Sleepy Hollow Vacation Packages 2026 from $440

Sleepy Hollow flight + hotel vacation packages

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

Hyatt Regency Greenwich

$440

per person

Mar 26 - Mar 29

found 1 day ago

Roundtrip flight included

Orlando (MCO) to White Plains (HPN)

This smoke-free hotel includes 2 restaurants, an indoor pool, and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. There's a bar/lounge on site, and concierge services and wedding services are also provided.

Hampton Inn & Suites Yonkers

Northwest Yonkers

$575

per person

Mar 25 - Mar 29

found 1 day ago

Roundtrip flight included

Kansas City (MCI) to White Plains (HPN)

This hotel features a gym and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.

Cromwell Manor Inn

Save 100% on your flight

$606

per person

Mar 5 - Mar 8

found 23 hours ago

Roundtrip flight included

Orlando (MCO) to White Plains (HPN)

This bed & breakfast doesn't skimp on freebies - guests receive free cooked-to-order breakfast, free WiFi, and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. Dry cleaning, luggage storage, and concierge services are also on offer.

Courtyard by Marriott Yonkers Westchester County

Northwest Yonkers

$511

per person

Mar 26 - Mar 29

found 1 day ago

Roundtrip non-stop flight included

Orlando (MCO) to White Plains (HPN)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, a terrace, and a garden are also offered.

Top Sleepy Hollow hotels deals

Highbridge Hotel

1263 Edward L Grant Highway Bronx NY

Free Cancellation

Reserve now, pay when you stay

$70 nightly

$84 total

Jan 22 - Jan 23

Total with taxes and fees

A rooftop terrace is featured at this hotel, along with self parking. Guests will appreciate free perks like buffet breakfast and WiFi in public areas. Multilingual staff at the 24-hour front desk can provide around-the-clock assistance.

Breakfast included

Free WiFi

Radio Hotel

2420 Amsterdam Ave New York NY

Free Cancellation

Reserve now, pay when you stay

$119 nightly

$140 total

Feb 2 - Feb 3

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Valet parking, a coffee shop, and a snack bar/deli are also offered.

Pet friendly

Restaurant

Sonesta White Plains Downtown

66 Hale Ave White Plains NY

Free Cancellation

Reserve now, pay when you stay

$179 nightly

$205 total

Feb 14 - Feb 15

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Enjoy the 24-hour gym and perks like free airport pick-up.

Pool

Free airport shuttle

Homewood Suites by Hilton Teaneck Glenpointe

1 Glenwood Ave Ste A Teaneck NJ

Free Cancellation

Reserve now, pay when you stay

$152 nightly

$174 total

Feb 1 - Feb 2

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free valet parking. Relax with a drink at the bar/lounge and enjoy free perks like on-the-go breakfast and free self parking.

Pool

Breakfast included

Hilton Garden Inn Ridgefield Park

70 Challenger Road Ridgefield Park NJ

Free Cancellation

Reserve now, pay when you stay

$83 nightly

$95 total

Feb 12 - Feb 13

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 2 conference rooms, free WiFi in public areas, and express check-out. Enjoy the 24-hour gym and perks like free self parking.

Pool

Pet friendly

DoubleTree by Hilton Hotel Nanuet

425 E Route 59 Nanuet NY

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$108 total

Feb 1 - Feb 2

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.

Pool

Hot Tub

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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.

Popular places to visit

This mansion was built in 1838 and is situated on 65 acres on the Hudson river and was home to New York City Major William Paulding Jr., merchant George Merritt and railroad tycoon Jay Gould consecutively.

Lyndhurst Mansion

4.5/5(9 reviews)

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.

The original bridge of Sleepy Hollow where the headless horseman crossed to get to the other side.
Are you familiar with the American Folklore Legend?

Sleepy Hollow Cemetery

5/5(4 reviews)

Learn about the local history of Sleepy Hollow with a stop at Sleepy Hollow Cemetery. Wander the riverfront in this family-friendly area.

Tarrytown Lighthouse

You can learn about the history of Sleepy Hollow with a stop at Tarrytown Lighthouse. Stroll along the riverfront in this family-friendly area, or check out its top-notch restaurants.

Frequently asked questions

How much are vacation packages to Sleepy Hollow?

Travelocity offers flight and hotel vacation packages from an incredible $440. With such amazing deals, you'll be saying hello to Sleepy Hollow in a flash.

Where can I get the best vacation package deals for Sleepy Hollow?

You'll discover a terrific range of Sleepy Hollow package deals on Travelocity. With as many as 400 airlines and 1,000,000 properties across the globe, piecing together the ultimate escape will be a breeze.

Why should I purchase my Sleepy Hollow vacation bundle with Travelocity?

From incredible destinations to memorable experiences, we have everything you need to satisfy your travel desires. Our friendly 24/7 customer support will also make sure you're being taken care of before, during and after your getaway. And don't fret if you notice a cheaper price on your booking, we'll match it. That's our Price Match Guarantee.

Can I save on my Sleepy Hollow car rental if I book it with hotels and flights?

With a Sleepy Hollow vacation package, you can bundle your flight, car and hotel bookings and save a tidy sum. If you want to discover the best of this impressive destination, why not start with Liberty Bell Center? This top sight is 100 mi from Sleepy Hollow. With your own wheels, you'll be there in no time.

Which airport is best for Sleepy Hollow?

John F. Kennedy Intl. Airport (JFK) is one of the busiest airports in Sleepy Hollow. It's around 30 mi south of the downtown area. Other options open to you are Liberty Intl. Airport (EWR) (30 mi away from central Sleepy Hollow) and LaGuardia Airport (LGA) (20 mi away from central Sleepy Hollow).