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Oct 16 - Oct 18
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Top hotels in Sleepy Hollow

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street Chicago IL
Fully refundableReserve now, pay when you stay
$149 nightly
The price is $177 total per night from Nov 11 to Nov 12
$177 total
Nov 11 - Nov 12
Total with taxes and fees
A full-service spa and a gym are featured at this boutique hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, ...
"Hands-down, always my favorite place to stay when I am in Chicago. I’ve been staying here for years. It’s essentially located so you can walk everywhere to the magnificent mile to the Gold Coast Beach to all of the shopping. Restaurants are right next to it. There is a true food, kitchen and a soul ..."

Reviewed on Oct 12, 2026

Opens in a new windowEurostars Magnificent Mile
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $171 total per night from Oct 25 to Oct 26
$171 total
Oct 25 - Oct 26
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. ...
"I absolutely loved this place. Close to everything and great view"

Reviewed on Oct 12, 2026

Opens in a new windowRiver Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$190 nightly
The price is $226 total per night from Oct 30 to Oct 31
$226 total
Oct 30 - Oct 31
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, ...
"5 star"

Reviewed on Oct 12, 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
$106 nightly
The price is $126 total per night from Nov 11 to Nov 12
$126 total
Nov 11 - Nov 12
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 ...
"Lakeview window. Odd shaped room but the view was stunning! Watched the sunrise and it was amazing! Love the older hotels and some of the quirky things. Bathroom door stuck and locked my husband on for a few minutes. Cannot set your own room temperature. You can only adjust the fan. We had to crack ..."

Reviewed on Oct 12, 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
$143 nightly
The price is $170 total per night from Nov 1 to Nov 2
$170 total
Nov 1 - Nov 2
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, ...
"The room is nice, big with a bed which is comfy and the Wi.Fi works just fine. It wasn't the cleanest. If you look a bit under the chairs or in the corners there was plenty of dust. Breakfast is ok and they were very kind to make an earlier one for the marathon"

Reviewed on Oct 12, 2026

Opens in a new windowThe Chicago Hotel Collection Ambassador Gold Coast
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
$142 nightly
The price is $169 total per night from Nov 1 to Nov 2
$169 total
Nov 1 - Nov 2
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 ...
"All of it."

Reviewed on Oct 12, 2026

Opens in a new windowThe Chicago Hotel Collection - Magnificent Mile
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $151 total per night from Nov 12 to Nov 13
$151 total
Nov 12 - Nov 13
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
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr Chicago IL
$354 nightly
The price is $421 total per night from Oct 25 to Oct 26
$421 total
Oct 25 - Oct 26
Total with taxes and fees
This smoke-free hotel's 4 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center, ...
Opens in a new windowHyatt Regency Chicago
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street Chicago IL
Fully refundableReserve now, pay when you stay
$178 nightly
The price is $211 total per night from Nov 2 to Nov 3
$211 total
Nov 2 - Nov 3
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Self parking, a coffee shop, and a snack bar/deli are also ...
Opens in a new windowFreehand Chicago
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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

Eurostars Magnificent Mile

Eurostars Magnificent Mile

5 out of 5
Posted 1 hour ago
Travelocity Verified Review
"Hands-down, always my favorite place to stay when I am in Chicago. I’ve been staying here for years. It’s essentially located so you can walk everywhere to the magnificent mile to the Gold Coast Beach to all of the shopping. Restaurants are right next to it. There is a true food, kitchen and a soul cycle right next to it as well and Tal nightclub is also right next-door. The staff is absolutely amazing in the rooms are luxurious for a great price."
A verified traveler stayed at Eurostars Magnificent Mile
Eurostars Magnificent Mile

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