Sleepy Hollow Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Your Sleepy Hollow Vacation

Lock in a custom vacation package to Sleepy Hollow and get ready for your next great escape. Stay in the neighborhood of Northwest Yonkers, which is great for nature and culture, for a real taste of this interesting city. Lyndhurst Mansion, Tarrytown Music Hall and Sleepy Hollow Cemetery are just some of the many sights worth checking out during your trip to Sleepy Hollow. Whatever your travel plans or budget, organizing a tailored Sleepy Hollow vacation is a walk in the park with Expedia.

Top Sleepy Hollow Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hyatt Regency Greenwich

Hyatt Regency Greenwich

4 out of 5
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
8.2/10 Very Good! (1,015 reviews)
Lovely property with beautiful atrium and surrounds. Breakfast only in room with digital ordering. Reasonable price. Dinner ok in nice atrium with massive TVs and loud noise, but good service by Suzy. Overall good experience.

Reviewed on Aug. 12, 2025

Delamar Southport

Delamar Southport

4 out of 5
per person
Oct 27 - Nov 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
9.4/10 Exceptional! (425 reviews)
the room is very noisy, window seal is bad as it is facing freeway. door has large gap and can hear people talking on hallway. not worth it for the price you pay.

Reviewed on Aug. 8, 2025

Sonesta White Plains Downtown

Sonesta White Plains Downtown

4 out of 5
per person
Oct 20 - Oct 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
8.6/10 Excellent! (1,096 reviews)
Stayed one night but wished I had more time. Beautiful hotel. Would stay here again when in the area

Reviewed on Aug. 12, 2025

Courtyard by Marriott Tarrytown Westchester County

Courtyard by Marriott Tarrytown Westchester County

3 out of 5
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to White Plains (HPN)
9/10 Wonderful! (1,001 reviews)
Dtayed her a few times and they never let me down!

Reviewed on Aug. 5, 2025

Sleepy Hollow Hotel

Sleepy Hollow Hotel

3.5 out of 5
per person
Oct 10 - Oct 12
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to White Plains (HPN)
6.6/10 (1,013 reviews)
It was a great stay. Staff was good and store was walkable. Pool time was excellent

Reviewed on Aug. 9, 2025

Ready to book your vacation to Sleepy Hollow?

 

Choose your dates

Sleepy Hollow Hotel Deals

Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

3 out of 5
200 West Main Street, Elmsford, NY
Fully refundableReserve now, pay when you stay
The price is CA $174 per night from Sep 1 to Sep 2
CA $174
CA $199 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (1,103 reviews)
"Very accessible, right off of the highway. The room was nice, bed was very comfortable."

Reviewed on Aug. 11, 2025

Hampton Inn White Plains/Tarrytown
Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

2.5 out of 5
540 Saw Mill River Rd, Elmsford, NY
Fully refundableReserve now, pay when you stay
The price is CA $198 per night from Aug 24 to Aug 25
CA $198
CA $226 total
Aug 24 - Aug 25
includes taxes & fees
8.2/10 Very Good! (1,395 reviews)
"N/A"

Reviewed on Aug. 9, 2025

Baymont by Wyndham White Plains - Elmsford
Executive Inn - Fort Lee

Executive Inn - Fort Lee

3.5 out of 5
2339 Route 4, Fort Lee, NJ
Fully refundableReserve now, pay when you stay
The price is CA $128 per night from Aug 17 to Aug 18
CA $128
CA $147 total
Aug 17 - Aug 18
includes taxes & fees
7.6/10 Good! (350 reviews)
"It was perfect and affordable!"

Reviewed on Aug. 9, 2025

Executive Inn - Fort Lee
See all 1,696 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

Discover the most popular places to visit in Sleepy Hollow

Lyndhurst Mansion

Lyndhurst Mansion

Learn about the local history of Tarrytown with a stop at Lyndhurst Mansion. Stroll along the riverfront in this family-friendly area, or check out its top-notch restaurants.

Lyndhurst Mansion

What to do in Sleepy Hollow

LEGOLAND® Discovery Center Westchester Tickets

LEGOLAND® Discovery Center Westchester Tickets

CA $42
per adult
76% of travellers recommend
LEGOLAND® Discovery Center Westchester Tickets
Helicopter landing in a field in New York

Introductory Helicopter Flight Lesson from Westchester

CA $918
per traveller
Introductory Helicopter Flight Lesson from Westchester
See all activities in Sleepy Hollow

Frequently asked questions

How much does a Sleepy Hollow vacation package cost?
You can snap up a vacation package to this popular destination from CA $722 on Expedia. However, how much your vacation to Sleepy Hollow costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Sleepy Hollow?
January, February and March are the best times to search for cheap Sleepy Hollow vacation packages. Travelling in less busy periods means you can generally find lower prices on flights and accommodations.
How many days is enough for Sleepy Hollow?
With a well-planned schedule, you can easily tick off the main Sleepy Hollow sights in a handful of days. But if you'd like to venture off the beaten track or go on day trips, consider booking your Sleepy Hollow vacation for longer.
Is it worth booking a vacation package to Sleepy Hollow?
Popular for its nature, culture and history, a Sleepy Hollow vacation is a hit with all kinds of travellers. Be sure to visit leading sights like Tarrytown Lighthouse and Old Dutch Church of Sleepy Hollow, and consider renting a set of wheels for day trips to experience even more.
How to find the best Sleepy Hollow package deals?
Begin your search for a Sleepy Hollow package deal by entering your travel dates and destination under our "Packages" tab. Then select a few filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Sleepy Hollow package deal straight away, simply change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Sleepy Hollow adventure off to a flying start.
Is it cheaper to book a Sleepy Hollow vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll typically get a better deal than booking each component individually. And you'll still have the flexibility to create a customized Sleepy Hollow vacation by choosing your favourite airline, accommodation type and car class.
When to book a vacation package to Sleepy Hollow?
Score incredible bargains by booking your flights ahead of time with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Sleepy Hollow trip.
How to plan a trip to Sleepy Hollow?

  1. Pick your travel dates: The things you plan to do in Sleepy Hollow and your favourite season can help you decide when to go.
  2. Set your budget: Consider costs such as flights, transportation and food when calculating how much to set aside for your trip to Sleepy Hollow. Then, pick a hotel that suits your budget, whether that's a wallet-friendly option or a high-end retreat.
  3. Work out your trip length: Think about how much time you'd like to spend exploring Sleepy Hollow. Plan your days so you can get to all the activities and attractions you're interested in at a comfortable pace.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to pick a Sleepy Hollow vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.