Are there any 5-star vacation rentals in Sleepy Hollow?

There are no 5-star vacation rentals in Sleepy Hollow on our site, but there are some other highly rated options worth looking into. Scan through our vacation rentals in Sleepy Hollow to book the ideal place for your getaway.

The Best 5 Star Hotels in Sleepy Hollow, IL from AED 527

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Our top choices for Sleepy Hollow 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

Edda

AED 2,271 total

includes taxes & fees

15 Nov - 16 Nov

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

2. Trump International Hotel & Tower Chicago

Downtown Chicago

Cecille

AED 2,014 total

includes taxes & fees

1 Nov - 2 Nov

A modern hotel lobby with a reception desk, seating area, and large windows offering city views.

3. The Langham, Chicago

Downtown Chicago

Saramae

AED 2,280 total

includes taxes & fees

15 Nov - 16 Nov

A high-rise hotel with multiple floors, large windows, and a prominent Tiffany & Co. store on the ground level.

4. The Peninsula Chicago

Downtown Chicago

Melinda

AED 2,729 total

includes taxes & fees

1 Nov - 2 Nov

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

Luis

AED 2,283 total

includes taxes & fees

15 Nov - 16 Nov

A modern indoor swimming pool with a clear blue water surface, a wooden ceiling, and a wall with a floral pattern.

6. Nobu Hotel Chicago

Downtown Chicago

Abhay

AED 2,078 total

includes taxes & fees

15 Nov - 16 Nov

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

7. Park Hyatt Chicago

Downtown Chicago

Tom

AED 2,401 total

includes taxes & fees

1 Nov - 2 Nov

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

8. The Ritz-Carlton, Chicago

Downtown Chicago

Krikour

AED 2,209 total

includes taxes & fees

1 Nov - 2 Nov

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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 Sleepy Hollow.

River Hotel

75 East Wacker Drive Chicago IL

AED 559

AED 664 total

1 Nov - 2 Nov

includes taxes & fees

8.8/10 Excellent! (5,542 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.

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Frequently asked questions

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

The amount you pay for a 5-star hotel in Sleepy Hollow depends on things like when you plan to travel and the length of your escape. A top tip for bagging an awesome deal? Use our pricing filters to compare all of the available options for your selected dates.

Search for the lowest price per night from AED 527

What makes a hotel 5 stars in Sleepy Hollow?

From fine dining venues and 24/7 fitness centers to pools and deluxe bedding, the 5-star experience in Sleepy Hollow is all about luxury and comfort. But it requires more than just top-notch amenities to receive a 5-star rating. Stays also have to provide extraordinary guest-centric services like beauty treatments, dry cleaning and laundry and 24-hour room service.

Are there any 5-star all-inclusive resorts in Sleepy Hollow?

Find an upscale stay that includes your lodging, meals, bar and entertainment in Sleepy Hollow with our filter tool. Search for hotels with a 5-star rating and select the "All inclusive" filter. Have a look at what's included in the price. That way, you're ready to take advantage of all the perks on offer from the moment you arrive.

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