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Sep 18 - Sep 20
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Sep 25 - Sep 27

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Top hotels in Sleepy Hollow

L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
225 N Wabash Ave Chicago IL
$284 nightly
The price is $337 total per night from Sep 20 to Sep 21
$337 total
Sep 20 - Sep 21
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a coffee shop, and a lobby fireplace are also ...
"We had a wonderful stay at L7 Chicago. From the moment we arrived, Antonio greeted us and was absolutely amazing—friendly, welcoming, and incredibly helpful. He truly set the tone for a great stay and made us feel welcome from the minute we walked in. The hotel was beautiful, comfortable, and in ..."

Reviewed on Sep 12, 2026

Opens in a new windowL7 Chicago by LOTTE
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $151 total per night from Sep 13 to Sep 14
$151 total
Sep 13 - Sep 14
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. ...
"Love my experience!!"

Reviewed on Sep 12, 2026

Opens in a new windowRiver 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
$179 nightly
The price is $213 total per night from Oct 13 to Oct 14
$213 total
Oct 13 - Oct 14
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, ...
Opens in a new windowThe Chicago Hotel Collection Ambassador Gold Coast
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$166 nightly
The price is $197 total per night from Sep 27 to Sep 28
$197 total
Sep 27 - Sep 28
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 ...
Opens in a new windowCongress Plaza Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$247 nightly
The price is $294 total per night from Sep 25 to Sep 26
$294 total
Sep 25 - Sep 26
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, ...
Opens in a new windowHilton Chicago
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
$144 nightly
The price is $172 total per night from Sep 20 to Sep 21
$172 total
Sep 20 - Sep 21
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
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr Chicago IL
$322 nightly
The price is $383 total per night from Sep 26 to Sep 27
$383 total
Sep 26 - Sep 27
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
Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

2.5 out of 5
160 E Huron Street Chicago IL
Fully refundableReserve now, pay when you stay
$203 nightly
The price is $242 total per night from Sep 20 to Sep 21
$242 total
Sep 20 - Sep 21
Total with taxes and fees
This hotel features free WiFi in public areas, laundry facilities, and valet parking. Enjoy the free continental breakfast each morning. Express check-in, express ...
Opens in a new windowHampton Inn Chicago Downtown/Magnificent Mile
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3 out of 5
201 East Walton Place Chicago IL
Fully refundableReserve now, pay when you stay
$181 nightly
The price is $215 total per night from Sep 27 to Sep 28
$215 total
Sep 27 - Sep 28
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free full breakfast and free WiFi. Traveling on business? Take advantage of the business center, express ...
Opens in a new windowSonesta ES Suites Chicago Downtown Magnificent Mile - Medical
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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

Congress Plaza Hotel

Congress Plaza Hotel

5 out of 5
Posted 4 hours ago
Travelocity Verified Review
"Love the Victorian vibes this place gives, as well as the updated modern rooms while still giving us that beautiful space to sleep in. Would recommend!"
A verified traveler stayed at Congress Plaza Hotel
Congress Plaza Hotel

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