular in the last year. There's no reason to delay a getaway to Crestwood any longer. Besides, the accommodations in Crestwood offer great customer service, averaging 3.6 in our ranking system, so you know you're in good hands. Reserve one of our 5-star hotels in Crestwood and indulge in the finer things in life for a while. What are you waiting for?

Get a Great Deal on 5-Star Hotels in Crestwood

You can expect high quality from your hotel. Exceptional customer care, luxurious bedding, and rejuvenating spa offerings are all on offer. You're sure to find exactly the accommodation you need. You'll be pleased to note that the hotels in Crestwood offer great customer service, averaging 3.8 in our ranking system, setting you up for a truly relaxing getaway. How do you want to relax? A concierge to help you suggest the next attraction to visit? A Swedish massage to help your cares fall away? Comfortable beds, delectable chocolate desserts, and even spectacular views...these hotels are one-of-a-kind. Want to see for yourself? Plenty of visitors recommend this location.

Yearning for experiences outside your hotel room? You're in luck. 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 Crestwood are waiting for you to relax after an exciting day.

Make Your Escape

The results are in, and Crestwood 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. Expedia can help you land a great deal on accommodation. It's time to plan your next great escape. Decide on one of the 5-star hotels in Crestwood today and settle down in the lap of luxury tomorrow.

Frequently asked questions

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

The amount you pay for a 5-star hotel in Crestwood depends on factors such as when you plan to travel and the length of your trip. Our top tip for scoring an awesome deal? Use our pricing filters to compare the available hotels for your preferred dates.

Search for the lowest price per night from $117

What makes a hotel 5 stars in Crestwood?

From fine dining restaurants and 24/7 fitness centers to swimming pools and luxury bedding, the 5-star experience in Crestwood is all about luxury and comfort. But it takes more than just top-notch perks to earn a 5-star rating. Accommodations also have to offer exceptional guest-centric services like massage treatments, dry cleaning and laundry and room service any time day or night.

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

Find an indulgent getaway that includes your room, meals, drinks and entertainment in Crestwood with Expedia's filters. Search for properties with a 5-star rating and click on the "All inclusive" filter. Have a look at what's included in the price. This way, you'll be ready to maximize the many perks on offer from the moment you get there.

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Things to do in Chicago

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