Sleepy Hollow Holidays

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Top Flight + Hotel Deals in Sleepy Hollow

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
per person
26 Dec - 30 Dec
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.4/10 Very Good! (1,387 reviews)
Booked a lake view room and got a partial view. I definitely wouldn’t have payed more if I knew it was partial

Reviewed on 25 Nov 2024

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
26 Dec - 30 Dec
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (931 reviews)
The property was aesthetically pleasing and we received excellent service from the front desk and bellman. I wanted to love this hotel however the refrigerator and the room repeatedly made humming sounds. The mattress was really hard. You could hear the elevators running all hours of the evening while trying to sleep and the air conditioning unit did not work as expected. I did appreciate the location and the staff’s kindness and willingness to help. I’d be willing to stay again with a different room with fewer noises and a more comfortable mattress.

Reviewed on 26 Nov 2024

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
26 Dec - 30 Dec
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,378 reviews)
Very nice hotel! We had a beautiful room with a fantastic view ! 5 minutes away from Millenium park and accessible to all touristic areas!

Reviewed on 26 Nov 2024

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
26 Dec - 30 Dec
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (809 reviews)
This was a lovely hotel right in the heart of Fulton market area. Such a fun vibrant area! Hotel was clean, beautiful, and all Staff were helpful and kind. The hotel bars and restaurants were very good with great ambiance.

Reviewed on 26 Nov 2024

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
per person
26 Dec - 30 Dec
found 20 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Great, small hotel in the heart of Chicago, Amazing attention to detail very comfortable room well appointed

Reviewed on 25 Nov 2024

Top hotels in Sleepy Hollow

Country Inn & Suites by Radisson, Schaumburg, IL
Country Inn & Suites by Radisson, Schaumburg, IL
3 out of 5
1401 North Roselle Road, Schaumburg, IL
Fully refundable
The price is €101 per night from 22 Dec to 23 Dec
€101
includes taxes & fees
22 Dec - 23 Dec
8.6/10 Excellent! (1,005 reviews)
"I highly recommend"

Reviewed on 23 Nov 2024

Country Inn & Suites by Radisson, Schaumburg, IL
Hyatt Regency Schaumburg Chicago
Hyatt Regency Schaumburg Chicago
4 out of 5
1800 East Golf Rd, Schaumburg, IL
The price is €118 per night from 9 Dec to 10 Dec
€118
includes taxes & fees
9 Dec - 10 Dec
8/10 Very Good! (1,017 reviews)
"I really liked this hotel, the aesthetic during the holidays was for sure a bonus, 10/10 recommend"

Reviewed on 24 Nov 2024

Hyatt Regency Schaumburg Chicago
Motel 6 Rolling Meadows, IL - Chicago Northwest
Motel 6 Rolling Meadows, IL - Chicago Northwest
2 out of 5
1800 Winnetka Cir, Rolling Meadows, IL
Fully refundableReserve now, pay when you stay
The price is €56 per night from 9 Dec to 10 Dec
€56
includes taxes & fees
9 Dec - 10 Dec
6.6/10 (1,011 reviews)
"Nothing to complain about with this motel 6."

Reviewed on 21 Nov 2024

Motel 6 Rolling Meadows, IL - Chicago Northwest
See all 503 properties in Sleepy Hollow
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.

Frequently asked questions

How much does a Sleepy Hollow holiday package cost?
From as low as €653. Yes, you read that correctly. Our Sleepy Hollow packages are an easy way to stretch your budget further. Combine your preferred hotels, flights and rental car and get out and see this exciting destination.
How do I get a cheap travel package to Sleepy Hollow?
Bundle your hotels and flights with Expedia to save big bucks on your next big adventure. With more than 550 partner airlines and 1,000,000 hotels around the globe, your Sleepy Hollow holiday package can be tailored exactly to suit your travel style. With all that extra money, why not throw in one or two fun experiences and tours? It’s an easy way to unlock even more discounts. That dream holiday to Sleepy Hollow is closer than you thought!
Where should I stay in Sleepy Hollow?
A trip to Sleepy Hollow isn’t complete without stopping by Santas Village, Advocate Sherman Hospital and Randall Oaks Golf Club. Spend your nights close to these attractions and make sightseeing a breeze.
How far in advance should I book my Sleepy Hollow holiday?
Your best bet is to book early. Air carriers typically release flight tickets up to 12 months in advance, and this is your chance to score some of the lowest prices. Just been told you should take all your holiday days in a few weeks? That’s alright! Expedia are never short on fantastic deals to send you off on the getaway of your dreams, at an affordable price.
What does an Expedia Sleepy Hollow travel package include?
Hotels, flights and a shiny set of wheels for all your road trip adventures. Simply pick and choose your preferred bundle and get access to incredible deals. Once you’ve made your booking, add on a couple of activities and tours and watch your savings pile up. When it comes to creating your Sleepy Hollow break, you’re in control!
What should I know before booking a Sleepy Hollow travel package?
So many places to explore, so many things to experience. With a travel package, you can check more of them off your list. Combine your hotels, rental cars and flights and land big savings.
Can I choose my airline with a Sleepy Hollow Expedia holiday package?
Yes, and with over 550 airlines to pick from worldwide, you’re spoiled for choice. Look through the available options and see which airline suits your budget and needs.
If I'm not able to travel, can I cancel my Sleepy Hollow holiday package?
If your holiday plans in Sleepy Hollow have been upended, it’s good to know that it’s possible to cancel or amend your booking. If you made your booking in the last 24 hours, you may be able to receive a refund. If your booking is older than that, your airline, hotel or car rental company may charge fees. To learn more, check our Customer Service Portal.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.