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Jun 19 - Jun 21
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Top hotels in Sleepy Hollow

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $166 total per night from Jul 1 to Jul 2
$166 total
Jul 1 - Jul 2
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Express ...
"The entire staff was amazing!"

Reviewed on Jun 13, 2026

Opens in a new windowHilton Chicago/Magnificent Mile Suites
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $154 total per night from Jun 28 to Jun 29
$154 total
Jun 28 - Jun 29
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, free WiFi in public areas, and ...
"Overall stay was great with my brother. I will come back agin. Staff were helpful especially with our shuttle ride to the airport."

Reviewed on Jun 13, 2026

Opens in a new windowHyatt Regency O'Hare Chicago
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
$229 nightly
The price is $269 total per night from Jul 5 to Jul 6
$269 total
Jul 5 - Jul 6
Total with taxes and fees
This hotel features 2 restaurants, a bar/lounge, and A 24-hour gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, ...
"Welcoming, helpful staff, Clean, quiet room, Lovely, comfortable Hilton bed. Outstanding fitness room with new Life Fitness equipment! Great breakfast and Honors benefits, Just steps to terminal and train service."

Reviewed on Jun 13, 2026

Opens in a new windowHilton Chicago O'Hare Airport
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
$154 nightly
The price is $183 total per night from Jun 29 to Jun 30
$183 total
Jun 29 - Jun 30
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, ...
"This review reflects both the hotel and Expedia’s handling of the booking. The good: The location is excellent and very accessible. The common areas, including the lobby and bar, are pleasant and well maintained. The bad: The hotel is showing its age. The AC struggled to keep the room comfortable ..."

Reviewed on Jun 13, 2026

Opens in a new windowThe Chicago Hotel Collection Ambassador Gold Coast
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
$193 nightly
The price is $229 total per night from Jul 1 to Jul 2
$229 total
Jul 1 - Jul 2
Total with taxes and fees
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet ...
"the only issue i had it was that they didn’t do room service in the room, no new towels , no toilet paper and stuff like that"

Reviewed on Jun 12, 2026

Opens in a new windowHotel Felix River North/Magnificent Mile
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$136 nightly
The price is $162 total per night from Jun 29 to Jun 30
$162 total
Jun 29 - Jun 30
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 ...
"Great check-in and good value for money. We had a huge room with high ceilings and an amazing view of the water, marina, museums. Staff were all super friendly, warm and helpful. A little dilapidated due to its history but we understand the hotel is slowly getting renovated. Would recommend."

Reviewed on Jun 14, 2026

Opens in a new windowCongress Plaza Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street Chicago IL
Fully refundableReserve now, pay when you stay
$121 nightly
The price is $144 total per night from Jul 5 to Jul 6
$144 total
Jul 5 - Jul 6
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 ...
"It’s convenient location"

Reviewed on Jun 14, 2026

Opens in a new windowFreehand Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
$146 nightly
The price is $174 total per night from Jun 30 to Jul 1
$174 total
Jun 30 - Jul 1
Total with taxes and fees
This boutique hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Business travelers can take advantage of the free WiFi ...
"The hotel was a great location and very clean and and staff was nice and friendly!"

Reviewed on Jun 14, 2026

Opens in a new windowThe Chicago Hotel Collection - Magnificent Mile
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $161 total per night from Jul 1 to Jul 2
$161 total
Jul 1 - Jul 2
Total with taxes and fees
This hotel features a restaurant, a coffee shop, and free WiFi in public areas. Express check-out, luggage storage, and free newspapers are also on offer.
"This is an older building with some character. The friendly staff, good air conditioning and strong shower made it a comfortable stay."

Reviewed on Jun 13, 2026

Opens in a new windowTravelodge by Wyndham Downtown 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

Congress Plaza Hotel

Congress Plaza Hotel

4 out of 5
Posted less than an hour ago
Travelocity Verified Review
"Great check-in and good value for money. We had a huge room with high ceilings and an amazing view of the water, marina, museums. Staff were all super friendly, warm and helpful. A little dilapidated due to its history but we understand the hotel is slowly getting renovated. Would recommend."
A verified traveler stayed at Congress Plaza Hotel
Congress Plaza Hotel

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