Sleepy Hollow 5 Stars Hotels

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Check availability on Sleepy Hollow 5 Star Hotels

Tonight
Dec 1 - Dec 2
Tomorrow
Dec 2 - Dec 3
This weekend
Dec 5 - Dec 7
Next weekend
Dec 12 - Dec 14

Compare Sleepy Hollow 5 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Reception
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1005)
"Amazing hotel"
United States
David
The price is NT$13,184
NT$15,477 total
includes taxes & fees
Dec 14 - Dec 15
Four Seasons Hotel Chicago
Lobby
The Langham, Chicago

The Langham, Chicago

5.0 star property
Downtown Chicago
9.8 out of 10, Exceptional, (1009)
"Spa ,pool are awesome "
United States
jared
The price is NT$14,832
NT$17,412 total
includes taxes & fees
Dec 21 - Dec 22
The Langham, Chicago
Front of property - evening/night
The Peninsula Chicago

The Peninsula Chicago

5.0 star property
Downtown Chicago
9.8 out of 10, Exceptional, (1020)
"Great rooms, location and top flight service"
United States
Andrew
The price is NT$14,911
NT$17,504 total
includes taxes & fees
Jan 1 - 2026/1/2
The Peninsula Chicago
Bar (on property)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1792)
"Great stay "
United States
Mohammed
The price is NT$10,877
NT$12,769 total
includes taxes & fees
Jan 1 - 2026/1/2
Trump International Hotel & Tower Chicago
Exterior
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1008)
"The staff was amazing. Will be making a return stay."
United States
Patricia
The price is NT$11,929
NT$14,003 total
includes taxes & fees
Jan 1 - 2026/1/2
Waldorf Astoria Chicago
Suite, Terrace (Water Tower) | Premium bedding, down comforters, pillowtop beds, minibar
Park Hyatt Chicago

Park Hyatt Chicago

5.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1002)
"Stay was amazing!!! The staff was so friendly, kind, and thoughtful! The rooms were soooo beyond perfect and lovely! And the food at the restaurant was amazing.. especially breakfast! You won’t regret staying here!!! "
United States
Larissa
The price is NT$13,938
NT$16,361 total
includes taxes & fees
Jan 1 - 2026/1/2
Park Hyatt Chicago
Indoor pool, open 6:00 AM to 9:00 PM, sun loungers
Nobu Hotel Chicago

Nobu Hotel Chicago

5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (753)
"Great location, amenities and staff. "
United States
Nicholas
The price is NT$7,856
NT$9,222 total
includes taxes & fees
Dec 21 - Dec 22
Nobu Hotel Chicago
Bar (on property)
The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

5.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1005)
"Great breakfast a la carte menu, perfect bar setting, room was spotless, and service in accordance to the Ritz Brand."
United States
Alejandro Randolph
The price is NT$12,120
NT$14,228 total
includes taxes & fees
Dec 30 - Dec 31
The Ritz-Carlton, Chicago
2 restaurants, breakfast served
The St. Regis Chicago

The St. Regis Chicago

5.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (83)
"Nice place "
United States
John
The price is NT$14,000
NT$16,435 total
includes taxes & fees
Dec 17 - Dec 18
The St. Regis Chicago
Interior
Art Villa

Art Villa

5.0 star property
West Town
10.0 out of 10, Exceptional, (2)
" "
United States
tomonobu
Art Villa
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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.
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

600 N State St Chicago IL
The price is NT$2,888 per night from Dec 7 to Dec 8
NT$2,888
NT$3,390 total
Dec 7 - Dec 8
includes taxes & fees
8.4/10 Very Good! (5,350 reviews)
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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?
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$3,390

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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