Sleepy Hollow Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 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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    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Sleepy Hollow

Price found within the past 48 hours. Click for updated prices.
Red Roof Inn Hagerstown - Williamsport, MD

Red Roof Inn Hagerstown - Williamsport, MD

2 out of 5
Price was CA $695, price is now CA $695 per person
CA $695
per person
Apr 17 - Apr 19
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Hagerstown (HGR)
7.2/10 Good! (936 reviews)
I love staying here. The room is always clean and tidy, they check on you everyday or every other day and see if you need clean towels or toilet paper and they will take your dirty towels also. It is wonderful. I wish there was an easier way to reset the cards whenever you pay for another night but other than that, this place is always my go to. All of the workers are friendly. The desk clerks, the cleaners, and everyone I run into. It makes it pleasant when everyone is nice. They seem to all remember my name! 😊

Reviewed on Mar 2, 2026

Holiday Inn Express & Suites Clear Spring by IHG

Holiday Inn Express & Suites Clear Spring by IHG

2.5 out of 5
Price was CA $751, price is now CA $746 per person
CA $746
per person
Apr 17 - Apr 19
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Hagerstown (HGR)
8.4/10 Very Good! (1,002 reviews)
Quiet night sleep and a great breakfast

Reviewed on Feb 25, 2026

Sleepy Hollow Hotel Deals

Secluded Cabin: Hot Tub, Huge Deck, Fire Pit, WiFi

Secluded Cabin: Hot Tub, Huge Deck, Fire Pit, WiFi

Hedgesville WV
The price is CA $187 per night from Mar 16 to Mar 17
CA $187
CA $360 total
Mar 16 - Mar 17
includes taxes & fees
9.2/10 Wonderful! (10 reviews)
Very clean place with easy to use kitchen and living space. Hot tub was a fun edition! Great weekend with friends.

Reviewed on Feb 16, 2026

Secluded Cabin: Hot Tub, Huge Deck, Fire Pit, WiFi
Secluded WV Retreat Hot Tub, Fire Pit & Kayaks

Secluded WV Retreat Hot Tub, Fire Pit & Kayaks

Hedgesville WV
The price is CA $125 per night from Mar 22 to Mar 23
CA $125
CA $402 total
Mar 22 - Mar 23
includes taxes & fees
9.8/10 Exceptional! (13 reviews)
Everything was great, the property was just as the pictures showed. We had an awesome view and got lucky to see the northern lights during our stay.

Reviewed on Jan 23, 2026

Secluded WV Retreat Hot Tub, Fire Pit & Kayaks
Secluded 3-bedroom, 2-loft lakefront house in private Sleepy Hollow community.

Secluded 3-bedroom, 2-loft lakefront house in private Sleepy Hollow community.

Hedgesville WV
9.2/10 Wonderful! (5 reviews)
Great communication before our stay, clear and easy entry instructions, the house was crazy and as advertised. WiFi signal was a little weak, but there’s so much else to do, it’s not really a problem.

Reviewed on Feb 18, 2026

Get rates
Secluded 3-bedroom, 2-loft lakefront house in private Sleepy Hollow community.
See all 618 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.
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Frequently asked questions

How much does a Sleepy Hollow vacation package cost?
Live it up in Sleepy Hollow from just CA $695. We offer a wonderful selection of flights, hotels and rental cars to suit every budget and style. Land even more discounts when you add a couple of tours or experiences to your package.
How do I get a cheap travel package to Sleepy Hollow?
Combine your bookings with Expedia to save big bucks on your next big adventure. With more than 550 partner airlines and 1,000,000 hotels throughout the world, your Sleepy Hollow vacation package can be customized exactly to suit your budget. With all that extra cash, why not throw in one or two fun tours and activities? It's an easy way to unlock even more discounts. The vacation you've always dreamed of in Sleepy Hollow is closer than you thought!
What are the top hotels in Sleepy Hollow?
If this will be your first visit to Sleepy Hollow, make a reservation at Hot Tub, Fire Pit, Huge Deck At Loft Cabin or Above Sleepy Hollow - A Hidden Getaway. Both will make you feel at home and are popular options with lots of travelers.
How far in advance should I book my Sleepy Hollow vacation?
While not all air carriers advertise tickets early, you can normally start comparing international airfares on Expedia up to 12 months in advance. This is the time you'll nab some incredible bargains. If you're booking late, you might still be in luck. Low prices sometimes become available a few weeks prior to departure.
What does an Expedia Sleepy Hollow travel package include?
That depends on you. You can choose from a range of Sleepy Hollow packages, such as a flight, hotel and rental car. You can also book a hotel and a flight, or a flight with a rental car. Once you've made your booking, you can add on the fun stuff like experiences and tours. Whatever your ideal Sleepy Hollow trip looks like, you're sure to save!
What should I know before booking a Sleepy Hollow travel package?
You'll land amazing savings when you bundle your flights, hotels and rental cars into a package. Not only that, booking everything in one spot makes trip planning much easier. So why waste your money or time? Whether you're putting together a ritzy romantic getaway or an affordable family break, explore our vacation packages today.
Can I choose my airline with a Sleepy Hollow Expedia vacation package?
Yes — that's one of the best things about an Expedia package. You get to choose. We have more than 550 partner airlines all over the world, so you have lots of choice when arranging your Sleepy Hollow trip.
If I'm not able to travel, can I cancel my Sleepy Hollow vacation package?
Plans can change suddenly, so yes. You may be able to cancel or change your Sleepy Hollow vacation package at no cost if you've booked in the last 24 hours. For older bookings, you can still make the necessary changes, but your car rental company, airline or hotel may impose a fee. Need more information? Take a look at our Customer Service Portal. We're here to help make sure your getaway goes off without a hitch.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.