Sleepy Hollow Vacations from $451

Book a Hotel + Flight or Car together to unlock savings

Your Sleepy Hollow Vacation

When you book a Sleepy Hollow vacation package, it's all about enjoying your adventure to the fullest. Delve into the best things about this exciting city knowing that everything has been taken care of in advance. If taking in sights is part of the plan during your trip to Sleepy Hollow, check out big attractions like Santas Village, Grand Victoria Casino and NOW Arena. Whoever you're taking a break with and whatever you want to spend, your dream Sleepy Hollow vacation is just a few clicks away with Expedia.

The Latest Sleepy Hollow Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Ambassador Chicago, part of JdV by Hyatt

Ambassador Chicago, part of JdV by Hyatt

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 4 - Jul 9
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.8/10 Excellent! (1,002 reviews)
The Ambassador is one of my favorite places to stay while visiting Chicago. Though, born and raised from Chicago, the ambassador is placed in the rich and lush area in the Gold coast neighborhood in Chicago. There's plenty to do and various lovely restaurants, luxury clothing shops, beautiful architecture and transportation nearby. The hotel itself is legendary for having renowned guests in its history. Its comfortable, lively, accessible, and staff is really keen to help and serve numerous guests whom stay. I highly recommend for people to book and stay. Plan to comeback and stay again :)

Reviewed on May 20, 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
Aug 1 - Aug 4
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9.2/10 Wonderful! (96 reviews)
Outstanding service and facility.

Reviewed on Jan 10, 2024

Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 1 - Aug 4
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.4/10 Very Good! (1,003 reviews)
Had an amazing time! Room cleaners were very sweet and

Reviewed on May 6, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 1 - Aug 4
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9.2/10 Wonderful! (1,190 reviews)
The best hotel hands down!

Reviewed on May 13, 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 1 - Aug 4
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.8/10 Excellent! (207 reviews)
Thoroughly enjoyed my stay and my room. Will definitely book here again. Basic view of the courtyard but that was not important to me.

Reviewed on Mar 16, 2024

Sleepy Hollow Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
3,300
Top Sights
Santas Village, Hemmens Cultural Center and Epic Air Trampoline Park

Sleepy Hollow Hotel Deals

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 $52 per night from Jun 12 to Jun 13
$52
$60 total
includes taxes & fees
Jun 12 - Jun 13
6.4/10 (1,003 reviews)
"I liked how private and safe this motel felt"

Reviewed on May 17, 2024

Motel 6 Rolling Meadows, IL - Chicago Northwest
Holiday Inn Chicago - Elk Grove, an IHG Hotel
Holiday Inn Chicago - Elk Grove, an IHG Hotel
3.5 out of 5
1000 Busse Rd, Elk Grove Village, IL
Fully refundable
The price is $88 per night from Jun 2 to Jun 3
$88
$99 total
includes taxes & fees
Jun 2 - Jun 3
7.6/10 Good! (1,002 reviews)
"Easy relaxing place to stay, staff considerate and pleasant"

Reviewed on May 8, 2024

Holiday Inn Chicago - Elk Grove, an IHG Hotel
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 $119 per night from Jun 2 to Jun 3
$119
$152 total
includes taxes & fees
Jun 2 - Jun 3
8.4/10 Very Good! (1,003 reviews)
"Average"

Reviewed on May 12, 2024

Eaglewood Resort and Spa
See all 517 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Sleepy Hollow vacation package cost?
From as low as $451. 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.