Sleepy Hollow Packages (Flight + Hotel)

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Top hotels in Sleepy Hollow

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 ฿2,110 per night from 26 Jul to 27 Jul
฿2,110
฿2,538 total
26 Jul - 27 Jul
includes taxes & fees
9.2/10 Wonderful! (4,316 reviews)
"Room is spacious and clean. Staff are super helpful. Location is very convenient."

Reviewed on 14 Jul 2026

Highbridge Hotel
Crowne Plaza Englewood by IHG

Crowne Plaza Englewood by IHG

3.5 out of 5
401 S Van Brunt St Englewood NJ
Fully refundable
The price is ฿3,813 per night from 12 Aug to 13 Aug
฿3,813
฿4,370 total
12 Aug - 13 Aug
includes taxes & fees
8.2/10 Very good! (1,414 reviews)
"Loved it! Very friendly and accommodating."

Reviewed on 14 Jul 2026

Crowne Plaza Englewood by IHG
Armoni Inn & Suites

Armoni Inn & Suites

3.5 out of 5
329 Route 303 Orangeburg NY
Fully refundableReserve now, pay when you stay
The price is ฿3,285 per night from 19 Jul to 20 Jul
฿3,285
฿3,658 total
19 Jul - 20 Jul
includes taxes & fees
6.2/10 (2,281 reviews)
"Room are clean , but way to musty , Rugs in and out rooms need be shampooed. But for price not bad for a night!"

Reviewed on 14 Jul 2026

Armoni Inn & Suites
See all 1,876 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.

Stay near popular Sleepy Hollow attractions

A lighthouse with a metal bridge over water during sunset.
Photo by santosh dash
Open Photo by santosh dash

Tarrytown Lighthouse

8.4/10 (104 reviews)
This historic 1883 beacon on the Hudson River showcases a unique caisson design and maritime heritage. Climb its five stories to enjoy panoramic river views and glimpse the fascinating life of lighthouse keepers past.
See properties

What to do in Sleepy Hollow

Helicopter landing in a field in New York

Introductory Helicopter Flight Lesson from Westchester

฿42,706
per traveller
Introductory Helicopter Flight Lesson from Westchester
See all activities in Sleepy Hollow

Frequently asked questions

How much does a Sleepy Hollow holiday package cost?
You'll find cheap prices on Expedia for your Sleepy Hollow getaway. However, factors like the hotel choice, length of stay and season will influence how much your holiday to Sleepy Hollow costs.
What are the cheapest months to go to Sleepy Hollow?
If you're looking to book a cheap Sleepy Hollow holiday package, consider visiting in January, February and March. You're likely to find lower rates on flights and hotels during these months — perfect for budget-conscious travellers.
How many days is enough for Sleepy Hollow?
With a well-planned schedule, you can easily hit the main Sleepy Hollow sights in a few days. But if you'd like to discover hidden spots or take day trips, think about booking your Sleepy Hollow holiday for longer.
Is it worth booking a holiday package to Sleepy Hollow?
Sleepy Hollow has everything you need for an awesome trip — nature, culture and history are just the start. Whether you want to check out sights like Tarrytown Lighthouse and Old Dutch Church of Sleepy Hollow, or venture off the beaten track, you'll find plenty to see and do on your Sleepy Hollow holiday.
How to find the best Sleepy Hollow package deals?
Landing a cheap Sleepy Hollow package deal is easy with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget range, apply a few filters and browse what's available. You can customise your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to discover the most economical Sleepy Hollow package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Sleepy Hollow holiday as a package?
An Expedia holiday package could land you significant savings when compared to arranging flights and hotels separately. Better still, you can tailor your Sleepy Hollow getaway to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a holiday package to Sleepy Hollow?
If you've got your Sleepy Hollow travel dates finalized, book as early as you can to score some fantastic deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Sleepy Hollow?

  1. Pick your dates: What you'd like to do in Sleepy Hollow and your preferred season can help you decide when to go.
  2. Work out your budget: Make sure you have enough money to cover everything from transportation and food to flights and experiences. Your hotel will likely be the biggest expense during your trip to Sleepy Hollow.
  3. Decide how long to go away for: Now that you know more about Sleepy Hollow, you can figure out the right length of your break. Put together a rough plan and give yourself enough time for all the things you want to do.
  4. Combine your airfare and accommodation: After you've settled on your dates and duration, book the perfect Sleepy Hollow holiday package for you.

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.