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

3.5 out of 5
Downtown Stamford
Price was CA $966, price is now CA $727 per person
CA $727
per person
Dec 17 - Dec 20
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
8/10 Very good! (1,000 reviews)
This is an older property, but it was incredibly convenient for Hertz return and the staff were very helpful in getting us a room on a higher floor. The room was clean.

Reviewed on Oct 29, 2026

Luxury 3 BR Near NYC with Easy Parking

Luxury 3 BR Near NYC with Easy Parking

2 out of 5
Bryn Mawr
Price was CA $1,292, price is now CA $998 per person
CA $998
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
2/10 (1 review)
This is a scam and at the same time others guest’s was there for same booking but we can’t get any feed the property support and we returned from the property and kids suffered a lot!!!

Reviewed on Oct 12, 2026

Upscale Modern Luxury 3BR Home

Upscale Modern Luxury 3BR Home

2 out of 5
Save 100% on your flight
Price was CA $2,421, price is now CA $1,882 per person
CA $1,882
per person
Dec 9 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to White Plains (HPN)
4/10 (1 review)
Property was missing needed items and it took two days to get them(coffee maker). For the price you get what you’d expect. Older property with some updates needed. Everything worked but older appliances.

Reviewed on Jan 23, 2026

Uscale 2BR Escape in the Heart of NYC

Uscale 2BR Escape in the Heart of NYC

2 out of 5
Bryn Mawr
Price was CA $1,154, price is now CA $905 per person
CA $905
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
9/10 Wonderful! (2 reviews)
Safe location, looks newly restored. Neighbors upstairs they’re terrible walking all night and loud talking

Reviewed on Oct 27, 2026

Delamar Greenwich Harbor

Delamar Greenwich Harbor

4 out of 5
Price was CA $1,241, price is now CA $1,017 per person
CA $1,017
per person
Dec 13 - Dec 15
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
9.4/10 Exceptional! (1,002 reviews)

Ready to book your vacation to Sleepy Hollow?

 

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Sleepy Hollow Hotel Deals

Highbridge Hotel

Highbridge Hotel

2 out of 5
1263 Edward L Grant Highway Bronx NY
Fully refundableReserve now, pay when you stay
The price is CA $126 per night from Nov 9 to Nov 10
CA $126
CA $149 total
Nov 9 - Nov 10
includes taxes & fees
Highbridge Hotel
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 $184 per night from Nov 2 to Nov 3
CA $184
CA $254 total
Nov 2 - Nov 3
includes taxes & fees
Radio Hotel
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 $165 per night from Nov 1 to Nov 2
CA $165
CA $189 total
Nov 1 - Nov 2
includes taxes & fees
8/10 Very good! (1,605 reviews)
"The room was fine. The rest of the hotel is in need of renovation, which apparently is in progress."

Reviewed on Oct 30, 2026

Executive Inn - Fort Lee
See all 1,846 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

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
Open 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

What to do in Sleepy Hollow

Helicopter landing in a field in New York

Introductory Helicopter Flight Lesson from Westchester

CA $997
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 $727 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.