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Nov 13 - Nov 15
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Top hotels in Sleepy Hollow

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4 out of 5
71 E Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
$161 nightly
The price is $191 total per night from Nov 23 to Nov 24
$191 total
Nov 23 - Nov 24
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, conference space, and valet ...
"This hotel was spectacular. Very aesthetic and clean, friendly staff and in a perfect area with plenty of locations to walk to."

Reviewed on Nov 11, 2026

Opens in a new windowThe Royal Sonesta Chicago Downtown
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$162 nightly
The price is $190 total per night from Nov 27 to Nov 28
$190 total
Nov 27 - Nov 28
Total with taxes and fees
This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, ...
"A perfect location . Great staff."

Reviewed on Nov 11, 2026

Opens in a new windowHilton Chicago
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $127 total per night from Nov 22 to Nov 23
$127 total
Nov 22 - Nov 23
Total with taxes and fees
This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center ...
"Honestly not my favorite stay, but it was in a super convenient location. We stayed three nights, and checked in pretty late. The hotel is very old in a sense of no modern amenities, no microwave in the room but has a great and comfortable vintage aesthetic. Was also told that it’s haunted with lore ..."

Reviewed on Nov 11, 2026

Opens in a new windowCongress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$187 nightly
The price is $195 total per night from Dec 8 to Dec 9
$195 total
Dec 8 - Dec 9
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, ...
"Excellent stay! Will definitely seek this property out again for my stay in Chicago"

Reviewed on Nov 11, 2026

Opens in a new windowThe Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
$106 nightly
The price is $126 total per night from Dec 10 to Dec 11
$126 total
Dec 10 - Dec 11
Total with taxes and fees
A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. ...
Opens in a new windowRiver Hotel
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $141 total per night from Nov 23 to Nov 24
$141 total
Nov 23 - Nov 24
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public ...
Opens in a new windowThe Wade
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $138 total per night from Nov 22 to Nov 23
$138 total
Nov 22 - Nov 23
Total with taxes and fees
This boutique hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi ...
Opens in a new windowThe Chicago Hotel Collection - Magnificent Mile
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
172 W Adams St Chicago IL
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $165 total per night from Nov 22 to Nov 23
$165 total
Nov 22 - Nov 23
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public ...
Opens in a new windowTHE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
200 North Columbus Drive Chicago IL
Fully refundableReserve now, pay when you stay
$229 nightly
The price is $272 total per night from Nov 22 to Nov 23
$272 total
Nov 22 - Nov 23
Total with taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities and in-room ...
Opens in a new windowFairmont Chicago at Millennium Park
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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.

Sleepy Hollow Hotel Guide

Don’t keep your travel plans on repeat year after year. The same city with the same hotel every season will bore you and give you an itch to go looking for something new. Expand your geographical horizons to more than just those five blocks around your usual haunt.

Nowhere else can you find better deals on Sleepy Hollow area hotels. You’ll find the best prices on the quirky, the haunted, the old, the new, and the legendary. If you’re wondering what side of the pricing scale some of these hotels fall on, you need not to worry. Compare cheap hotels near Sleepy Hollow to find the perfect one to will fit your budget.

Leave the ordinary routine you’re set on behind and go. Go anywhere you want. Anywhere that makes you think, “I wonder what that’s like?” Part of Travelocity’s mission is to get you off-the-beaten path and the hotels near Sleepy Hollow are perfect for that. Find your new favorite watering hole on a quiet street. Discover a place to escape for the weekend with tasty local fare and unique sights. We want you to consider the places outside your normal comfort zone. Browse our selection and find the ideal hotel, in a place you’d like to explore.

Recent Sleepy Hollow hotel reviews by fellow wanderers

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

5 out of 5
Posted less than an hour ago
Travelocity Verified Review
"Excellent stay! Will definitely seek this property out again for my stay in Chicago"
A verified traveler stayed at The Chicago Hotel Collection Ambassador Gold Coast
The Chicago Hotel Collection Ambassador Gold Coast

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