Sleepy Hollow Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Save up to CA $775 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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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.
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
Jul. 18 - Jul. 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 18 - Jul. 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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

Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 18 - Jul. 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (97 reviews)
Outstanding service and facility.

Reviewed on Jan. 10, 2024

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 18 - Jul. 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (703 reviews)
Very good hotel in a central location very close to all attractions, shops and good restaurants

Reviewed on Jun. 9, 2024

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 18 - Jul. 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,015 reviews)
Very friendly and helpfu

Reviewed on May 31, 2024

Sleepy Hollow Hotel Deals

Wyndham Garden Schaumburg Chicago Northwest
Wyndham Garden Schaumburg Chicago Northwest
3 out of 5
1725 E Algonquin Road, Schaumburg, IL
Fully refundableReserve now, pay when you stay
The price is CA $115 per night from Jun. 24 to Jun. 25
CA $115
CA $133 total
includes taxes & fees
Jun 24 - Jun 25
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

Wyndham Garden Schaumburg Chicago Northwest
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 CA $79 per night from Jun. 24 to Jun. 25
CA $79
CA $91 total
includes taxes & fees
Jun 24 - Jun 25
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

Motel 6 Rolling Meadows, IL - Chicago Northwest
Eaglewood Resort and Spa
Eaglewood Resort and Spa
4 out of 5
1401 Nordic Rd, Itasca, IL
Fully refundableReserve now, pay when you stay
The price is CA $163 per night from Jul. 8 to Jul. 9
CA $163
CA $209 total
includes taxes & fees
Jul 8 - Jul 9
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

Eaglewood Resort and Spa
See all 524 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Sleepy Hollow vacation package cost?
From as low as CA $822. 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 vacation 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 vacation 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 vacation?
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 vacation 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 vacation 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 vacation package?
If your vacation 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.

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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.