Sleepy Hollow Vacation Packages

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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.
Stamford Marriott

Stamford Marriott

Downtown Stamford
CA $771
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
8/10 Very good! (1,002 reviews)
Residence Inn Stamford Downtown

Residence Inn Stamford Downtown

Downtown Stamford
Save 100% on your flight
CA $1,153
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
9.4/10 Exceptional! (430 reviews)
Delamar Southport

Delamar Southport

CA $1,722
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
9.6/10 Exceptional! (517 reviews)
Stamford Suites

Stamford Suites

Downtown Stamford
CA $1,057
per person
Dec 11 - Dec 15
found 11 hours ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
6.4/10 (185 reviews)
This property is listed as a 3-star. There is NO WAY this is a 3-star property. It is much a motel or hostel at best. DO NOT STAY HERE. It was so dirty that I did not feel comfortable staying. I left after only a few minutes and they would not process a refund. There were people banging on doors and yelling in the hallway and there were people smoking substances in the parking lot. This is the worst accommodation I've ever booked!

Reviewed on Oct 5, 2026

Hyatt Regency Greenwich

Hyatt Regency Greenwich

CA $1,213
per person
Dec 26 - Dec 30
found 14 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to White Plains (HPN)
8.8/10 Excellent! (1,155 reviews)
Great stay , easy valet parking, nice amenities ..will be back.

Reviewed on Oct 10, 2026

Ready to book your vacation to Sleepy Hollow?

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Sleepy Hollow Hotel Deals

Highbridge Hotel

Highbridge Hotel

1263 Edward L Grant Highway Bronx NY
Fully refundableReserve now, pay when you stay
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Highbridge Hotel
Executive Inn - Fort Lee

Executive Inn - Fort Lee

2339 Route 4 Fort Lee NJ
Fully refundableReserve now, pay when you stay
Get rates
Executive Inn - Fort Lee
Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

540 Saw Mill River Rd Elmsford NY
Fully refundableReserve now, pay when you stay
Get rates
Baymont by Wyndham White Plains - Elmsford
See all 1,802 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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Stay near popular Sleepy Hollow attractions

A lighthouse with a white and red base, a black top, and a metal railing.
Photo by Bob Westerfield

Tarrytown Lighthouse

8.4/10 (104 reviews)
You can learn about the history of Sleepy Hollow with a stop at Tarrytown Lighthouse. Stroll along the riverfront in this quaint area, or check out its top-notch restaurants.
See properties
A white house with a wooden deck and a wooden bridge over a river.

Philipsburg Manor

8.2/10 (40 reviews)
You can find out about the history of Sleepy Hollow with a trip to Philipsburg Manor. Wander the riverfront in this quaint area.
See properties
A historic stone building with a tower and a black iron fence.

Old Dutch Church of Sleepy Hollow

8.6/10 (74 reviews)
You can learn about the history of Sleepy Hollow with a trip to Old Dutch Church of Sleepy Hollow. Wander the riverfront in this family-friendly area.
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What to do in Sleepy Hollow

Helicopter landing in a field in New York

Introductory Helicopter Flight Lesson from Westchester

CA $1,818
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 $771 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.

Explore a world of travel with Expedia

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