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.
Hotel NoMa, Trademark Collection by Wyndham

Hotel NoMa, Trademark Collection by Wyndham

3 out of 5
Price was CA $1,150, price is now CA $880 per person
CA $880
per person
Nov 14 - Nov 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
8/10 Very Good! (1,003 reviews)
What a Gem. The room spacious and clean ( tub definitely needs elbow grease but that’s why shower shoes are a thing). Overall, The entire team was amazing. It’s a resort like feeling North of Manhattan. THE FOOD OMG where to begin nothing let me down over the four nights!!!! Dominique, Nicole, and Teddy-and the locals who frequent are the reasons we will come back - NOMA SOCIAL just continue to play a variety of music becasue although I love my latin music it was overkill and DJ’s must represent rhe NYC culture to entirely with a good mix and not a centered focus on one genre- BUT STILL A FAVORITE PLACE!!

Reviewed on Aug. 20, 2025

Dome House Retreat

Dome House Retreat

4 out of 5
Price was CA $3,567, price is now CA $2,483 per person
CA $2,483
per person
Sep 26 - Oct 1
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
No reviews
Luxury NY Home 3BR with Easy Parking

Luxury NY Home 3BR with Easy Parking

3 out of 5
Southeast Yonkers
Price was CA $3,836, price is now CA $2,730 per person
CA $2,730
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to White Plains (HPN)
3/10 (4 reviews)
Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

3 out of 5
Price was CA $1,283, price is now CA $988 per person
CA $988
per person
Sep 27 - Oct 2
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to White Plains (HPN)
7.8/10 Good! (1,123 reviews)
Quiet friendly clean

Reviewed on Aug. 21, 2025

Luxury Living in the Heart of NY

Luxury Living in the Heart of NY

4 out of 5
Southeast Yonkers
Price was CA $4,102, price is now CA $3,168 per person
CA $3,168
per person
Nov 14 - Nov 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
2/10 (1 review)

Ready to book your vacation to Sleepy Hollow?

 

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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 $176 per night from Sep 1 to Sep 2
CA $176
CA $201 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (1,126 reviews)
"Pool not in service. Concrete around pool and walk to parking lot in poor shape. Excellent breakfast and well staffed"

Reviewed on Aug. 19, 2025

Hampton Inn White Plains/Tarrytown
Radio Hotel

Radio Hotel

4 out of 5
2420 Amsterdam Ave, New York, NY
Fully refundableReserve now, pay when you stay
The price is CA $207 per night from Sep 1 to Sep 2
CA $207
CA $272 total
Sep 1 - Sep 2
includes taxes & fees
8.6/10 Excellent! (2,638 reviews)
"Very nice"

Reviewed on Aug. 19, 2025

Radio Hotel
Ramada by Wyndham Rochelle Park Near Paramus

Ramada by Wyndham Rochelle Park Near Paramus

2 out of 5
375 W Passaic St, Rochelle Park, NJ
Fully refundableReserve now, pay when you stay
The price is CA $152 per night from Sep 21 to Sep 22
CA $152
CA $174 total
Sep 21 - Sep 22
includes taxes & fees
7.2/10 Good! (1,181 reviews)
"Attached to a great restaurant. Elevator is a little frightening and the room keys keep needing to be programmed. Comfortable room/bed. Good water pressure. Plenty of towels and closet space"

Reviewed on Aug. 17, 2025

Ramada by Wyndham Rochelle Park Near Paramus
See all 1,685 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 $922
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 $880 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.