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Your Sleepy Hollow Vacation
Entertainment, history, art and more … There's so much to experience with a Sleepy Hollow vacation package. And with the ability to customize your city getaway, it's guaranteed to be one you won't forget. Make your trip to Sleepy Hollow even more fun by going sightseeing. Grand Victoria Casino, Santas Village and NOW Arena are among the top attractions worth exploring. Whatever your travel plans or budget, organizing your ultimate tailored Sleepy Hollow vacation is simple with Expedia.
Top Sleepy Hollow Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
Aug. 19 - Aug. 23
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (1,212 reviews)
Love this property. Whenever we visit Chicago this is where we stay. It’s lovely.
Reviewed on Jun. 12, 2024
Arlo Chicago
Downtown Chicago
Save 100% on your flight
per person
Aug. 19 - Aug. 23
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
8.8/10 Excellent! (1,114 reviews)
The hotel was great and guest services were awesome. Noted my late arrival due to delayed flight. The hotel is right on Michigan and the bus stops right in front. The rooms are comfortable and well designed.
However, I wouldn't recommend eating at ALK. What a rip. for $6, I got about 10 spears of grilled asparagus! I know food prices and labor have gone up but this is ridiculous.
Reviewed on Jun. 8, 2024
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
per person
Aug. 25 - Aug. 31
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.6/10 Exceptional! (983 reviews)
I would just improve the attention in the breakfast restaurant due to a bad experience. The rest was excellent
Reviewed on Jun. 2, 2024
The Chicago Hotel Collection - Wrigleyville
Lakeview
Save 100% on your flight
per person
Aug. 23 - Aug. 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
6.6/10 (603 reviews)
Perfect place to stay if going to a cubs game or spending the night in the area. The hotel service was phenomenal. The room was clean, decorative and very stylish. Highly recommend and look forward to staying there again.
Reviewed on Jun. 3, 2024
Sleepy Hollow Hotel Deals
Wyndham Garden Schaumburg Chicago Northwest
1725 E Algonquin Road, Schaumburg, IL
Fully refundableReserve now, pay when you stay
The price is CA $115 per night from Jul. 1 to Jul. 2
CA $115
CA $133 total
includes taxes & fees
Jul 1 - Jul 2
6.8/10 (1,003 reviews)
"A good budget friendly place to stay if you are trying to save a buck while attending a convention. It's a nice 10ish min walk from the back of the hotel on a pathway, around a beautiful pond, and up a small grassy knoll to parking lot."
Reviewed on Jun. 11, 2024
Motel 6 Rolling Meadows, IL - Chicago Northwest
1800 Winnetka Cir, Rolling Meadows, IL
Fully refundableReserve now, pay when you stay
The price is CA $79 per night from Jun. 26 to Jun. 27
CA $79
CA $91 total
includes taxes & fees
Jun 26 - Jun 27
6.4/10 (1,001 reviews)
"pool covered with tarp, not in working condition for years. lobby with bullet proof glass over reception area desk & over 20 security camera images give initial perception of unsafe area but had no problems"
Reviewed on Jun. 10, 2024
Eaglewood Resort and Spa
1401 Nordic Rd, Itasca, IL
Fully refundableReserve now, pay when you stay
The price is CA $164 per night from Jun. 23 to Jun. 24
CA $164
CA $209 total
includes taxes & fees
Jun 23 - Jun 24
8.4/10 Very Good! (1,001 reviews)
"My Fiancé and I only stayed for the weekend. Staff was rude and needs to get it together, other than that and me not caring like a Karen, beautiful stay! Room was clean, but conditioner wasn’t filled & you could tell by the dust it wasn’t freshly cleaned (soap dish & lamps) tub was just stained no ..."
Reviewed on Jun. 7, 2024
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.