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

Our site doesn't offer any 5-star vacation rentals in Sleepy Hollow. However, you can still find a range of top-rated escapes where the only item on your itinerary will be to kick back and have fun. See what's available by searching through our vacation rentals in Sleepy Hollow .

5 Stars Hotels in Sleepy Hollow: Compare Hotel Prices & Find the Cheapest Sleepy Hollow, Chicago 5 Stars Hotels

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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

NT$19,738 total

includes taxes & fees

Nov 1 - Nov 2

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

2. Trump International Hotel & Tower Chicago

Downtown Chicago

Cecille

NT$17,508 total

includes taxes & fees

Nov 1 - Nov 2

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

3. The Langham, Chicago

Downtown Chicago

Saramae

NT$20,345 total

includes taxes & fees

Nov 1 - Nov 2

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

Levi

NT$24,672 total

includes taxes & fees

Nov 1 - Nov 2

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

NT$20,487 total

includes taxes & fees

Nov 1 - Nov 2

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

NT$18,059 total

includes taxes & fees

Nov 1 - Nov 2

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

7. Park Hyatt Chicago

Downtown Chicago

Tom

NT$20,770 total

includes taxes & fees

Nov 1 - Nov 2

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

8. The Ritz-Carlton, Chicago

Downtown Chicago

Fred

NT$19,197 total

includes taxes & fees

Nov 1 - Nov 2

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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

NT$4,858

NT$5,775 total

Oct 25 - Oct 26

includes taxes & fees

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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.

Top Sleepy Hollow Hotel Reviews

Frequently asked questions

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

How much you pay for a 5-star hotel in Sleepy Hollow depends on factors such as when you plan to go and the length of your break. An insider tip for landing the best deal? Use our pricing filters to check out all of the available options for your chosen dates.

Search for the lowest price per night from NT$5,427

What makes a hotel 5 stars in Sleepy Hollow?

In Sleepy Hollow, a hotel needs to offer a certain number of upscale amenities to earn a 5-star rating. These can include on-site gyms, saunas and spas, gourmet restaurants, premium bedding, luxury toiletries and more. What also sets 5-star hotels apart is their guest-focused service. You can look forward to things like nightly turn-down services, concierge services and in-room massages. Some may even offer extra touches such as welcome gifts.

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

Find a luxurious retreat that includes your lodging, meals, bar and entertainment in Sleepy Hollow with our filters. Search for resorts rated 5 stars and click on the "All inclusive" filter. Be sure to check what's included in the upfront price. That way, you can take full advantage of the premium perks on offer from the moment you arrive.

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